Supporting Information. C2-Alkylation and Alkenylation of Indoles Catalyzed by a Low-Valent Cobalt Complex in the absence of Reductant
|
|
- ŌΣίμων Λούπης
- 6 χρόνια πριν
- Προβολές:
Transcript
1 Supporting Information C2-Alkylation and Alkenylation of Indoles Catalyzed by a Low-Valent Cobalt Complex in the absence of Reductant Brendan J. Fallon, [a] Etienne Derat, [a] Muriel Amatore, [a] Corinne Aubert, [a] Fabrice Chemla, [a] Franck Ferreira, [a] Alejandro Pérez-Luna, [a] and Marc Petit* [a] Institut Parisien de Chimie Moléculaire, UMR 8232, Université Pierre et Marie Curie-Paris 6, Case 229, 4 Place Jussieu, Paris, France List of the Contents of the Supporting Information I. General information. S2 II. Deuterium and mechanistic studies...s3 III. DFT calculations.. S6 IV. Preparation of starting materials. S18 V. Characterization of new compounds.s22 VI. 1 H NMR Spectra of products S45 VII. References. S86 S1
2 I. General information: Commercial reagents were purified prior to use following the guidelines of Perrin and Armarego. 1 Toluene was purified by mean of distillation under dry nitrogen atmosphere on benzophenone/sodium ketyl and degassed by sparging argon. Organic solutions were concentrated under reduced pressure on a Büchi rotary evaporatory. Chromatographic purifications of products were accomplished using force-flow chromatography on Davisil (LC60A) SI 60 Å (40 63 μm) silica gel according to the method of Still. 2 Thin layer chromatography (TLC) was performed on Merck 60 F254 silica gel plates. TLC visualization was performed by fluorescence quenching (λ = 254 nm), dipping in KMnO 4 or paraanisaldehyde stains. Filtrations through Celite were performed using Hyflo Super Cel from Fluka. 1 H NMR spectra were recorded on a Brucker 400 AVANCE or 300 AVANCE (400 and 300 MHz respectively) and are referenced relative to residual CDCl 3 protons signals at δ 7.26 ppm. 13 C NMR spectra were recorded on a Brucker 400 AVANCE or 300 AVANCE (100 and 75 MHz respectively) and are referenced relative to CDCl 3 at δ ppm. 19 F NMR spectra were recorded on a Brucker 400 AVANCE (376 MHz) and are referenced relative to CFCl 3 at δ 0.00 ppm. Data are reported as follows: chemical shift (δ ppm), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, qt = quintuplet, m = multiplet, bs = broad signal), coupling constant (Hz) and integration. IR spectra were recorded on a Bruker Tensor 27 (ATR diamond) and are reported in terms of frequency of absorption (cm-1). High-resolution Mass spectra were obtained from the Laboratoire Structure et Fonction de Molécules Bioactives (Université Pierre et Marie Curie, Paris 6). S2
3 III. Deuterium and mechanistic experiments: 1 H NMR Spectra of deuteriated and non deuteriated indoles 98% deuterium incorporation S3
4 (a) Deuterium labeling experiment (see scheme 2a in article) Sm. >98% D 0.78H 0.78H 2.47H 0.7H 0.78H 0.86H 22% % 2.47 Recovery of the starting material showed a significant decrease of the deuterium content (0.04 H to 0.7H). Deuterium was included into all TWO alkene position alpha and beta (0.78H). The desired product was isolated with a marginal (<20% ) incorporation of deuterium in the α position. Consistent with this observation the methyl group was substantially deuteriated >50% 63% 2.47 S4
5 (b) Hydrogen/Deuterium transfer study (see scheme 2b in article) Deuterium labeled indole 1a-d was reacted with diphenylacetylene 2a in the presence of 50 mol% HCo(PMe 3 ) 4. No hydrogen incorporation was observed in the final product. This result suggested that C-H bond activation and functionalization proceeded in a concerted manner for the hydro-complex. This hypothesis was further substantiated by DFT calculations. S5
6 (c) Competition experiment (see scheme 3a in article) S6
7 II. DFT Calculations XYZ coordinates CH activation with diphenylacetylene Reagent Co N C C C C C C C C C O C H H H H H H H H P C C C H H H H H H H H S7
8 H C C C C C C C C C C C C C C H H H H H H H H H H N C C C C C C C H H H H H H H H Transition state S8
9 Co N C C C C C C C C C O C H H H H H H H H P C C C H H H H H H H H H C C C C C C C C C C C S9
10 C C C H H H H H H H H H H N C C C C C C C H H H H H H H H Product Co N C C C C C C C C C O S10
11 C H H H H H H H H P C C C H H H H H H H H H C C C C C C C C C C C C C C H H H H H H H H H S11
12 H N C C C C C C C H H H H H H H H CH activation with styrene Reagent Co N C C C C C C C C C O C H H H H H H H H P S12
13 C C C H H H H H H H H H C C C C C C C C H H H H H N C C C C C C C H H H H H H H H H H H S13
14 Transition state Co N C C C C C C C C C O C H H H H H H H H P C C C H H H H H H H H H C C C C C C C C H S14
15 H H H H N C C C C C C C H H H H H H H H H H H Product Co N C C C C C C C C C O C H H H H H S15
16 H H H P C C C H H H H H H H H H C C C C C C C C H H H H H N C C C C C C C H H H H H H H H S16
17 H H H Energetic data diphenylacetylene E (u.a.) ZPC (u.a.) S DE (kcal/mol) DH (kcal/mol) DG (kcal/mol) Reagent TS Product Styrene E (u.a.) ZPC (u.a.) S DE (kcal/mol) DH (kcal/mol) DG (kcal/mol) Reagent TS Product S17
18 Iv. Preparation of starting materials: General procedure (A) for the preparation of indole precursors: Indole precursors were prepared through N-alkylation of indole-3-carboxaldehyde with methyl iodide, benzyl bromide or alkyl bromide with NaH as base in DMF. The corresponding carbonyl compounds were condensed with para-anisidine in toluene with MS 4Å to afford the corresponding indole substrates which were purified by precipitation from pentane/et 2 O. The 1 H NMR spectrum of all compounds showed good agreement with the literature data. (E)-N-(4-Methoxyphenyl)-1-(1-methyl-1H-indol-3-yl)methanimine (1a) 3 (E)-N-(4-Methoxyphenyl)-1-(1-methyl-1H-indol-3-yl-2-d)methanimine (1a-d) 3 (E)-1-(1-Benzyl-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (1b) 3 (E)-1-(5-Methoxy-1-methyl-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (1d) 3 (E)-1-(5-Fluoro-1-methyl-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (1h) 3 (E)-1-(1-(But-3-en-1-yl)-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (4a) 4 (E)-1-(1-((E)-Hex-3-en-1-yl)-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (4c) 4 (E)-N-(4-Methoxyphenyl)-1-(1-(2-methylbut-3-en-1-yl)-1H-indol-3-yl)methanimine (4d) 4 (E)-1-(1,7-Dimethyl-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (1c) Pale yellow solid (53 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.64 (s, 1H), 8.35 (ddd, J = 7.9, 1.4, 0.7 Hz, 1H), 7.42 (s, 1H), (m, 2H), 7.16 (dd, J = 7.9, 7.2 Hz, 1H), 7.03 (dt, J = 7.1, 1.1 Hz, 1H), (m, 2H), 4.11 (s, 3H), 3.86 (s, 3H), 2.79 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.3, 152.6, 146.7, 135.5, 135.2, 127.2, 125.9, 123.1, (2C), 121.6, 121.3, 120.0, (2C), 55.5, 37.3, IR (thin film): max = 2989, 1619, 1545, 1242, 744 cm -1. HRMS (ESI): calculated for C 18 H 19 N 2 O [M+ H] + : ; found S18
19 (E)-1-(5-(Benzyloxy)-1-methyl-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (1e) White solid (44 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.63 (s, 1H), 8.16 (d, J = 2.5 Hz, 1H), 7.55 (m, 2H), (m, 3H), (m, 1H), (m, 3H), 7.08 (dd, J = 8.9, 2.5 Hz, 1H), (m, 2H), 5.21 (s, 2H), 3.87 (s, 3H), 3.82 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 154.8, 152.7, 146.7, 137.5, 134.3, 133.1, (2C), (2C), 127.7, 126.5, (2C), 114.7, (2C), 114.0, 110.2, 105.4, 70.7, 55.5, IR (thin film): max = 2978, 1598, 1467, 1376, 1250, 1052, 896 cm -1. HRMS (ESI): calculated for C 24 H 23 N 2 O 2 [M+ H] + : ; found Methyl (E)-3-(((4-methoxyphenyl)imino)methyl)-1-methyl-1H-indole-6-carboxylate (1f) white solid (44 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.67 (s, 1H), 8.50 (dd, J = 8.4, 0.7 Hz, 1H), 8.15 (dd, J = 1.5, 0.7 Hz, 1H), 7.99 (dd, J = 8.4, 1.4 Hz, 1H), 7.70 (s, 1H), (m, 2H), (m, 2H), 3.99 (s, 3H), 3.94 (s, 3H), 3.86 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 167.8, 157.6, 151.9, 148.8, 137.3, 136.2, , 124.8, 122.4, (2C), 121.7, (2C), 111.8, 55.5, 52.1, IR (thin film): max = 2946, 1701, 1594, 1500, 1266, 891, 879 cm -1. HRMS (ESI): calculated for C 19 H 19 N 2 O 3 [M+ H] + : ; found (E)-1-(5-Isocyano-1-methyl-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (1g) yellow solid (73 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.96 (dd, J = 1.6, 0.7 Hz, 1H), 8.63 (s, 1H), (m, 2H), 7.41 (dd, J = 8.6, 0.7 Hz, 1H), (m, 2H), (m, 2H), 3.90 (s, 3H), 3.87 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.8, 151.1, 145.6, 139.2, 135.4, 128.4, 126.2, 125.6, (2C), 120.4, 115.9, (2C), 110.3, 104.6, 55.5, IR (thin film): max = 3289, 2938, 2217, 1623, 1539, 1388, 1121, 834 cm -1. HRMS (ESI): calculated for C 18 H 16 N 3 O [M+ H] + : ; found S19
20 (E)-1-(6-Chloro-1-methyl-1H-indol-3-yl)-N-(4- methoxyphenyl)methanimine (1i) Yellow solid (60 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.60 (s, 1H), 8.45 (dd, J = 8.5, 0.5 Hz, 1H), 7.45 (s, 1H), 7.35 (dd, J = 1.8, 0.6 Hz, 1H), (m, 1H), (m, 2H), (m, 2H), 3.86 (s, 3H), 3.80 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , (2C), , (2C), , 55.52, IR (thin film): max = 2966, 1987, 1564, 1480, 1104, 811 cm -1. HRMS (ESI): calculated for C 17 H 16 N 2 OCl [M+ H] + : ; found (E)-1-(1-(But-3-en-1-yl)-1H-indol-3-yl)-N-(4-methoxyphenyl)ethan-1-imine (4b) Orange solid (53 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), 7.64 (s, 1H), (m, 3H), (m, 2H), (m, 2H), 5.70 (m, 1H), (m, 2H), (m, 2H), 3.66 (s, 3H), 2.54 (m, 2H), 2.44 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 161.8, 155.4, 145.4, 137.0, 134.2, 131.0, 123.5, 122.7, (2C), 117.8, 117.1, 116.6, (2C), 109.4, 60.4, 55.5, 46.2, 34.3, IR (thin film): max = 2936, 1636, 1526, 1465, 1340, 823 cm -1. HRMS (ESI): calculated for C 21 H 23 N 2 O [M+ H] + : ; found S20
21 (E)-1-(1-(But-3-en-1-yl)-5-methoxy-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (4e) Yellow solid (41 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.54 (s, 1H), 7.93 (d, J = 2.6 Hz, 1H), 7.42 (s, 1H), (m, 3H), (m, 3H), 5.70 (dd, J = 17.3, 10.0 Hz, 1H), (m, 2H), 4.11 (t, J = 7.1 Hz, 2H), 3.84 (s, 3H), 3.76 (s, 3H), 2.53 (m, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 155.6, 152.8, 146.8, 134.0, 133.1, 132.1, 126.7, (2C), 118.0, 116.4, (2C), 113.4, 110.4, 103.8, 55.8, 55.5, 46.5, IR (thin film): max = 3011, 2937, 1616, 1499, 1288, 1104, 745 cm -1. HRMS (ESI): calculated for C 21 H 23 N 2 O 2 [M+ H] + : ; found Methyl (E)-1-(but-3-en-1-yl)-3-(((4-methoxyphenyl)imino)methyl)-1H-indole-6-carboxylate (4f) Yellow solid (41 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.58 (s, 1H), 8.41 (dd, J = 8.4, 0.7 Hz, 1H), 8.07 (dd, J = 1.5, 0.7 Hz, 1H), 7.95 (dd, J = 8.4, 1.4 Hz, 1H), 7.62 (s, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), 4.23 (t, J = 7.1 Hz, 2H), 3.90 (s, 3H), 3.77 (s, 3H), (m, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 167.8, 162.0, 152.0, (2C), 135.1, 133.6, 129.7, 125.1, 124.8, 122.4, (2C), 118.3, 115.3, (2C), 111.9, 55.5, 52.1, 46.5, IR (thin film): max = 2947, 1706, 1616, 1535, 1462, 1286, 878, 789 cm -1. HRMS (ESI): calculated for C 22 H 23 N 2 O 3 [M+ H] + : ; found Synthesis of catalysts: Co(PMe 3 ) 4 and HCo(PMe 3 ) 4 were synthesised according to literature methods and showed good agreement with the literature data. 5,6 Note care should be taken when handling these catalysts as they are combustible in air. S21
22 V. Characterization of new compounds. General procedure B: Cobalt catalysed hydroarylation of internal alkynes: To a sealed tube under argon were added Co(PMe 3 ) 4 (5 mol %), imine (0.5mmol) and alkyne (0.6 mmol). Degassed toluene (1 ml) was added and the resulting solution was heated at 170 C for 1 h in the microwave (absorption level normal). The reaction mixture was then filtered through a plug of celite washing with ethyl acetate (3 x 10 ml). The crude product was purified by silica chromatography to yield the desired product. (E)-1-(2-((Z)-1,2-Diphenylvinyl)-1-methyl-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (3aa) 7 The general procedure (B) was applied to (E)-N-(4-methoxyphenyl)-1-(1- methyl-1h-indol-3-yl)methanimine (1a, mg, 0.50 mmol, 1.0 eq.) and diphenylacetylene (2a, mg, 0.60 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 80/20) afforded the title compound (3aa) as a yellow solid (218.7 mg, 99 %). mp; o C. 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), 8.38 (s, 1H), 7.51 (s, 1H), (m, 8H), (m, 3H), (m, 2H), (m, 2H), (m, 2H), 3.79 (s, 3H), 3.49 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.1, 153.7, 146.8, 143.7, 140.9, 137.9, 135.9, 134.4, 129.7, (2C), (2C), (2C), 128.2, 128.2, (2C), 125.7, 123.3, 123.1, 121.9, (2C), (2C), 112.8, 109.5, 55.4, IR (thin film): max = 3055, 2934, 1615, 1500, 1243, 1076, 777, 695 cm -1. HRMS (ESI): calculated for C 31 H 26 N 2 O [M+ H] + : ; found (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-((Z)-1-phenyl-2-(trimethylsilyl)vinyl)-1H-indol-3- yl)methanimine (3ab) The general procedure (B) was applied to (E)-N-(4-methoxyphenyl)-1-(1- methyl-1h-indol-3-yl)methanimine (1a, mg, 0.50 mmol, 1.0 eq.) and trimethyl(phenylethynyl)silane (2b, mg, 0.60 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 80/20) afforded the title compound (3ab) as a yellow oil (202.1 mg, 92 %) as a mixture of stereoisomers 90/10 S22
23 anti/syn as determined by 1 H NMR. The characteristic peaks for the minor isomer as determined by 1 H NMR are as follows: δ 6.23 (s, 1H), 3.83 (s, 3H), 3.41 (s, 3H). Major isomer: 1 H NMR (400 MHz, CDCl 3 ) δ 8.76 (ddd, J = 6.6, 3.0, 1.8 Hz, 1H), 8.51 (s, 1H), (m, 8H), (m, 2H), 6.99 (s, 1H), (m, 2H), 3.81 (s, 3H), 3.49 (s, 3H), (s, 9H). 13 C NMR (100 MHz, CDCl 3 ) δ 158.0, 154.9, 147.7, 146.4, 145.3, 141.0, 138.5, 138.2, (2C), 129.4, (2C), 126.3, 124.1, 124.1, (2C), 122.7, (2C), 115.1, 110.1, 56.3, 31.2, 0.0 (3C). IR (thin film): max = 2951, 1615, 1574, 1499, 1464, 1242, 909 cm -1. HRMS (ESI): calculated for C 31 H 26 N 2 O [M+ H] + : ; found (Z)-1-Methyl-2-(1-phenylhex-1-en-1-yl)-1H-indole-3-carbaldehyde (3ac) A modified version of procedure (B) was applied to (E)-N-(4-methoxyphenyl)- 1-(1-methyl-1H-indol-3-yl)methanimine (1a, mg, 0.50 mmol, 1.0 eq.) and hex-1-yn-1-ylbenzene (2c, 95 mg, 0.60 mmol, 1.2 eq.). The resulting mixture was quenched with 3M HCl (1.0 ml). The resulting mixture was then stirred at room temperature for 1 h, and then extracted with ethyl acetate (3 x 10 ml). The combined organic layer was dried over MgSO 4 and concentrated under reduced pressure. Silica gel chromatography (eluent pentane/etoac 80/20) afforded the title compound (3ac) as a yellow oil (218.7 mg, 65 %) as a mixture of stereoisomers 88/12 anti/syn as determined by 1 H NMR. The characteristic peaks for the minor isomer as determined by 1 H NMR are as follows: δ 9.89 (s, 1H), 6.06 (t, J = 7.5 Hz, 1H). Major Isomer: 1 H NMR (400 MHz, CDCl 3 ) δ 9.77 (s, 1H), (m, 1H), (m, 6H), (m, 1H), (m, 1H), 6.64 (t, J = 7.5 Hz, 1H), 3.42 (d, J = 1.2 Hz, 3H), 2.02 (m, J = 7.4 Hz, 2H), (m, 4H), 0.77 (t, J = 7.3 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 186.1, 149.3, 138.9, 138.0, 129.1, 128.8, 128.6, (2C), 127.9, (2C), 125.1, 123.6, 123.1, 122.2, 115.8, 109.7, 31.3, 30.3, 22.3, IR (thin film): max = 2929, 1652, 1464, 1382, 1046, 751 cm -1. HRMS (ESI): calculated for C 22 H 23 NNaO [M+ H] + : ; found S23
24 (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-((Z)-1-(pyridin-3-yl)-2-(trimethylsilyl)vinyl)-1Hindol-3-yl)methanimine (3ad) The general procedure (B) was applied to (E)-N-(4-methoxyphenyl)-1- (1-methyl-1H-indol-3-yl)methanimine (1a, mg, 0.50 mmol, 1.0 eq.) and 3-((trimethylsilyl)ethynyl)pyridine (2d, mg, 0.60 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 75/25) afforded the title compound (3ad) as a yellow oil (217.3 mg, 99 %). 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 1H), 8.52 (dd, J = 4.8, 1.6 Hz, 1H), 8.49 (s, 1H), 7.48 (ddd, J = 8.0, 2.4, 1.6 Hz, 1H), (m, 3H), (m, 3H), 7.07 (s, 1H), (m, 2H), 3.80 (s, 3H), 3.50 (s, 3H), (s, 9H). 13 C NMR (100 MHz, CDCl 3 ) δ 158.3, 154.3, 150.4, 148.3, 147.6, 144.8, 142.6, 141.3, 138.3, 136.7, 134.3, 126.4, 124.5, 124.4, 124.2, 123.0, (2C), 115.6, (2C), 110.3, 56.4, 31.3, -0.0 (3C). IR (thin film): max = 2951, 1615, 1498, 1464, 1437, 1408, 1241, 1034, 835, 748 cm -1. HRMS (ESI): calculated for C 27 H 30 N 3 OSi [M+ H] + : ; found (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-((Z)-1-phenyl-2-(trimethylsilyl)vinyl)-1H-indol-3- yl)methanimine (3ae) The general procedure (B) was applied to (E)-N-(4-methoxyphenyl)-1-(1- methyl-1h-indol-3-yl)methanimine (1a, mg, 0.50 mmol, 1.0 eq.) and oct-4-yne (2e, 66.3 mg, 0.60 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 90/10) afforded the title compound (3ae) as a yellow oil (185.1 mg, 99 %) as a mixture of stereoisomers 79/21 anti/syn as determined by 1 H NMR. The characteristic peaks for the minor isomer as determined by 1 H NMR are as follows: δ 8.67 (s, 1H), 5.80 (t, J = 7.4 Hz, 1H). Major isomer: 1 H NMR (400 MHz, CDCl 3 ) δ 8.79 (m, 1H), 8.58 (s, 1H), (m, 3H), (m, 2H), (m, 2H), 6.09 (m, 1H), 3.92 (s, 3H), 3.75 (d, J = 6.2 Hz, 3H), (m, 2H), 1.96 (m, 1H), (m, 4H), 1.12 (m, 1H), 1.02 (m, 3H), 0.92 (t, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.1, 154.0, 147.3, 146.2, 137.6, 135.9, 130.1, S24
25 125.6, 122.7, 122.7, (2C), 121.6, (2C), 112.1, 109.2, 55.5, 41.0, 31.8, 30.3, 22.4, 21.5, 13.9, IR (thin film): max = 2956, 2869, 1614, 1498, 1463, 1370, 1241, 1035, 747 cm -1. HRMS (ESI): calculated for C 25 H 31 N 2 O [M+ H] + : ; found (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-((Z)-1-phenyl-2-(trimethylsilyl)vinyl)-1H-indol-3- yl)methanimine (3af) The general procedure (B) was applied to (E)-N-(4-methoxyphenyl)-1- (1-methyl-1H-indol-3-yl)methanimine (1a, mg, 0.50 mmol, 1.0 eq.) and dec-5-yne (2f, 83.1 mg, 0.60 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 90/10) afforded the title compound (3af) as a yellow oil (164.4 mg, 82 %) as a mixture of stereoisomers 78/22 anti/syn as determined by 1 H NMR. The characteristic peaks for the minor isomer as determined by 1 H NMR are as follows: δ 8.63 (s, 1H), 5.76 (s, 1H). Major isomer: 1 H NMR (400 MHz, CDCl 3 ) δ 8.75 (m, 1H), 8.55 (d, J = 0.8 Hz, 1H), (m, 3H), (m, 2H), (m, 2H), 6.05 (m, 1H), 3.89 (s, 3H), 3.72 (d, J = 5.8 Hz, 3H), (m, 2H), (m, 2H), (m, 7H), 1.06 (m, 1H), (m, 3H), (m, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.1, 154.0, 147.3, 146.2, 137.6, 136.0, 130.1, 125.6, 122.7, 122.6, (2C), 121.6, (2C), 112.1, 109.2, 55.5, 38.6, 31.5, 30.4, 30.3, 29.5, 22.5, 22.3, 13.9, IR (thin film): max = 2926, 1614, 1498, 1463, 1436, 1240, 1103, 747 cm -1. HRMS (ESI): calculated for C 27 H 35 N 2 O [M+ H] + : ; found General procedure (C) : Cobalt catalysed intermolecular hydroarylation of alkenes: To a sealed tube under argon were added Co(PMe 3 ) 4 (10 mol %), imine (0.5mmol) and alkene ( mmol). Degassed toluene (1 ml) was added and the resulting solution was heated at 170 C for 1 h in the microwave (absorption level normal). The reaction mixture was then filtered through a plug of celite washing with ethyl acetate (3 x 10 ml). The crude product was purified by silica chromatography to yield the desired product. S25
26 (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-(1-phenylethyl)-1H-indol-3-yl)methanimine (3ag) The general procedure (C) was applied to (E)-N-(4-methoxyphenyl)-1- (1-methyl-1H-indol-3-yl)methanimine (1a, 132 mg, 0.50 mmol, 1.0 eq.) and styrene (2g, 62 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 90/10) afforded the title compound (3ag) as a yellow foam (182 mg, 99 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.79 (s, 1H), (m, 1H), (m, 8H), (m, 2H), (m, 2H), 5.15 (q, J = 7.4 Hz, 1H), 3.85 (s, 3H), 3.50 (s, 3H), 1.89 (d, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 δ 157.2, 153.0, 148.2, 147.1, 141.9, 137.6, (2C), (2C), 126.5, 125.9, 122.7, 122.2, (2C), 121.6, (2C), 111.8, 108.8, 55.5, 34.5, 30.9, IR (thin film): max = 3053, 2940, 1613, 1498, 1242, 783 cm -1. HRMS (ESI): calculated for C 25 H 25 N 2 O [M+ H] + : ; found (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-(1-(p-tolyl)ethyl)-1Hindol-3-yl)methanimine (3ah) The general procedure (C) was applied to (E)-N-(4- methoxyphenyl)-1-(1-methyl-1h-indol-3-yl)methanimine (1a, 132 mg, 0.50 mmol, 1.0 eq.) and 1-methyl-4-vinylbenzene (2h, 70 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography on silica (eluent pentane/etoac 90/10) afforded the title compound (3ah) as a yellow oil (182 mg, 99 %). 1 H NMR (400 MHz, CDCl 3 ) δ 8.77 (s, 1H), (m, 1H), (m, 3H), (m, 6H), (m, 2H), 5.10 (q, J = 8 Hz, 1H), 3.83 (s, 3H), 3.49 (s, 3H), 2.35 (d, J = 0.7 Hz, 3H), 1.85 (d, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 153.1, 148.5, 147.2, 138.9, 137.6, 136.1, (2C), (2C), 125.9, 122.6, 122.3, (2C), 121.6, (2C), 111.8, 108.8, 55.5, 34.2, 30.9, 20.9, IR (thin film): max = 2936, 1612, 1574, 1497, 1240, 1061, 964, 777 cm -1. HRMS (ESI): calculated for C 26 H 26 N 2 O [M+ H] + : ; found S26
27 (E)-N-(4-Methoxyphenyl)-1-(2-(1-(3-methoxyphenyl)ethyl)-1- methyl-1h-indol-3-yl)methanimine (3ai) The general procedure (C) was applied to (E)-N-(4- methoxyphenyl)-1-(1-methyl-1h-indol-3-yl)methanimine (1a, 132 mg, 0.50 mmol, 1.0 eq.) and 1-methoxy-3-vinylbenzene (2i, 68 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography on silica (eluent pentane/etoac 85/15) afforded the title compound (3ai) as a yellow oil (179.6 mg, 90 %). 1 H NMR (400 MHz, CDCl 3 ) δ 8.81 (s, 1H), (m, 1H), 7.29 (dt, J = 16.3, 5.8 Hz, 4H), 7.20 (d, J = 8.4 Hz, 2H), (m, 4H), 6.82 (d, J = 8.5 Hz, 1H), 5.13 (d, J = 7.4 Hz, 1H), 3.86 (s, 3H), 3.79 (s, 3H), 3.52 (s, 3H), 1.87 (d, J = 7.3 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 160.0, 157.2, 152.9, 148.0, 147.2, 143.7, 137.6, 129.7, 125.9, (2C), 122.2, 121.8, 121.6, 119.6, (2C), 113.5, 111.8, 111.3, 108.8, 55.5, 55.2, 34.5, 31.0, IR (thin film): max = 2939, 1612, 1499, 1468, 1242, 1035, 912, 749 cm -1. HRMS (ESI): calculated for C 26 H 27 N 2 O 2 [M+ H] + : ; found (E)-N-(4-Methoxyphenyl)-1-(2-(1-(2-methoxyphenyl)ethyl)-1-methyl-1H-indol-3- yl)methanimine (3aj) The general procedure (C) was applied to (E)-N-(4-methoxyphenyl)-1-(1-methyl-1H-indol-3- yl)methanimine (1a, 132 mg, 0.50 mmol, 1.0 eq.) and 1-methoxy-2-vinylbenzene (2j, 83 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography on silica (eluent pentane/etoac 90/10) afforded a mixture of the title compound (3aj) and the product of linear addition as a yellow foam (169 mg, 85 %). The branched/linear ratio was determined to be 76/24 by 1 H NMR. S27
28 Characteristic peaks for the linear product are 3.33 (t, J = 7.8 Hz, 2H) and 3.03 (t, J = 7.8 Hz, 2H). Note: NMR signals are only assigned to the major isomer. mp C 1 H NMR (400 MHz, CDCl 3 ) δ 8.78 (s, 1H), (m, 1H), (m, 1H), (m, 5H), (m, 3H), (m, 2H), 4.96 (q, J = 7.4 Hz, 1H), 3.85 (s, 3H), 3.78 (s, 3H), 3.68 (s, 3H), 1.84 (d, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 157.0, 154.0, 149.1, 147.3, 137.1, 130.8, 128.1, 127.2, 126.0, 122.8, 122.2, (2C), 121.8, 121.4, 120.4, (2C), 111.0, 110.8, 108.7, 55.4, 31.0, 30.1, IR (thin film): max = 2936, 1592, 1497, 1242, 1033, 748 cm -1. HRMS (ESI): calculated for C 26 H 27 N 2 O 2 [M+ H] + : ; found (E)-1-(2-(1-(4-Fluorophenyl)ethyl)-1-methyl-1H-indol-3-yl)-N-(4- methoxyphenyl)methanimine (3ak) The general procedure (C) was applied to (E)-N-(4-methoxyphenyl)- 1-(1-methyl-1H-indol-3-yl)methanimine (1a, 132 mg, 0.50 mmol, 1.0 eq.) and 1-fluoro-4-vinylbenzene (2k, 73 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography on silica (eluent pentane/etoac 90/10) afforded the title compound (3ak) as a yellow oil (162.6 mg, 84 %). 1 H NMR (400 MHz, CDCl 3 ) δ 8.67 (s, 1H), (m, 1H), (m, 3H), (m, 5H), (m, 2H), (m, 2H), (m, 2H), 5.06 (q, J = 7.9 Hz, 1H), 3.38 (s, 3H), 1.77 (d, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = Hz), 157.3, 152.7, 147.7, 147.1, (d, J = 3.2 Hz), 137.6, (d, J = 7.9 Hz), (d, J = 8.0 Hz), 125.9, 122.8, 122.2, (2C), 121.7, 115.6, 115.3, (2C), 111.8, 108.8, 55.5, 33.9, 30.9, F NMR (376 MHz, CDCl 3 ) δ IR (thin film): max = 2939, 1574, 1439, 1179, 1003, 831, 778 cm -1 HRMS (ESI): calculated for C 25 H 23 N 2 OF [M+ H] + : ; found S28
29 (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-(1-(naphthalen-2- yl)ethyl)-1h-indol-3-yl)methanimine (3al) The general procedure (C) was applied to (E)-N-(4- methoxyphenyl)-1-(1-methyl-1h-indol-3-yl)methanimine (1a, 132 mg, 0.50 mmol, 1.0 eq.) and 2-vinylnaphthalene (2l, 93 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography on silica (eluent pentane/etoac 90/10) afforded the title compound (3al) as a yellow oil (136.0 mg, 65 %). 1 H NMR (400 MHz, CDCl 3 ) δ 8.81 (s, 1H), (m, 1H), (m, 3H), 7.77 (d, J = 8.6 Hz, 1H), (m, 2H), (m, 4H), (m, 2H), (m, 2H), 5.28 (q, J = 7.3 Hz, 1H), 3.81 (s, 3H), 3.48 (s, 3H), 1.98 (d, J = 7.3 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 153.0, 147.9, 147.1, 139.5, 137.7, 133.4, 132.1, 128.4, 127.8, 127.6, 126.3, 126.1, 125.9, 125.8, 124.8, 122.7, 122.2, (2C), 121.7, (2C), 111.9, 108.8, 55.5, 34.8, 30.9, IR (thin film): max = 3003, 1677, 1468, 1106, 908, 730 cm -1 HRMS (ESI): calculated for C 29 H 26 N 2 O [M+ H] + : ; found (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-(1-phenylpropyl)-1H-indol-3-yl)methanimine (3am) The general procedure (C) was applied to (E)-N-(4- methoxyphenyl)-1-(1-methyl-1h-indol-3-yl)methanimine (1a, 132 mg, 0.50 mmol, 1.0 eq.) and (E)-prop-1-en-1-ylbenzene (2m, 78 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 70/30) afforded the title compound (3am) as a yellow oil (105.3 mg, 55 %). 1 H NMR (400 MHz, CDCl 3 ) δ 8.85 (s, 1H), (m, 1H), (m, 8H), (m, 2H), (m, 2H), 4.87 (dd, J = 10.2, 5.9 Hz, 1H), 3.86 (s, 3H), 3.53 (s, 3H), 2.55 (m, 1H), 2.24 (m, 1H), 1.05 (t, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 153.2, 147.2, 146.5, 141.4, 137.6, (2C), (2C), 126.6, 125.9, 122.6, 122.3, (2C), 121.6, (2C), S29
30 113.3, 108.8, 55.5, 42.2, 30.9, 25.6, IR (thin film): max = 2962, 1613, 1240, 1150, 806 cm -1. HRMS (ESI): calculated for C 26 H 27 N 2 O [M+ H] + : ; found (E)-N-(4-Methoxyphenyl)-1-(1-methyl-2-(1-(pyridin-4-yl)ethyl)-1H-indol-3-yl)methanimine (3an) The general procedure (C) was applied to (E)-N-(4-methoxyphenyl)-1- (1-methyl-1H-indol-3-yl)methanimine (1a, 132 mg, 0.50 mmol, 1.0 eq.) and 4-vinylpyridine (2n, 65 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 70/30) afforded the title compound (3an) as a yellow foam (182 mg, 99 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.65 (s, 1H), 8.46 (m, 3H), (m, 3H), 7.11 (dt, J = 4.6, 1.2 Hz, 2H), (m, 2H), (m, 2H), (m, 1H), 3.71 (s, 3H), 3.36 (s, 3H), 1.76 (d, J = 7.3 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.4, 152.2, 151.3, (2C), 146.8, 145.7, 137.5, 126.0, (2C), (2C), (3C), (2C), 112.1, 109.0, 55.5, 34.1, 31.1, IR (thin film): max =2941, 1612, 1440, 1241, 1061, 749, 730 cm -1. HRMS (ESI): calculated for C 24 H 24 N 3 O [M+ H] + : ; found (E)-1-(1-Benzyl-2-(1-phenylethyl)-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (3bg) The general procedure (C) was applied to (E)-1-(1-benzyl-1Hindol-3-yl)-N-(4-methoxyphenyl)methanimine (1b, 170 mg, 0.50 mmol, 1.0 eq.) and styrene (2g, 62 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 85/15) afforded the title compound (3bg) as a yellow solid (204 mg, 92 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 11H), (m, 2H), (m, 2H), (m, 2H), 5.16 (s, 2H), 4.84 (q, J = 7.3 Hz, 1H), 3.73 (s, 3H), 1.61 (d, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 153.3, 148.5, 147.0, 142.2, 137.3, 136.8, (2C), (2C), 127.4, (2C), 126.6, 126.2, (2C), 123.0, 122.6, 121.9, (2C), (2C), 112.2, 109.7, 55.5, 47.3, 35.1, IR (thin film): max = 3056, 1614, S30
31 1423, 1105, 695 cm -1. HRMS (ESI): calculated for C 31 H 29 N 2 O [M+ H] + : ; found (E)-1-(1,7-Dimethyl-2-(1-phenylethyl)-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (3cg) The general procedure (C) was applied (E)-1-(1,7-dimethyl- 1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine (1c, 139 mg, 0.50 mmol, 1.0 eq.) and styrene (2g, 62 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 80/20) afforded the title compound (3cg) as a yellow oil (96 mg, 50 %). 1 H NMR (400 MHz, CDCl 3 ) δ 8.68 (s, 1H), 8.46 (ddd, J = 8.0, 1.3, 0.7 Hz, 1H), (m, 5H), (m, 3H), 6.90 (dt, J = 7.1, 1.2 Hz, 1H), (m, 2H), 5.11 (q, J = 7.4 Hz, 1H), 3.74 (s, 3H), 3.65 (s, 3H), 2.66 (s, 3H), 1.78 (d, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.1, 153.0, 148.5, 147.2, 142.1, 136.4, (2C), (2C), 126.4, 126.9, 126.2, (2C), 121.6, 120.6, 120.1, (2C), 111.7, 55.5, 34.3, 34.1, 20.7, IR (thin film): max = 2928, 1613, 1538, cm -1.. HRMS (ESI): calculated for C 26 H 27 N 2 O [M+ H] + : ; found (E)-1-(5-Methoxy-1-methyl-2-(1-phenylethyl)-1H-indol-3- yl)-n-(4-methoxyphenyl)methanimine (3dg) The general procedure (C) was applied (E)-1-(5-methoxy-1- methyl-1h-indol-3-yl)-n-(4-methoxyphenyl)methanimine (1d, 139 mg, 0.50 mmol, 1.0 eq.) and styrene (2g, 62 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 80/20) afforded the title compound (3dg) as a yellow oil (189 mg, 95 %). 1 H NMR (400 MHz, CDCl 3 ) δ 8.64 (s, 1H), 8.14 (d, J = 2.5 Hz, 1H), (m, 5H), (m, 3H), (m, 3H), 4.93 (q, J = 7.3 Hz, 1H), 3.83 (s, 3H), 3.72 (s, 3H), 3.35 (s, 3H), 1.75 (d, J = 7.4 Hz, 3H). S31
32 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 155.9, 153.1, 148.6, 147.2, 142.0, 132.7, (2C), (2C), 126.6, 126.4, (2C), (2C), 112.7, 111.6, 109.6, 104.3, 55.9, 55.5, 34.6, 31.0, IR (thin film): max = 3085, 1558, 1158, 1028, 885, 718 cm -1.. HRMS (ESI): calculated for C 26 H 27 N 2 O 2 [M+ H] + : ; found (E)-1-(5-(Benzyloxy)-1-methyl-2-(1-phenylethyl)-1H-indol-3-yl)-N-(4- methoxyphenyl)methanimine (3eg) The general procedure (C) was applied to (E)-1-(5- (benzyloxy)-1-methyl-1h-indol-3-yl)-n-(4- methoxyphenyl)methanimine (1e, 186 mg, 0.50 mmol, 1.0 eq.) and styrene (2g, 62 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 85/15) afforded the title compound (3eg) as a yellow foam (234 mg, 99 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.77 (s, 1H), 8.38 (d, J = 2.6 Hz, 1H), (m, 2H), 7.43 (t, J = 7.5 Hz, 2H), (m, 6H), 7.19 (t, J = 8.3 Hz, 3H), 7.05 (dd, J = 8.8, 2.6 Hz, 1H), (m, 2H), 5.23 (s, 2H), 5.07 (q, J = 7.3 Hz, 1H), 3.87 (s, 3H), 3.49 (s, 3H), 1.89 (d, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.2, 155.0, 153.0, 148.6, 147.2, 142.0, 137.7, 132.8, (2C), (2C), (2C), 127.7, (2C), 126.6, 126.4, (2C), (2C), 113.3, 111.6, 109.6, 105.8, 70.8, 55.5, 34.6, 31.0, IR (thin film): max = 3031, 1612, 1497, 1288, 1105, 735 cm -1. HRMS (ESI): calculated for C 32 H 31 N 2 O 2 [M+ H] + : ; found Methyl (E)-3-(((4-methoxyphenyl)imino)methyl)-1-methyl-2-(1-phenylethyl)-1H-indole-6- carboxylate (3fg) The general procedure (C) was applied to methyl (E)-3-(((4- methoxyphenyl)imino)methyl)-1-methyl-1h-indole-6-carboxylate (1f, 161 mg, 0.50 mmol, 1.0 eq.) and styrene (2g, 62 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 85/15) afforded the title compound (3fg) as a yellow foam (209 mg, 99 %). mp C. 1 H NMR (400 MHz, CDCl 3 ) δ 8.64 (s, 1H), 8.55 (d, J = S32
33 8.4 Hz, 1H), (m, 1H), 7.86 (dd, J = 8.4, 1.5 Hz, 1H), (m, 2H), (m, 3H), (m, 2H), (m, 2H), 5.03 (q, J = 7.4 Hz, 1H), 3.85 (s, 3H), 3.71 (s, 3H), 3.44 (s, 3H), 1.77 (d, J = 7.3 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 167.9, 157.4, 152.4, 151.0, 146.7, 141.5, 137.1, 129.6, (2C), 127.1, 126.8, 124.2, (2C), (2C), 121.8, (2C), 112.1, 111.1, 55.5, 52.0, 34.8, 31.1, IR (thin film): max = 2948, 1707, 1567, 1433, 1236, 783 cm -1. HRMS (ESI): calculated for C 27 H 27 N 2 O 3 [M+ H] + : ; found (E)-3-(((4-Methoxyphenyl)imino)methyl)-1-methyl-2-(1-phenylethyl)-1H-indole-5- carbonitrile (3gg) The general procedure (C) was applied to methyl (E)-3-(((4- methoxyphenyl)imino)methyl)-1-methyl-1h-indole-5-carbonitrile (1g, 144 mg, 0.50 mmol, 1.0 eq.) and styrene (2g, 62 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 85/15) afforded the title compound (3gg) as a yellow oil (162 mg, 82 %). 1 H NMR (400 MHz, CDCl 3 ) δ 9.08 (dd, J = 1.7, 0.7 Hz, 1H), 8.72 (s, 1H), 7.51 (dd, J = 8.5, 1.7 Hz, 1H), (m, 6H), (m, 2H), (m, 2H), 5.10 (q, J = 7.9 Hz, 1H), 3.83 (s, 3H), 3.52 (s, 3H), 1.88 (d, J = 7.4 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 157.7, 151.6, 150.0, 146.1, 141.1, 139.2, (2C), 128.1, (2C), 126.9, 125.8, 125.7, (2C), 120.7, (2C), 112.5, 109.7, 104.6, 55.5, 34.8, 31.2, IR (thin film): max = 2942, 2220, 1614, 1500, 1289, 1106 cm -1. HRMS (ESI): calculated for C 26 H 24 N 3 O [M+ H] + : ; found (E)-1-(5-Fluoro-1-methyl-2-(1-phenylethyl)-1H-indol-3-yl)-N-(4- methoxyphenyl)methanimine (3hg) The general procedure (c) was applied to (E)-1-(5-fluoro-1- methyl-1h-indol-3-yl)-n-(4-methoxyphenyl)methanimine (1h, 141 mg, 0.50 mmol, 1.0 eq.) and styrene (2g, 0.62 mg, 0.6 mmol, 1.2 eq.). Silica gel chromatography (eluent pentane/etoac 90/10) S33
A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Διαβάστε περισσότεραSupporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction
Supporting Information ne-pot Approach to Chiral Chromenes via Enantioselective rganocatalytic Domino xa-michael-aldol Reaction Hao Li, Jian Wang, Timiyin E-Nunu, Liansuo Zu, Wei Jiang, Shaohua Wei, *
Διαβάστε περισσότεραSupporting Information
Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and
Διαβάστε περισσότεραDirect Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3
Supporting Information Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo* Graduate
Διαβάστε περισσότεραCopper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic
Διαβάστε περισσότεραDirect Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines
Direct Palladium-Catalyzed Arylations of Aryl Bromides with 2/9-Substituted Pyrimido[5,4-b]indolizines Min Jiang, Ting Li, Linghua Meng, Chunhao Yang,* Yuyuan Xie*, and Jian Ding State Key Laboratory of
Διαβάστε περισσότεραCopper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation
Διαβάστε περισσότεραSupporting Information
Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,
Διαβάστε περισσότεραSupporting Information for
Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
Διαβάστε περισσότεραEnantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α,
Διαβάστε περισσότεραSupporting Information
Supporting Information Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH 2 CF 3 or ICH 2 CHF 2 Leading to β-cf 3 /CHF 2 -Substituted Ketones Niannian Yi, Hao Zhang, Chonghui Xu, Wei
Διαβάστε περισσότεραSupporting Information. Table of Contents. II. Experimental procedures. II. Copies of 1H and 13C NMR spectra for all compounds
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2017 Laboratoire de Méthodologie et ynthèse de Produit aturels. Université du Québec
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Synthesis of 3-omosubstituted Pyrroles via Palladium- Catalyzed Intermolecular Oxidative Cyclization
Διαβάστε περισσότεραHiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl
Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl Philippe Pierrat, Philippe Gros* and Yves Fort Synthèse Organométallique
Διαβάστε περισσότεραFirst DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of
Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch
Διαβάστε περισσότεραVilsmeier Haack reagent-promoted formyloxylation of α-chloro-narylacetamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Vilsmeier aack reagent-promoted formyloxylation of α-chloro-arylacetamides by formamide Jiann-Jyh
Διαβάστε περισσότεραSupporting Information
Supporting Information Ceric Ammonium Nitrate (CAN) catalyzed efficient one-pot three component aza-diels-alder reactions for a facile synthesis of tetrahydropyranoquinoline derivatives Ravinder Goud Puligoundla
Διαβάστε περισσότεραFluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine
Διαβάστε περισσότεραSupporting Information. Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors
Supporting Information Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors Frédéric Pin, a Frédéric Buron, a Fabienne Saab, a Lionel Colliandre,
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan
Διαβάστε περισσότεραSupplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac
Διαβάστε περισσότεραSupporting Information
Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State
Διαβάστε περισσότεραRh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A. new Entry to N-Carbamate Protected Arylamines
Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A new Entry to N-Carbamate Protected Arylamines Bing Zhou,* Juanjuan Du, Yaxi Yang,* Huijin Feng, Yuanchao Li Shanghai Institute of Materia Medica,
Διαβάστε περισσότεραSupporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic
Supporting Information Asymmetric Binary-acid Catalysis with Chiral Phosphoric Acid and MgF 2 : Catalytic Enantioselective Friedel-Crafts Reactions of β,γ- Unsaturated-α-Ketoesters Jian Lv, Xin Li, Long
Διαβάστε περισσότεραSupporting Information
Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General
Διαβάστε περισσότεραHighly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces
Highly enantioselective cascade synthesis of spiropyrazolones Alex Zea a, Andrea-Nekane R. Alba a, Andrea Mazzanti b, Albert Moyano a and Ramon Rios a,c * Supporting Information NMR spectra and HPLC traces
Διαβάστε περισσότεραEfficient and Simple Zinc mediated Synthesis of 3 Amidoindoles
Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry SUPPRTIG IFRMATI Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Anahit Pews-Davtyan and Matthias Beller* Leibniz-Institut
Διαβάστε περισσότεραDivergent synthesis of various iminocyclitols from D-ribose
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,
Διαβάστε περισσότεραEco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 SUPPRTIG IFRMATI Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst-
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information Copper-catalysed intramolecular O-arylation: a simple
Διαβάστε περισσότεραCopper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds. in Aromatic Amides
Supporting Information for Copper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds in Aromatic Amides Feifan Wang, Qiyan Hu, Chao Shu, Zhiyang Lin, Dewen Min, Tianchao Shi and Wu Zhang* Key Laboratory
Διαβάστε περισσότεραSupporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Proton nuclear magnetic resonance ( 1
Διαβάστε περισσότεραSupporting information
Electronic upplementary Material (EI) for New Journal of Chemistry. This journal is The Royal ociety of Chemistry and the Centre National de la Recherche cientifique 7 upporting information Lipase catalyzed,-addition
Διαβάστε περισσότεραLewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes
Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory
Διαβάστε περισσότεραSUPPORTING INFORMATION. Transition Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts
S1 SUPPORTING INFORMATION Transition Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts Hao Yu, Zhen Li, and Carsten Bolm* Institute of Organic Chemistry, RWTH Aachen University
Διαβάστε περισσότεραSupporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with. β-nitroalkenes. Contents. 1. General Information S2
Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with β-nitroalkenes Jing Zheng, Dahai Wang, and Sunliang Cui* College of Pharmaceutical Sciences, Zhejiang University,
Διαβάστε περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 1 A Facile Way to Synthesize 2H-Chromenes: Reconsideration of the Reaction Mechanism between Salicylic Aldehyde and
Διαβάστε περισσότεραAminofluorination of Fluorinated Alkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Synthesis of ɑ CF 3 and ɑ CF 2 H Amines via Aminofluorination of Fluorinated Alkenes Ling Yang,
Διαβάστε περισσότεραThe Free Internet Journal for Organic Chemistry
The Free Internet Journal for Organic Chemistry Paper Archive for Organic Chemistry Arkivoc 2018, part iii, S1-S6 Synthesis of dihydropyranones and dihydropyrano[2,3- d][1,3]dioxine-diones by cyclization
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Modular Synthesis of Propargylamine Modified Cyclodextrins by a Gold(III)-catalyzed Three Component
Διαβάστε περισσότεραSite-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran
1 Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran Munawar Hussain, a Rasheed Ahmad Khera, a Nguyen Thai Hung, a Peter Langer* a,b a Institut für Chemie, Universität Rostock,
Διαβάστε περισσότεραSupporting Information for Synthesis of Fused N-Heterocycles via Tandem C-H Activation
This journal is The Royal Society of Chemistry 212 Supporting Information for Synthesis of Fused -Heterocycles via Tandem C-H Activation Ge Meng, Hong-Ying iu, Gui-Rong Qu, John S. Fossey, Jian-Ping Li,*
Διαβάστε περισσότεραFacile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang*
Facile construction of the functionalized 4H-chromene via tandem benzylation and cyclization Jinmin Fan and Zhiyong Wang* Hefei National Laboratory for Physical Science at Microscale, Joint- Lab of Green
Διαβάστε περισσότεραSupporting Information For: Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes
Supporting Information For: Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes Xiao-Hui Yang and Vy M. Dong* dongv@uci.edu Department of Chemistry, University
Διαβάστε περισσότεραRegioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.
Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section
Διαβάστε περισσότεραand Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu
Διαβάστε περισσότεραRhodium-Catalyzed Oxidative Decarbonylative Heck-type Coupling of Aromatic Aldehydes with Terminal Alkenes
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Rhodium-Catalyzed Oxidative Decarbonylative Heck-type
Διαβάστε περισσότεραZuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL
Photoredox-Catalyzed Intramolecular Difluoromethylation of -Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H Containing 2- Azaspiro[4.5]deca-6,9-diene-3,8-diones. Zuxiao
Διαβάστε περισσότεραRoom Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled
Supporting Information for: Room Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Stereoselectivity Reversal
Διαβάστε περισσότεραMetal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information for Metal-free Oxidative Coupling of Amines with Sodium Sulfinates:
Διαβάστε περισσότεραSupporting Information
Supporting Information Transition-metal-free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds Qiyi Yao, Lingkai Kong, Mengdan Wang,
Διαβάστε περισσότεραgem-dichloroalkenes for the Construction of 3-Arylchromones
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Pd(OAc)2/S=PPh3 Accelerated Activation of gem-dichloroalkenes for the Construction of 3-Arylchromones
Διαβάστε περισσότεραElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Electronic Supplementary Information (ESI) For Iron-Catalysed xidative Amidation of Alcohols with Amines Silvia Gaspa, a Andrea
Διαβάστε περισσότεραMandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes
1 Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes Gonzalo Blay, Isabel Fernández, Alícia Marco-Aleixandre, and José R. Pedro Departament de Química Orgànica, Facultat de Química,
Διαβάστε περισσότεραSupporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Anhydrous solvents were transferred by
Διαβάστε περισσότεραSupporting Information
Supporting Information Selective Synthesis of xygen-containing Heterocycles via Tandem Reactions of 1,2-Allenic Ketones with Ethyl 4-Chloroacetoacetate Qiang Wang, a, b Zhouqing Xu b and Xuesen Fan a *
Διαβάστε περισσότεραKishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 204 Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng
Διαβάστε περισσότεραExperimental procedure
Supporting Information for Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide Sébastien Alazet 1,2, Kevin Ollivier 1 and Thierry Billard* 1,2 Address: 1 Institute
Διαβάστε περισσότεραSupporting Information for
Supporting Information for Palladium-Catalyzed C-H Bond Functionalization of C6-Arylpurines Hai-Ming Guo,* Wei-Hao Rao, Hong-Ying iu, Li-Li Jiang, Ge ng, Jia-Jia Jin, Xi-ing Yang, and Gui-Rong Qu* College
Διαβάστε περισσότεραSupporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe
Διαβάστε περισσότεραFerric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids using - Dichlorodiphenylmethane
Supporting Information Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids using - Dichlorodiphenylmethane Chang-Hee Lee,, Soo-Min Lee,, Byul-Hana Min, Dong-Su Kim, Chul-Ho
Διαβάστε περισσότεραSynthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions
This journal is The Royal Society of Chemistry 213 Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions Wenjing Cui, a Bao Zhaorigetu,* a Meilin Jia, a and Wulan
Διαβάστε περισσότεραIodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via
Διαβάστε περισσότεραConstruction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol
Supporting Information for: Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol Yu-Fang Zhang, Diao Chen, Wen-Wen
Διαβάστε περισσότεραSupporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds
Supporting Information for Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds Zhongxue Fang, a Yongquan Ning, a Pengbing Mi, a Peiqiu Liao, a Xihe Bi* a,b a Department of Chemistry,
Διαβάστε περισσότεραFree Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2
Free Radical Initiated Coupling Reaction of Alcohols and Alkynes: not C-O but C-C Bond Formation Zhongquan Liu,* Liang Sun, Jianguo Wang, Jie Han, Yankai Zhao, Bo Zhou Institute of Organic Chemistry, Gannan
Διαβάστε περισσότεραOxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br)
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using
Διαβάστε περισσότεραTributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate
upporting Information Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate Jing-Yu Wu, Zhi-Bin Luo, Li-Xin Dai and Xue-Long Hou* a tate Key Laboratory of Organometallic
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Silver or Cerium-Promoted Free Radical Cascade Difunctionalization
Διαβάστε περισσότεραSUPPORTING INFORMATION. 1. General... S1. 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc...
SUPPORTING INFORMATION Table of contents 1. General.... S1 2. General procedure for the synthesis of compounds 3 and 4 in the absence of AgOAc... S2 3. General procedure for the synthesis of compounds
Διαβάστε περισσότεραSupporting Information
S1 Supporting Information Benzannulation from Alkyne without tallic Catalysts at Room Temperature to 100 o C Tienan Jin,* Fan Yang and Yoshinori Yamamoto* Department of Chemistry, Graduate School of Science,
Διαβάστε περισσότεραSupporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process Jincan Zhao 1, Hong Fang 1, Jianlin Han* 1,2 and Yi Pan* 1
Διαβάστε περισσότεραSelective Synthesis of Indoles by Cobalt(III) Catalyzed. C H/N O Functionalization with Nitrones
Supporting Information Selective Synthesis of Indoles by Cobalt(III) Catalyzed C H/N O Functionalization with Nitrones Hui Wang, Marc Moselage, María J. González, and Lutz Ackermann* Institut für Organische
Διαβάστε περισσότεραSupporting Information
Electronic upplementary Material (EI) for Green Chemistry. This journal is The Royal ociety of Chemistry 204 upporting Information ynthesis of sulfonamides via I 2 -mediated reaction of sodium sulfinates
Διαβάστε περισσότεραThe N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information.
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2018 The,-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H Carbonylation using
Διαβάστε περισσότεραSupporting Information. for. Highly Selective Hydroiodation of Alkynes Using. Iodine-Hydrophosphine Binary System
Supporting Information for Highly Selective Hydroiodation of Alkynes Using Iodine-Hydrophosphine Binary System Shin-ichi Kawaguchi and Akiya Ogawa * Department of Applied Chemistry, Graduate School of
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VCH 2014 69451 Weinheim, Germany Copper-Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives** Xiaodong Tang, Liangbin
Διαβάστε περισσότεραSupplementary information
Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary information Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles
Διαβάστε περισσότεραSupporting Information
Supporting Information Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates (ynones, ynamide): Construction of -Pyrones and 3(2H)-Furanones Starting from Identical Materials Feng Wang,
Διαβάστε περισσότεραSupporting Information
S1 Supporting Information Synthesis of 2-Arylated Hydroxytyrosol Derivatives via Suzuki-Myaura Cross-Coupling Roberta Bernini, a Sandro Cacchi, b* Giancarlo Fabrizi, b* Eleonora Filisti b a Dipartimento
Διαβάστε περισσότεραSupporting Information. A catalyst-free multicomponent domino sequence for the. diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-
Supporting Information for A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3- (arylamino)allyl]chromen-4-ones Pitchaimani Prasanna 1, Pethaiah
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Diphenylprolinol Silyl Ether as a Catalyst in an Enantioselective, Catalytic, Formal Aza [3+3] Cycloaddition Reaction for the Formation of
Διαβάστε περισσότεραCopper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols. Support Information
Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols Dr. Xiao un Tang and Prof. Qing un Chen* Key Laboratory of Organofluorine Chemistry,
Διαβάστε περισσότεραEffect of uridine protecting groups on the diastereoselectivity
Supporting Information for Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5 -alkynylation Raja Ben Othman, Mickaël J. Fer, Laurent Le Corre, Sandrine Calvet-Vitale*
Διαβάστε περισσότεραSupporting Information
1 upporting Information Rhodium(III)-Catalyzed rtho Halogenations of N-Acylsulfoximines and ynthetic Applications toward Functionalized ulfoximine Derivatives Ying Cheng, Wanrong Dong, Kanniyappan Parthasarathy,
Διαβάστε περισσότεραSequential catalysis for the production of sterically hindered amines: Ruthenium(II)-catalyzed C-H bond activation and hydrosilylation of imines
Electronic Supporting Information Sequential catalysis for the production of sterically hindered amines: Ruthenium(II)-catalyzed C- bond activation and hydrosilylation of imines Bin Li, Charles B. Bheeter,
Διαβάστε περισσότεραSynthesis and evaluation of novel aza-caged Garcinia xanthones
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Synthesis and evaluation of novel aza-caged Garcinia xanthones Xiaojin Zhang, a,1 Xiang Li, a,1 Haopeng Sun, * b Zhengyu Jiang,
Διαβάστε περισσότεραSupporting Information
Supporting Information Rhodium-catalyzed Intramolecular Dehydrogenative Aryl Aryl Coupling Using Air as Terminal Oxidant Hannah Baars, 1,2 Yuto Unoh, 1 Takeshi Okada, 1 Koji Hirano, 1 Tetsuya Satoh,* 1,3
Διαβάστε περισσότεραSupporting Information
Supporting Information Co(III)-Catalyzed Synthesis of Quinazolines via C-H Activation of -Sulfinylimines and Benzimidates Fen Wang, He Wang, Qiang Wang, Songjie Yu, Xingwei Li* Dalian Institute of Chemical
Διαβάστε περισσότερα9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer
Διαβάστε περισσότεραFirst Total Synthesis of Antimitotic Compound, (+)-Phomopsidin
First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin Takahiro Suzuki, a Kenji Usui, a Yoshiharu Miyake, a Michio Namikoshi, b and Masahisa Nakada a, * a Department of Chemistry, School of Science
Διαβάστε περισσότεραSupporting Information
Supporting Information Metal-Free Direct Intramolecular Carbotrifluoromethylation of Alkenes to Functionalized Trifluoromethyl Azaheterocycles Lei Li, Min Deng, Sheng-Cai Zheng, Ya-Ping Xiong, Li-Jiao
Διαβάστε περισσότεραSupporting Information. Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles
Supporting Information for Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles Angélica de Fátima S. Barreto*, Veronica Alves dos Santos, and Carlos
Διαβάστε περισσότεραBrønsted Acid-Catalyzed Hydroarylation of Activated. Olefins
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 204 Brønsted Acid-Catalyzed Hydroarylation of Activated Olefins Ivana Fleischer* and Jola Pospech
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VC 007 9 Weinheim, Germany ew ear Infrared Dyes and Fluorophores Based on Diketopyrrolopyrroles Dipl.-Chem. Georg M. Fischer, Dipl.-Chem. Andreas P. Ehlers, Prof. Dr. Andreas
Διαβάστε περισσότεραPd Catalyzed Carbonylation for the Construction of Tertiary and
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Pd Catalyzed Carbonylation for the Construction of Tertiary and Quaternary
Διαβάστε περισσότεραRegiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridines by Suzuki and Sonogashira cross-coupling reactions
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 217 Regiocontrolled functionalization of 2,3-dihalogenoimidazo[1,2-a]pyridines
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2018 Palladium-catalyzed direct approach to α-cf 3 aryl ketones from arylboronic acids Bo
Διαβάστε περισσότεραCopper-Catalyzed Oxidative Coupling of Acids with Alkanes Involving Dehydrogenation: Facile Access to Allylic Esters and Alkylalkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary information Copper-Catalyzed xidative Coupling of Acids with Alkanes Involving Dehydrogenation:
Διαβάστε περισσότεραmulticomponent synthesis of 5-amino-4-
Supporting Informartion for Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4- (arylselanyl)-1h-pyrazoles Camila S. Pires 1, Daniela H. de Oliveira 1, Maria R. B. Pontel 1, Jean
Διαβάστε περισσότερα