Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids using - Dichlorodiphenylmethane
|
|
|
- Ξανθίππη Παπακωνσταντίνου
- 5 χρόνια πριν
- Προβολές:
Transcript
1 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 Jun* Department of Chemistry, Yonsei University, 50 Yonsei-ro, Seodaemun-gu, Seoul 03722, Republic of Korea New Drug Development Center, Daegu-Gyeongbuk Medical Innovation Foundation, Daegu 41061, Republic of Korea * junch@yonsei.ac.kr Table of Contents 1. General.. S2 2. Materials S2 3. Experimental S2 4. Compounds characterization data S H and 13 C NMR spectra S10 6. Mechanistic investigation of bromination of alcohol S45 7. Chiral GC data of the chlorination reaction product S46 8. References S46 S1
2 1. General Flash column chromatography was performed using mesh silica gel and was monitored by using analytical thin-layer chromatography (TLC) on silica gel plates using UV light as a visualizing agent, p-anisaldehyde and KMnO 4 solution as the staining solutions, and heat as developing agent. Gas chromatographic analyses were performed using an Agilent 7890A instrument with FID detector and an Agilent HP-5 capillary column. Mass chromatography analyses were performed using a HP- 5MS column. Chiral gas chromatographic analyses were performed using a Donam Instruments INC. DS 6200 instrument with an FID detector and an RtRbDEXcst column. 1 H NMR (400 MHz) and 13 C NMR (100 MHz) data was collected with reported chemical shifts being relative to residual deuteriated solvent peaks (for 1 H NMR spectra deuteriated solvent peaks for CDCl 3 (for 1 H, δ = 7.26), DMSO (for 1 H, δ = 2.50). Chemical shifts are reported in ppm and multiplicities as s = singlet, d = doublet, t = triplet, q = quartet, quint = quintet, m = multiplet. 13 C NMR spectra peaks are referenced to CDCl 3 (for 13 C, δ = 77.26), DMSO (for 13 C, δ 39.5) as internal standard. 2. Materials Commercially available, reagent grade chemicals 1a-q, 2b-d, 3b-f, 5a-b, 10a-j were used as received unless otherwise stated. Ferric chloride (3a) and α,α-dichlorodiphenylmethane 1 (2a) were purchased from Sigma Aldrich and Alfa Aesar. 3. Experimental - Example procedure for preparation of (1-chloroethyl)benzene (4a) (Table 1) To a 1 ml pressure vial were added 1-phenylethanol (1a, 24.1 μl, 0.2 mmol), dichlorodiphenylmethane (2a, 46.2 μl, 0.24 mmol), ferric trichloride (3a, mg, mmol) and chloroform (0.1 ml). The mixture was stirred at room temperature for 1 h, diluted with chloroform, and filtered through a silica column. The yield of (1-chloroethyl)benzene (4a, 99%) was determined by using GC-MS analysis with hexadecane as the internal standard. - Example procedure for preparation of (bromomethyl)benzene (4m) and S2
3 (iodomethyl)benzene (4n) (Table 3) To a 1 ml pressure vial were added benzyl alcohol (1b, 24.1 μl, 0.2 mmol), dichlorodiphenylmethane (2a, 46.2 μl, 0.24 mmol), ferric trichloride (3a, mg, mmol), Lithium halide (LiBr (5a), LiI (5b), 0.8 mmol) and chloroform (0.1 ml). The mixture was stirred at room temperature for 1 h, diluted with chloroform, and filtered through a silica column. The yields of (bromomethyl)benzene (4m, 98%) and (iodomethyl)benzene (4n, 97%) were determined by using GC-MS analysis with hexadecane as the internal standard. - Example procedure for preparation of N-benzylbenzamide (13a) (Table 5) To a 1 ml pressure vial were added benzoic acid (10a, mg, 2.0 mmol), dichlorodiphenylmethane (2a, μl, 2.4 mmol), ferric trichloride (3a, 16.2 mg, 0.1 mmol) and chloroform (1.0 ml). The mixture was stirred at room temperature for 1 h, and a mixture of triethylamine (558.0 μl, 4.0 mmol) and benzyl amine (14a, μl, 3.0 mmol) were then added. The mixture was diluted with dichloromethane, dried over anhydrous MgSO 4 and filtered through Celite. The concentrated filtrate was subjected to column chromatography on silica gel using 10% EtOAc in hexane to give N-benzylbenzamide (13a, mg, 92%) as a white solid. S3
4 4. Compounds characterization data (1-chloroethyl)benzene (4a) [CAS No ]; Obtained as a colorless liquid (99% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), 5.12 (q, J = 6.8 Hz, 1H) 1.87 (dd, J = 6.8 Hz, J = 0.8 Hz,3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.0, 128.9, 128.5, 126.7, 59.0, (chloromethyl)benzene (4b) [CAS No ]; Obtained as a colorless liquid (99% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), 4.61 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 137.7, 129.0, 128.8, 128.6, (chloromethyl)-4-methylbenzene (4c) [CAS No ]; Obtained as a colorless liquid (99% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ 7.44 (d, J = 8.0 Hz, 2H), 7.33 (d, J = 7.9 Hz, 2H), 4.72 (s, 2H), 2.52 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 138.2, 135.1, 129.9, 129.1, 46.8, (chloromethyl)-4-(trifluoromethyl)benzene (4d) [CAS No ]; Obtained as a colorless liquid (90% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ 7.63 (d, J = 8.1 Hz, 2H), 7.52 (d, J = 8.1 Hz, 2H), 4.62 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 141.2, (q, J = 31.9 Hz), 129.4, (q, J = 3.8 Hz), (q, J = Hz), chloro-4-(chloromethyl)benzene (4e) [CAS No ]; Obtained as a colorless liquid (93% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ 7.33 (d, J = 1.6 Hz, 4H), 4.55 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 136.1, 134.5, 130.1, 129.1, chloromethylfuran (4g) [CAS No ]; Obtained as a colorless liquid (65% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 2H), 4.60 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 150.2, 143.7, 111.0, 110.0, S4
5 2-(chloromethyl)thiophene (4h) [CAS No ]; Obtained as a colorless liquid (53% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ 7.34 (dd, J 1 = 1.5 Hz, J 2 = 6.8 Hz, 1H), 7.12 (d, J = 4.5 Hz, 1H), 7.00 (dd, J 1 = 4.7 Hz, J 2 = 6.8 Hz, 1H), 4.84 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 140.0, 127.6, (2C), (2-chloroethyl)benzene (4i) [CAS No ]; Obtained as a colorless liquid (92% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), 3.78 (t, J = 7.4 Hz, 2H), 3.14 (t, J = 7.48 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 138.3, 129.0, 128.9, 128.7, 127.0, 45.1, (2-chloropropyl)benzene (4j) [CAS No ]; Obtained as a colorless liquid (78% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), (m, 1H), 3.04 (spilitted AB quartet, J = 13.8 Hz, J = 7.0 Hz, 2H), 1.52 (d, J = 6.5 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 138.2, 129.6, 128.6, 127.0, 58.8, 46.9, (2-chloro-2-methylpropyl)benzene (4k) [CAS No ]; Obtained as a colorless liquid (94% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), 3.09 (s, 2H), 1.59 (s, 6H); 13 C NMR (100 MHz, CDCl 3 ) δ 137.2, 131.0, 128.2, 127.1, 70.3, 52.0, chlorooctane (4l) [CAS No ]; Obtained as a colorless liquid (86% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ 3.54 (t, J = 6.8 Hz, 2H), (m, 2H), (m, 2H), (m, 8H), 0.88 (t, J = 6.8 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 45.4, 32.9, 32.0, 29.4, 29.1, 27.1, 22.9, Chloro-2-pentanone (4m) [CAS No ]; Obtained as a colorless liquid (69% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), 2.61 (t, J = 18.8 Hz, 2H), 2.16 (s, 3H), 2.01 (t, J = 17.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 207.8, 44.6, 40.4, 30.3, S5
6 4-(chloromethyl)cyclohex-1-ene (4n) [CAS No ]; Obtained as a colorless liquid (71% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), 3.47 (d, J = 8.4 Hz, 2H), (m, 1H), (m, 2H), (m, 1H), (m, 2H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 127.2, 125.6, 50.4, 36.4, 29.5, 26.5, (bromomethyl)benzene (4o) [CAS No ]; Obtained as a colorless liquid (98% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 3H), 4.53 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 138.0, 129.2, 129.0, 128.5, (iodomethyl)benzene (4p) [CAS No ]; Obtained as a colorless liquid (97% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 3H), 4.49 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 139.4, 129.0, 128.9, 128.0, bromooctane (4q) [CAS No ]; Obtained as a colorless liquid (85% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ 3.37 (t, J = 18.4 Hz, 2H), (m, 2H), (m, 2H), (m, 8H), 0.86 (t, J = 18.0 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 34.2, 33.1, 32.0, 29.3, 29.0, 28.4, 22.9, iodooctane (4r) [CAS No ]; Obtained as a colorless liquid (79% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ 3.15 (t, J = 18.8 Hz, 2H), (m, 2H), (m, 10H), 0.86 (t, J = 17.6 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 33.8, 32.0, 30.7, 29.3, 28.7, 22.8, 14.3, chlorooctane (rac-4s) [CAS No ]; Obtained as a colorless liquid (27.8 mg, 94%); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 2H), 1.50 (d, J = 6.5 Hz, 3H), (m, 2H), (m, 6H), 0.89 (t, J = 6.7 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 59.2, 40.6, 32.0, 29.0, 26.9, 25.6, 22.8, (chloromethyl)benzoic acid (4t) [CAS No ]; Obtained as a white solid (299.2 mg, 88%); 1 H NMR (400 MHz, DMSO) δ 13.0 (s, 1H), 7.95 (d, J = S6
7 8.2 Hz, 2H), 7.54 (d, J = 8.2 Hz, 2H), 4.81 (s, 2H); 13 C NMR (100 MHz, DMSO) δ 167.0, 142.4, 130.7, 129.7, 128.9, Benzoyl chloride (11a) [CAS No ]; Obtained as a colorless liquid (95% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 1H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 168.7, 135.6, 133.4, 131.7, methylbenzoyl chloride (11b) [CAS No ]; Obtained as a colorless liquid (92% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 2H), 2.44 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 168.2, 147.0, 131.7, 130.6, 129.8, 22,0. 4-fluorobenzoyl chloride (11c) [CAS No ]; Obtained as a colorless liquid (78% in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 168.6, (d, J = 520 Hz), (d, J = 40 Hz), (d, J = 40 Hz), (d, J = 80 Hz). 4-(trifluoromethyl)benzoyl chloride (11d) [CAS No ]; Obtained as a colorless liquid (57 % in GC yield with hexadecane as the internal standard); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 167.9, 136.8, 136.5, 136.4, 131.8, (q, J = 14 Hz), 124.8, N-benzylbenzamide (13a) [CAS No ]; Obtained as a white solid (388.4 mg, 92%); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 8H), 6.47 (s, 1H), 4.65 (d, J = 5.7 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 167.6, 138.4, 134.6, 131.8, 129.0, 128.8, 128.2, 127.9, 127.2, N-benzyl-4-methylbenzamide (13b) [CAS No ]; Obtained as a white solid (360.2 mg, 80%); 1 H NMR (400 MHz, CDCl 3 ) δ 7.70 (d, J = 8.0 Hz, 2H), (m, 5H), 7.72 (d, J = 7.8 Hz, 2H), 6.62 (s, 1H), 4.60 (d, J = 5.5 Hz, 2H), 2.39 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 167.5, 142.1, 138.6, 131.7, 129.4, 128.9, S7
8 128.0, 127.7, 127.2, 44.2, N-benzyl-4-fluorobenzamide (13c) [CAS No ]; Obtained as a white solid (330.0 mg, 72%); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 1H), (m, 2H), (m, 4H), (m, 1H), (m, 2H), 6.45 (s, 1H), 4.63 (d, J = 5.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 166.6, 138.2, 129.6, 129.5, 129.1, 128.2, 127.9, 116.0, 115.8, N-benzyl-4-(trifluoromethyl)benzamide (13d) [CAS No ]; Obtained as a white solid (295.8 mg, 53%); 1 H NMR (400 MHz, CDCl 3 ) δ 7.89 (d, J = 8.1 Hz, 2H), 7.68 (d, J = 8.2 Hz, 2H), (m, 5H), 6.52 (s, 1H), 4.65 (d, J = 5.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 166.7, 138.3, 138.2, (q, J = 32.4 Hz), 129.4, 128.4, 128.3, 128.0, (q, J = 3.4 Hz), (q, J = Hz), 44.8 N-benzyl-4-cyanobenzamide (13e) [CAS No ]; Obtained as a white solid (264.4 mg, 56%); 1 H NMR (400 MHz, CDCl 3 ) δ 7.88 (d, J = 1.7 Hz, 2H), 7.86 (d, J = 1.8 Hz, 2H), (m, 5H), 6.62 (s, 1H), 4.63 (d, J = 5.6 Hz, 2); 13 C NMR (100 MHz, CDCl 3 ) δ 165.8, 138.4, 137.8, 132.6, 128.9, 128.5, 128.2, 127.9, 118.2, 115.2, N-benzyl-2-naphthamide (13f) [CAS No ]; Obtained as a white solid (433.5 mg, 83%); 1 H NMR (400 MHz, CDCl 3 ) δ 8.31 (s, 1H), (m, 4H), (m, 2H) (m, 5H), 6.63 (s, 1H), 4.71 (d, J = 5.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 167.7, 138.4, 135.0, 132.8, 131.8, 129.1, 129.0, 128.7, 128.2, 128.0, 127.9, 127.7, 127.0, 123.8, N-benzylcyclohexanecarboxamide (13g) [CAS No ]; Obtained as a white solid (373.5 mg, 86%); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), 5.73 (s, 1H), 4.43 (d, J = 5.7 Hz, 2H), (m, 1H), 1.91 (d, J = 1.8 Hz, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 3H) ; 13 C NMR (100 MHz, CDCl 3 ) δ 176.4, 139.1, 129.3, 128.3, 128.0, 46.1, 44.0, 30.3, N-benzyloctanamide (13h) [CAS No ]; Obtained as a white solid S8
9 (265.8 mg, 57%); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), 5.71 (s, 1H), 4.44 (d, J = 5.7 Hz, 2H), 2.21 (t, J = 7.4 Hz, 2H), 1.65 (quint, J = 14.8 Hz, J = 7.0 Hz, 2H), (m, 8H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 173.5, 139.0, 1283, 1284, 128.1, 44.1, 37.4, 32.2, 29.8, 29.6, 26.3, 23.1, N-benzyl-2-methylheptanamide (13i) [CAS No ]; Obtained as a white solid (346.3 mg, 79%); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), 5.73 (s, 1H), 4.45 (dd, J = 5.6 Hz, J = 1.4 Hz, 2H), (m, 1H), (m, 1H), (m, 1H), (m, 4H), 1.16(d, J = 6.8 Hz, 3H), 0.88 (t, J = 6.7 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 176.4, 138.5, 128.6, 127.7, 127.4, 43.4, 41.6, 34.0, 29.6, 22.6, 17.8, N-benzylpivalamide (13j) [CAS No ]; Obtained as a white solid (259.9 mg, 68%); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 5H), 5.94 (s, 1H), 4.43 (d, J = 5.6 Hz, 2H), 1.22 (s, 9H); 13 C NMR (100 MHz, CDCl 3 ) δ 178.5, 138.9, 128.9, 127.8, 127.6, 43.8, 38.9, N-cyclohexylbenzamide (13k) [CAS No ]; Obtained as a white solid (349.4 mg, 86%); 1 H NMR (400 MHz, CDCl 3 ) δ 7.76 (d, J = 1.1 Hz, 2H), (m, 3H), 5.99 (s, 1H), (m, 1H), (m, 2H), (m, 2H), (m, 1H), (m, 2H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 166.8, 135.3, 131.4, 128.7, 127.1, 48.9, 33.4, 25.8, Heptyl benzoate (13l) [CAS No ]; Obtained as a colorless liquid (352.2 mg, 80%); 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), 7.55 (tt, J = 7.4 Hz, J = 1.9 Hz, 1H), 7.44 (t, J = 7.8 Hz, 2H), 4.32 (t, J = 6.7 Hz, 2H), (m, 2H), (m, 8H), 0.89 (t, J = 6.8 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 166.9, 133.0, 130.7, 129.8, 128.5, 65.4, 32.0, 29.2, 29.0, 26.2, 22.8, S9
10 5. 1 H and 13 C NMR Spectra S10
11 S11
12 S12
13 S13
14 S14
15 S15
16 S16
17 S17
18 S18
19 S19
20 S20
21 S21
22 S22
23 S23
24 S24
25 S25
26 S26
27 S27
28 S28
29 S29
30 S30
31 S31
32 S32
33 S33
34 S34
35 S35
36 S36
37 S37
38 S38
39 S39
40 S40
41 S41
42 S42
43 S43
44 S44
45 6. Mechanistic investigation of bromination of alcohol - Preparation of a,a-dibromodiphenylmethane (Scheme 1) To a 1 ml pressure vial were added dichlorodiphenylmethane (2a, 38.5 μl, 0.2 mmol), ferric trichloride (3a, mg, mmol), lithium bromide (5a, 69.5 mg, 0.8 mmol) and CDCl 3 (0.1 ml). The mixture was stirred at room temperature for 2 h. After 2 h, the mixture was filtered through a silica column. - Preparation of (bromomethyl)benzene (4o) (Scheme 1) To a 1 ml pressure vial were added dichlorodiphenylmethane (2a, 46.2 μl, 0.24 mmol), ferric trichloride (3a, mg, mmol), lithium bromide (5a, 69.5 mg, 0.8 mmol) and chloroform (0.1 ml). The mixture was stirred at room temperature for 2 h and benzyl alcohol (1b, 24.1 μl, 0.2 mmol) was then added. The mixture was diluted with dichloromethane, dried over anhydrous MgSO 4 S45
46 and filtered through a silica column. The yields of (bromomethyl)benzene (4o, 98%) was determined by using GC-MS analysis with hexadecane as the internal standard. 1 H NMR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 3H), 4.53 (s, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 138.0, 129.2, 129.0, 128.5, Chiral GC data of the chlorination reaction product (Scheme 2) entry reaction scheme ee (%) GC data (retention time) Reference (1) (a) Newman, M. S.; Sujeeth, P. K. J. Org. Chem. 1978, 43, (b) Spaggiari, A.; Vaccari, D.; Davoli, P.; Torre, G.; Prati, F. J. Org. Chem. 2007, 72, S46
Supporting 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, *
Direct 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
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
Copper-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
Supporting 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,
Supporting 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
Supporting 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
Vilsmeier 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
Highly 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
Supporting 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
Supporting 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
and 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
Copper-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
Direct 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](/thumbs/87/95187440.jpg "Direct 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
Regioselectivity 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
Supporting 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
Fluorinative 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
Supporting 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
Hiyama 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
Supporting 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
Aminofluorination 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,
Supporting 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
Supporting 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
Supporting 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,*
First 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
Supporting 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
Supporting 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
Supporting 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
Oxyhalogenation 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
Rh(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,
Supporting 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
ESI for. A simple and efficient protocol for the palladium-catalyzed. ligand-free Suzuki reaction at room temperature in aqueous DMF.
ESI for A simple and efficient protocol for the palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF Chun Liu,* Qijian i, Fanying Bao and Jieshan Qiu State Key Laboratory
Eco-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-
Synthesis 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
Electronic 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
Supporting 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,
Copper-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,
Mandelamide-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,
The 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
Lewis 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
Kishore 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
Supporting 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
Efficient 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
Phosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions
Supplementary Information for Phosphorus xychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions u Chen,* a,b Xunfu Xu, a Liu Liu, a Guo Tang,* a
Supporting 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
Tributylphosphine-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
Site-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,
Electronic Supplementary Information
Electronic Supplementary Information NbCl 3 -catalyzed [2+2+2] intermolecular cycloaddition of alkynes and alkenes to 1,3-cyclohexadiene derivatives Yasushi Obora,* Keisuke Takeshita and Yasutaka Ishii*
Supporting 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
Supporting Information
Supporting Information Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors Tomonari Tanaka,* 1
Rhodium-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
Metal-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:
Divergent 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,
Enantioselective 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,
Cu-Catalyzed/Mediated Synthesis of N-Fluoroalkylanilines from Arylboronic Acids: Fluorine Effect on the Reactivity of Fluoroalkylamines
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 S1 Cu-Catalyzed/Mediated Synthesis of N-Fluoroalkylanilines from Arylboronic
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information 1. General experimental methods (S2). 2. Table 1: Initial studies (S2-S4).
Electronic 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
Supporting 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
9-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
Free 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
Supporting 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
Supporting 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
Fast copper-, ligand- and solvent-free Sonogashira coupling in a ball mill
Electronic Supporting Information Fast copper-, ligand- and solvent-free Sonogashira coupling in a ball mill Rico Thorwirth, Achim Stolle * and Bernd ndruschka Institute for Technical Chemistry and Environmental
Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent
Supplementary information for the paper Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent Yang Xue, Ling-Po Li, Yan-Hong He * & Zhi Guan * School of Chemistry and Chemical Engineering,
First 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
multicomponent 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
Supplementary Material
Supplementary Material Control experiments S2 Characterization data for the products S2-S7 References S8 MR spectra for the products S9-S28 S1 Control experiments 2a (99.5 mg, 0.5 mmol), I 2 (50.8 mg,
Pd 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
Room 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
Sotto, 8; Perugia, Italia. Fax: ; Tel: ;
ELECTRONIC SUPPORTING INFORMATION Ermal Ismalaj a, Giacomo Strappaveccia a, Eleonora Ballerini a, Fausto Elisei a, Oriana Piermatti a, Dmitri Gelman b, Luigi Vaccaro a a CEMIN - Dipartimento di Chi mica,
SUPPORTING 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
Supporting 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
Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde. hydrazones leading to N,N -diacylhydrazines and 1,3,4-oxadiazoles
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde hydrazones leading
Supporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Facile diverted synthesis of pyrrolidinyl triazoles
SUPPORTING INFORMATION
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 SUPPORTIG IFORMATIO Visible light-mediated decarboxylative amination of indoline-2- carboxylic
Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of novel 1,2,3-triazolyl derivatives of
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information
![Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information](/thumbs/64/50937700.jpg "Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information")
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans Liang Yun, Shi Tang, Xu-Dong Zhang, Li-Qiu Mao, Ye-Xiang Xie and Jin-Heng Li* Key Laboratory
Supporting 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
Supporting 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 *
Supporting 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
Supplementary 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
Natural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea
Supporting Information Nicrophorusamides A and B, Antibacterial Chlorinated Cyclic Peptides from a Gut Bacterium of the Carrion Beetle Nicrophorus concolor Yern-Hyerk Shin, Suhyun Bae, Jaehoon Sim,,ǁ Joonseong
Sequential 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,
Supporting 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
Supplement: Intramolecular N to N acyl migration in conformationally mobile 1 -acyl-1- systems promoted by debenzylation conditions (HCOONH 4
Cent. Eur. J. Chem. 9(5) 2011 S164-S175 DI: 10.2478/s11532-011-0082-y Central European Journal of Chemistry Supplement: Intramolecular to acyl migration in conformationally mobile 1 -acyl-1- benzyl-3,4
Supporting 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
gem-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
Supporting 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
Supporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of Multi-Substituted Vinylsilanes via Copper(I)-Catalyzed Hydrosilylation
Facile 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
Supporting 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,
Cu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates
Cu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates Yoshihiko Yamamoto,* Naohiro Kirai and Yu arada Department of Applied Chemistry, Graduate School of Science and Engineering,
Supporting Information. Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors
Supporting Information Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors Xiao-Peng He, abd Cui Li, d Xiao-Ping Jin, b Zhuo Song, b Hai-Lin Zhang,
Practical Pd(II)-catalyzed C H Alkylation with Epoxides: One-step Syntheses of 3,4-Dihydroisocoumarins
Practical Pd(II)-catalyzed C H Alkylation with Epoxides: One-step Syntheses of 3,4-Dihydroisocoumarins Guolin Cheng, Tuan-Jie Li, and Jin-Quan Yu* Department of Chemistry, The Scripps Research Institute,
Supporting 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,
Palladium-Catalyzed C H Monoalkoxylation of α,β-unsaturated Carbonyl Compounds
Supporting Information Palladium-Catalyzed C H Monoalkoxylation of α,β-unsaturated Carbonyl Compounds Yasunari Monguchi,* Kouki Kunishima, Tomohiro Hattori, Tohru Takahashi, Yuko Shishido, Yoshinari Sawama,
Selective mono reduction of bisphosphine
Griffith Research Online https://research-repository.griffith.edu.au Selective mono reduction of bisphosphine oxides under mild conditions Author etersson, Maria, Loughlin, Wendy, Jenkins, Ian ublished
Eur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 ISSN X SUPPORTING INFORMATION
Eur. J. rg. Chem. 2006 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 ISSN 1434 193X SUPPRTING INFRMATIN Title: ne-pot Synthesis of xo Acid Derivatives by Rh I -Catalyzed Chelation-Assisted Hydroacylation
The 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
Copper-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: