A straightforward metal-free synthesis of 2-substituted thiazolines in air
|
|
- Σωτηρία Μακρή
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information for A straightforward metal-free synthesis of 2-substituted thiazolines in air Michael Trose, Faïma Lazreg, Mathieu Lesieur and Catherine S. J. Cazin* School of Chemistry University of St Andrews, St Andrews, KY16 9ST, United Kingdom Fax: (+) 44 (0) ; cc111@st-andrews.ac.uk S1
2 Table of Contents 1 General considerations... S5 2 Optimisation of reaction conditions... S5 3 In Situ FTIR Spectroscopy... S7 IR spectra of benzonitrile, 1a... S7 IR spectra of 2-Phenyl-4,5-dihydrothiazole, 4a... S7 Reaction between benzonitrile and cysteamine hydrochloride without base... S8 Reaction between benzonitrile and cysteamine hydrochloride in the presence of NaOH... S10 4 Synthesis and characterisation of thiazolines... S11 2-Phenyl-4,5-dihydrothiazole, 4a... S11 2-(4-Fluorophenyl)-4,5-dihydrothiazole, 4b... S11 2-(4-Chlorophenyl)-4,5-dihydrothiazole, 4c... S12 2-(4-Bromophenyl)-4,5-dihydrothiazole, 4d... S12 2-p-Tolyl-4,5-dihydrothiazole, 4e... S12 2-(4-Methoxyphenyl)-4,5-dihydrothiazole, 4f... S13 4-(4,5-Dihydrothiazol-2-yl)aniline, 4g... S13 2-(3-Bromophenyl)-4,5-dihydrothiazole, 4h... S13 2-m-Tolyl-4,5-dihydrothiazole, 4i... S14 3-(4,5-Dihydrothiazol-2-yl)aniline, 4j... S14 2-(3,5-Difluorophenyl)-4,5-dihydrothiazole, 4k... S14 2-(2-Chlorophenyl)-4,5-dihydrothiazole, 4l... S15 2-(2-Bromophenyl)-4,5-dihydrothiazole, 4m... S15 2-(4,5-Dihydrothiazol-2-yl)aniline, 4n... S15 2-(4-Chlorobenzyl)-4,5-dihydrothiazole, 4o... S16 2-Benzyl-4,5-dihydrothiazole, 4p... S16 2-(2-Bromobenzyl)-4,5-dihydrothiazole, 4q... S16 2-(Pyridin-2-yl)-4,5-dihydrothiazole, 4r... S16 2-(Pyridin-3-yl)-4,5-dihydrothiazole, 4s... S17 2-(Pyridin-4-yl)-4,5-dihydrothiazole, 4t... S17 2-(1H-Pyrrol-2-yl)-4,5-dihydrothiazole, 4u... S17 2-(2-Furanyl)-4,5-dihydrothiazole, 4v... S18 2-(Pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w... S18 2-Pentyl-4,5-dihydrothiazole, 4x... S18 2-Cyclohexyl-4,5-dihydrothiazole, 4y... S19 5 NMR spectra... S20 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-phenyl-4,5-dihydrothiazole, 4a... S20 13 C-{ 1 H} NMR (125.7 MHz, CDCl 3, 298K) of 2-phenyl-4,5-dihydrothiazole, 4a... S20 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b... S21 S2
3 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b... S21 19 F-{ 1 H} NMR (376 MHz, 298K) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b... S22 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-chlorophenyl)-4,5-dihydrothiazole, 4c... S23 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4-chlorophenyl)-4,5-dihydrothiazole, 4c... S23 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(4-bromophenyl)-4,5-dihydrothiazole, 4d... S24 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4-bromophenyl)-4,5-dihydrothiazole, 4d... S24 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-p-tolyl-4,5-dihydrothiazole, 4e... S25 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-p-tolyl-4,5-dihydrothiazole, 4e... S25 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-(4-methoxyphenyl)-4,5-dihydrothiazole, 4f... S26 13 C-{ 1 H} NMR (125.7 MHz, CDCl 3, 298K) of 2-(4-methoxyphenyl)-4,5-dihydrothiazole, 4f... S26 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 4-(4,5-dihydrothiazol-2-yl)aniline, 4g... S27 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 4-(4,5-dihydrothiazol-2-yl)aniline, 4g... S27 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(3-bromophenyl)-4,5-dihydrothiazole, 4h... S28 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(3-bromophenyl)-4,5-dihydrothiazole, 4h... S28 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-m-tolyl-4,5-dihydrothiazole, 4i... S29 13 C-{ 1 H} NMR (125.7 MHz, CDCl 3, 298K) of 2-m-tolyl-4,5-dihydrothiazole, 4i... S29 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 3-(4,5-dihydrothiazol-2-yl)aniline, 4j... S30 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 3-(4,5-dihydrothiazol-2-yl)aniline, 4j... S30 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k... S31 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k... S31 19 F-{ 1 H} NMR (376 MHz, 298K) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k... S32 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-(2-chlorophenyl)-4,5-dihydrothiazole, 4l... S33 13 C-{ 1 H} NMR (125.7 MHz, CDCl 3, 298K) of 2-(2-chlorophenyl)-4,5-dihydrothiazole, 4l... S33 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(2-bromophenyl)-4,5-dihydrothiazole, 4m... S34 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(2-bromophenyl)-4,5-dihydrothiazole, 4m... S34 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(4,5-dihydrothiazol-2-yl)aniline, 4n... S35 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4,5-dihydrothiazol-2-yl)aniline, 4n... S35 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(4-chlorobenzyl)-4,5-dihydrothiazole, 4o... S36 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(4-chlorobenzyl)-4,5-dihydrothiazole, 4o... S36 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-benzyl-4,5-dihydrothiazole, 4p... S37 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-benzyl-4,5-dihydrothiazole, 4p... S37 1 H NMR (500 MHz, CDCl 3, 298K, TMS) of 2-(2-bromobenzyl)-4,5-dihydrothiazole, 4q... S38 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(2-bromobenzyl)-4,5-dihydrothiazole, 4q... S38 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(pyridin-2-yl)-4,5-dihydrothiazole, 4r... S39 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(pyridin-2-yl)-4,5-dihydrothiazole, 4r... S39 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(pyridin-3-yl)-4,5-dihydrothiazole, 4s... S40 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(pyridin-3-yl)-4,5-dihydrothiazole, 4s... S40 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(pyridin-4-yl)-4,5-dihydrothiazole, 4t... S41 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(pyridin-4-yl)-4,5-dihydrothiazole, 4t... S41 S3
4 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(1H-pyrrol-2-yl)-4,5-dihydrothiazole, 4u... S42 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(1H-pyrrol-2-yl)-4,5-dihydrothiazole, 4u... S42 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(2-furanyl)-4,5-dihydrothiazole, 4v... S43 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(2-furanyl)-4,5-dihydrothiazole, 4v... S43 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-(pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w... S44 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-(pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w... S44 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-pentyl-4,5-dihydrothiazole, 4x... S45 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-pentyl-4,5-dihydrothiazole, 4x... S45 1 H NMR (400 MHz, CDCl 3, 298K, TMS) of 2-cyclohexyl-4,5-dihydrothiazole, 4y... S46 13 C-{ 1 H} NMR (75 MHz, CDCl 3, 298K) of 2-cyclohexyl-4,5-dihydrothiazole, 4y... S46 6 References... S47 S4
5 1 General considerations All reactions were carried out in air. All reagents were purchased and used as received. 1 H, 13 C-{ 1 H} and 19 F-{ 1 H} Nuclear Magnetic Resonance (NMR) spectra were recorded at 298K on a Brucker Avance 400 Ultrashield or on a Brucker Avance 500 Ultrashield spectrometer using the residual solvent peak for 13 C-{ 1 H} NMR (CDCl 3: δ C = ppm) and TMS as reference for 1 H NMR. Gas chromatography (GC) analyses were performed on an Agilent 7890A apparatus equipped with a flame ionization detector and a (5%-phenyl)-methylpolysiloxane column (30 m, 320 μm, film: 0.25 μm). IR measurements were performed on a ReactIR A15 system (Mettler Toledo Autochem) with a DiComp AgX FiberConduit probe (9.5 mm). Mass spectroscopy was performed by the EPSRC National Mass Spectrometry Service Centre at Swansea University, UK. 2 Optimisation of reaction conditions Table S1. Optimisation of reaction conditions N NH HS 3 1a 3 Cl Base 80 C, 16 h N S 4a Entry 3 (mmol) Base (Loading) Time (h) Conversion (%) 1 1 NaOH (30 mol%) 16 > NaOH (20 mol%) 16 > NaOH (10 mol%) 16 > CsOH (10 mol%) 16 > KOH (10 mol%) 16 > NaOH (5 mol%) NaOH (20 mol%) 16 > NaOH (20 mol%) 2 > 99 (98) c NaOH (20 mol%) 1 94 a Reaction conditions: 1 (0.5 mmol), 3 ( mmol), base-catalyst, 80 ºC, 1-16h. b Conversion determined by GC, based on benzonitrile, average of 2 reactions. c Isolated yield. S5
6 Table S2. Comparison of sources of NaOH a N NH HS 3 1a 3 Cl NaOH 20 mol% 80 C, 2 h N S 4a Entry Base Conversion b (%) 1 NaOH batch1 > 99 2 NaOH batch2 > 99 3 NaOH batch3 > 99 4 NaOH semiconductor grade > 99 a Reaction conditions: 1 (0.5 mmol), 3 (0.75 mmol), NaOH (20 mol%), 80 ºC, 2h. b Conversion determined by GC, based on benzonitrile, average of 2 reactions. S6
7 3 In Situ FTIR Spectroscopy Figure S1 IR spectra of benzonitrile, 1a Figure S2 IR spectra of 2-Phenyl-4,5-dihydrothiazole, 4a S7
8 Reaction between benzonitrile and cysteamine hydrochloride without base PROCEDURE: In air, a 5 ml round bottom flask was charged with benzonitrile (19.4 mmol, 2.0 g) and cysteamine hydrochloride (29.1 mmol, 3.3 g). The mixture was heated at 80 C until cysteamine hydrochloride was completely melted. The probe was submerged in the reaction mixture and the IR measurements were started. The reaction was stirred (350 rpm) at 80 C for 1h under solvent-free conditions. Figure S3 3D plot of in situ IR measurements of the reaction between 1a and 3 without base. S8
9 Figure S4 IR plot of the reaction between 1a and 3 without base. S9
10 Reaction between benzonitrile and cysteamine hydrochloride in the presence of NaOH PROCEDURE: In air, a 5 ml round bottom flask was charged with benzonitrile (19.4 mmol, 2.0 g) and cysteamine hydrochloride (29.1 mmol, 3.3 g). The mixture was heated at 80 C until cysteamine hydrochloride was completely melted. The probe was submerged inside of the reaction mixture and the IR measurements were started. After 5 minutes 20 mol % of NaOH (2 mmol, 80 mg) were added. The reaction was stirred (350 rpm) at 80 C for 1h under solvent-free conditions. Figure S5 3D plot of in situ IR measurements of the reaction between 1a and 3 in the presence of NaOH. S10
11 Figure S6 IR plot of the reaction between 1a and 3 in the presence of NaOH. 4 Synthesis and characterisation of thiazolines In air, a vial was charged with the nitrile (1 mmol), cysteamine hydrochloride (1.5 mmol) and NaOH (0.2 mmol). The reaction was stirred at 80 C for the appropriate time under solvent-free conditions. The crude product was dissolved in ethyl acetate (2 ml) and water (10 ml) was added. The aqueous layer was then extracted with ethyl acetate (3 x 10 ml). The combined organic layers were dried over MgSO 4, filtered and dried under vacuum to give the desired compound. The conversion was determined by GC analysis or by 1 H NMR. 2-Phenyl-4,5-dihydrothiazole, 4a [1] The general procedure yielded to the title compound as a yellow oil (153 mg, 98%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 3H, C ArH) 4.45 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.40 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), 65.5 (s, CH 2), 33.9 (s, CH 2). 2-(4-Fluorophenyl)-4,5-dihydrothiazole, 4b [2] The general procedure yielded to the title compound as a colourless oil (168 mg, 93%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), 4.41 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 3.38 (t, 3 J HH = 8.3 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (d, 1 J CF= Hz, C IV ), (d, 4 J CF= 8.7 Hz, C ArH), (d, 5 J CF= 3.6 Hz, C IV ), (d, 3 J CF= 22.2 Hz, C ArH), 65.3 (s, CH 2), 34.0 (s, CH 2). S11
12 19 F-{ 1 H} NMR (376 MHz, 298K): δ (ppm) = (s, CF). 2-(4-Chlorophenyl)-4,5-dihydrothiazole, 4c [1] The general procedure yielded to the title compound as a colourless solid (179 mg, 91%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), (m, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), 65.6 (s, CH 2), 34.2 (s, CH 2). Melting point: 53 C 2-(4-Bromophenyl)-4,5-dihydrothiazole, 4d [3] The general procedure yielded to the title compound as a colourless solid (228 mg, 94%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), 4.44 (t, 3 J HH = 8.4 Hz, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C IV ), 65.6 (s, CH 2), 34.3 (s, CH 2). Melting point: 91 C 2-p-Tolyl-4,5-dihydrothiazole, 4e [1] The general procedure yielded to the title compound as a colourless solid (158 mg, 89%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), 4.43 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 3.38 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 2.37 (s, 3H, CH 3). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), 65.4 (s, CH 2), 33.9 (s, CH 2), 21.7 (s, CH 3). Melting point: 42 C S12
13 2-(4-Methoxyphenyl)-4,5-dihydrothiazole, 4f [3] The general procedure yielded to the title compound as a yellow solid (188 mg, 97%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), 4.39 (t, 3 J HH = 8.2 Hz, 2H, CH 2), 3.80 (s, 3H, OCH 3), 3.35 (t, 3 J HH = 8.2 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C IV ), (s, C ArH), 65.2 (s, CH 2), 55.5 (s, OCH 3), 33.8 (s, CH 2). Melting point: 53 C 4-(4,5-Dihydrothiazol-2-yl)aniline, 4g [4] The general procedure yielded to the title compound as a pale yellow oil (166 mg, 93%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 2H, C ArH), (m, 2H, CH 2), 3.98 (s, 2H, NH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C IV ), (s, C ArH), 65.1 (s, CH 2), 33.7 (s, CH 2). 2-(3-Bromophenyl)-4,5-dihydrothiazole, 4h [5] The general procedure yielded to the title compound as a pale brown solid (226 mg, 94%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 8.00 (d, 5 J HH = 1.9 Hz, 1H, C ArH), 7.72 (dt, 3 J HH = 7.8 Hz, 5 J HH = 1.4 Hz, 1H, C ArH), 7.57 (dq, 3 J HH = 7.8 Hz, 5 J HH = 1.2 Hz, 1H, C ArH), 7.26 (t, 3 J HH = 7.8 Hz, 1H, C ArH), 4.44 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.42 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 122.8(s, C IV ), 65.5 (s, CH 2), 34.2 (s, CH 2). Melting point: 45 C S13
14 2-m-Tolyl-4,5-dihydrothiazole, 4i [6] The general procedure yielded to the title compound as a colourless oil (150 mg, 85%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.67 (s, 1H, C ArH), 7.62 (d, 3 J HH = 7.3 Hz, 1H, C ArH), (m, 2H, C ArH), 4.43 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.38 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 2.38 (s, 3H, CH 3). 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 65.4 (s, CH 2), 33.8 (s, CH 2), 21.5 (s, CH 3). 3-(4,5-Dihydrothiazol-2-yl)aniline, 4j [1] The general procedure yielded to the title compound as a brown solid (176 mg, 99%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 3H, C ArH), (m, 1H, C ArH), 4.40 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.79 (s, 2H, NH 2), 3.35 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 65.2 (s, CH 2), 33.7 (s, CH 2). Melting point: 66 C 2-(3,5-Difluorophenyl)-4,5-dihydrothiazole, 4k The general procedure yielded to the title compound as a colourless solid (194 mg, 98%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, C ArH), (m, 1H, C ArH), 4.46 (t, 3 J HH = 8.5 Hz, 2H, CH 2), 3.45 (t, 3 J HH = 8.5 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (m, C IV ), (dd, 1 J CF= Hz, 3 J CF= 14.2 Hz, C IV ), (t, 3 J CF= 10.2 Hz, C IV ), (dd, 2 J CF= 19.7 Hz, 4 J CF= 7.9 Hz, C ArH), (t, 2 J CF= 25.6 Hz, C ArH), 65.5 (s, CH 2), 34.4 (s, CH 2). 19 F-{ 1 H} NMR (376 MHz, 298K): δ (ppm) = (s, CF). HRMS calcd. for C9H8F2NS (M+H) found Melting point: 43 C S14
15 2-(2-Chlorophenyl)-4,5-dihydrothiazole, 4l [1] The general procedure yielded to the title compound as a light yellow oil (180 mg, 91%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.60 (dd, 3 J HH = 7.6 Hz, 5 J HH = 1.8 Hz, 1H, C ArH), 7.42 (dd, 3 J HH = 7.9 Hz, 5 J HH = 1.2 Hz, 1H, C ArH), 7.32 (td, 3 J HH = 7.4 Hz, 5 J HH 1.8 Hz, 1H, C ArH), 7.27 (td, 3 J HH = 7.6 Hz, 5 J HH = 1.4 Hz,1H, C ArH), 4.46 (t, 3 J HH = 8.5 Hz, 2H, CH 2), 3.44 (t, 3 J HH = 8.5 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 65.3 (s, CH 2), 34.9 (s, CH 2). 2-(2-Bromophenyl)-4,5-dihydrothiazole, 4m The general procedure yielded to the title compound as a colourless oil (234 mg, 98%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.60 (dd, 3 J HH = 8.0 Hz, 5 J HH = 1.1 Hz, 1H, C ArH), 7.52 (dd, 3 J HH = 7.6 Hz, 5 J HH = 1.8 Hz, 1H, C ArH), 7.31 (td, 3 J HH = 7.6 Hz, 5 J HH = 1.2 Hz, 1H, C ArH), 7.22 (td, 3 J HH = 8.0 Hz, 5 J HH = 1.8 Hz, 1H, C ArH), 4.46 (t, 3 J HH = 8.5 Hz, 2H, CH 2), 3.45 (t, 3 J HH = 8.5 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), (s, C IV ), 65.4 (s, CH 2), 35.1 (s, CH 2). HRMS calcd. for C9H9BrNS (M+H) found (4,5-Dihydrothiazol-2-yl)aniline, 4n [1] The general procedure yielded to the title compound as a pale yellow oil (176 mg, 99%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.47 (d, 3 J HH = 8.0 Hz, 1H, C ArH), 7.16 (t, 3 J HH = 7.5 Hz, 1H, C ArH), (m, 2H, C ArH), 6.17 (s, 2H, NH 2), (m, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), (s, C IV ), 65.5 (s, CH 2), 32.1 (s, CH 2). S15
16 2-(4-Chlorobenzyl)-4,5-dihydrothiazole, 4o [1] The general procedure yielded to the title compound as a yellow oil (194 mg, 92%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.28 (d, 3 J HH = 8.4 Hz, 2H, C ArH), 7.21 (d, 3 J HH = 8.4 Hz, 2H, C ArH), 4.23 (t, 3 J HH = 8.4 HZ, 2H, CH 2), 3.77 (s, 2H, CH 2), 3.26 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), 64.9 (s, CH 2), 40.3 (s, CH 2), 34.5 (s, CH 2). 2-Benzyl-4,5-dihydrothiazole, 4p [1] The general procedure yielded to the title compound as a yellow oil (172 mg, 97%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 5H, C ArH), (m, 2H, CH 2), 3.78 (s, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), 64.6 (s, CH 2), 40.7 (s, CH 2), 34.1 (s, CH 2). 2-(2-Bromobenzyl)-4,5-dihydrothiazole, 4q The general procedure yielded to the title compound as a colourless oil (232 mg, 91%). 1 H NMR (500 MHz, CDCl3, 298K, TMS): δ (ppm) = 7.54 (d, 3 J HH = 7.5 Hz, 1H, C ArH), (m, 1H, C ArH), (m, 1H, C ArH), (m, 1H, C ArH), 4.21 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 3.95 (s, 2H, CH 2), 3.24 (t, 3 J HH = 8.3 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), (s, C IV ), 64.8 (s, CH 2), 40.8 (s, CH 2), 34.2 (s, CH 2). HRMS calcd. for C10H11BrNS (M+H) found (Pyridin-2-yl)-4,5-dihydrothiazole, 4r [1] The general procedure yielded to the title compound as a colourless solid (159 mg, 97%). S16
17 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 8.66 (s, 1H, C ArH), (m, 1H, C ArH), (m, 1H, C ArH), (m, 1H, C ArH), (m, 2H, CH 2), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C ArH), 65.9 (s, CH 2), 32.7 (s, CH 2). Melting point: 92 C 2-(Pyridin-3-yl)-4,5-dihydrothiazole, 4s [1] The general procedure yielded to the title compound as a yellow oil (158 mg, 96%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 9.04 (d, 5 J HH 1.6 Hz, 1H, C ArH), 8.68 (dd, 3 J HH = 4.8 Hz, 5 J HH = 1.6 Hz, 1H,C ArH), 8.10 (dt, 3 J HH = 8.0 Hz, 5 J HH = 1.9 Hz, 1H, C ArH), 7.35 (dd, 3 J HH = 8.0 Hz, 5 J HH = 4.8 Hz, 1H, C ArH), 4.46 (t, 3 J HH = 8.4 Hz, 2H, CH 2), 3.45 (t, 3 J HH = 8.4 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), (s, C IV ), (s, C ArH), 65.2 (s, CH 2), 33.9 (s, CH 2). 2-(Pyridin-4-yl)-4,5-dihydrothiazole, 4t [1] The general procedure yielded to the title compound as a colourless solid (157 mg, 96%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 8.70 (dd, 3 J HH = 4.5 Hz, 5 J HH = 1.7 Hz, 2H, C ArH), 7.67 (dd, 3 J HH = 4.5 Hz, 5 J HH = 1.7 Hz, 2H, C ArH), 4.50 (t, 3 J HH = 8.5 Hz, 2H, CH 2), 3.47 (t, 3 J HH = 8.5 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C ArH), (s, C IV ), (s, C ArH), 65.7 (s, CH 2), 34.2 (s, CH 2). Melting point: 73 C 2-(1H-Pyrrol-2-yl)-4,5-dihydrothiazole, 4u [7] The general procedure yielded to the title compound as a colourless solid (300 mg, 98%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (s, 1H, NH), 6.90 (s, 1H, C ArH), 6.64 (d, 3 J HH = 2.9 Hz, 1H, C ArH), 6.23 (t, 3 J HH = 2.9 Hz, 1H, C ArH), 4.35 (t, 3 J HH = 8.1 Hz, 2H, CH 2), 3.38 (t, 3 J HH = 8.1 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (s, C ArH), (s, C ArH), 64.1 (s, CH 2), 33.7 (s, CH 2). S17
18 Melting point: 94 C 2-(2-Furanyl)-4,5-dihydrothiazole, 4v [6] The general procedure yielded to the title compound as a yellow oil (291 mg, 95%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 1H, C ArH), 6.88 (d, 3 J HH = 3.5 Hz, 1H, C ArH), 6.46 (dd, 3 J HH = 3.5 Hz, 5 J HH 1.8 Hz, 1H, C ArH), 4.37 (t, 3 J HH = 8.3 Hz, 2H, CH 2), 3.34 (t, 3 J HH = 8.3 Hz, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), (s, C IV ), (s, C ArH), (C ArH), (C ArH), 64.5 (s, CH 2), 33.1 (s, CH 2). 2-(Pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w The general procedure yielded to the title compound as a colourless oil (132 mg, 87%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = (m, 2H, CH 2), (m, 2H, CH 2), (m, 2H, CH 2), (m, 2H, CH 2), (m, 1H, CH), (m, 2H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), 83.6 (s, CH), 69.3 (s, C IV ), 64.8 (s, CH 2), 34.0 (s, CH 2), 33.2 (s, CH 2), 26.3 (s, CH 2), 18.1 (s, CH 2). HRMS calcd. for C8H12NS (M+H) found Pentyl-4,5-dihydrothiazole, 4x [8] The general procedure yielded after flash chromatography (SiO 2, penthane/ ethyl acetate 7:3) to the title compound as a colourless oil (85 mg, 55%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 4.21 (tt, 3 J HH = 8.4 Hz, 5 J HH = 1.4 Hz, 2H, CH 2), 3.27 (t, 3 J HH = 8.4 Hz, 2H, CH 2), (m, 2H, CH 2), (m, 2H, CH 2), (m, 4H, CH 2), (m, 3H, CH 3). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), 64.8 (s, CH 2), 34.6 (s, CH 2), 34.0 (s, CH 2), 31.6 (s, CH 2), 27.5 (s, CH 2), 22.6 (s, CH 2), 14.2 (s, CH 3). HRMS calcd. for C8H16NS (M+H) found S18
19 2-Cyclohexyl-4,5-dihydrothiazole, 4y [8] The general procedure yielded after flash chromatography (SiO 2, penthane/ ethyl acetate 8:2) to the title compound as a colourless oil (77 mg, 45%). 1 H NMR (400 MHz, CDCl3, 298K, TMS): δ (ppm) = 4.20 (td, 3 J HH = 8.4 Hz, 5 J HH = 1.1 Hz, 2H, CH 2), 3.22 (t, 3 J HH = 8.4 Hz, 2H, CH 2), (m, 1H, CH), (m, 2H, CH 2), (m, 2H, CH 2), (m, 1H, CH 2), (m, 5H, CH 2). 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K): δ (ppm) = (s, C IV ), 64.7 (s, CH 2), 43.6 (s, CH), 33.3 (s, CH 2), 31.8 (s, CH 2), 26.2 (s, CH 2). S19
20 5 NMR spectra 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-phenyl-4,5-dihydrothiazole, 4a 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K) of 2-phenyl-4,5-dihydrothiazole, 4a S20
21 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b S21
22 19 F-{ 1 H} NMR (376 MHz, 298K) of 2-(4-fluorophenyl)-4,5-dihydrothiazole, 4b S22
23 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-chlorophenyl)-4,5-dihydrothiazole, 4c 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4-chlorophenyl)-4,5-dihydrothiazole, 4c S23
24 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-bromophenyl)-4,5-dihydrothiazole, 4d 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4-bromophenyl)-4,5-dihydrothiazole, 4d S24
25 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-p-tolyl-4,5-dihydrothiazole, 4e 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-p-tolyl-4,5-dihydrothiazole, 4e S25
26 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-(4-methoxyphenyl)-4,5-dihydrothiazole, 4f 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K) of 2-(4-methoxyphenyl)-4,5-dihydrothiazole, 4f S26
27 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 4-(4,5-dihydrothiazol-2-yl)aniline, 4g 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 4-(4,5-dihydrothiazol-2-yl)aniline, 4g S27
28 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(3-bromophenyl)-4,5-dihydrothiazole, 4h 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(3-bromophenyl)-4,5-dihydrothiazole, 4h S28
29 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-m-tolyl-4,5-dihydrothiazole, 4i 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K) of 2-m-tolyl-4,5-dihydrothiazole, 4i S29
30 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 3-(4,5-dihydrothiazol-2-yl)aniline, 4j 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 3-(4,5-dihydrothiazol-2-yl)aniline, 4j S30
31 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k S31
32 19 F-{ 1 H} NMR (376 MHz, 298K) of 2-(3,5-difluorophenyl)-4,5-dihydrothiazole, 4k S32
33 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-(2-chlorophenyl)-4,5-dihydrothiazole, 4l 13 C-{ 1 H} NMR (125.7 MHz, CDCl3, 298K) of 2-(2-chlorophenyl)-4,5-dihydrothiazole, 4l S33
34 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(2-bromophenyl)-4,5-dihydrothiazole, 4m 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(2-bromophenyl)-4,5-dihydrothiazole, 4m S34
35 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4,5-dihydrothiazol-2-yl)aniline, 4n 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4,5-dihydrothiazol-2-yl)aniline, 4n S35
36 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(4-chlorobenzyl)-4,5-dihydrothiazole, 4o 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(4-chlorobenzyl)-4,5-dihydrothiazole, 4o S36
37 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-benzyl-4,5-dihydrothiazole, 4p 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-benzyl-4,5-dihydrothiazole, 4p S37
38 1 H NMR (500 MHz, CDCl3, 298K, TMS) of 2-(2-bromobenzyl)-4,5-dihydrothiazole, 4q 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(2-bromobenzyl)-4,5-dihydrothiazole, 4q S38
39 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(pyridin-2-yl)-4,5-dihydrothiazole, 4r 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(pyridin-2-yl)-4,5-dihydrothiazole, 4r S39
40 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(pyridin-3-yl)-4,5-dihydrothiazole, 4s 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(pyridin-3-yl)-4,5-dihydrothiazole, 4s S40
41 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(pyridin-4-yl)-4,5-dihydrothiazole, 4t 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(pyridin-4-yl)-4,5-dihydrothiazole, 4t S41
42 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(1H-pyrrol-2-yl)-4,5-dihydrothiazole, 4u 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(1H-pyrrol-2-yl)-4,5-dihydrothiazole, 4u S42
43 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(2-furanyl)-4,5-dihydrothiazole, 4v 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(2-furanyl)-4,5-dihydrothiazole, 4v S43
44 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-(pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-(pent-4-yn-1-yl)-4,5-dihydrothiazole, 4w S44
45 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-pentyl-4,5-dihydrothiazole, 4x 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-pentyl-4,5-dihydrothiazole, 4x S45
46 1 H NMR (400 MHz, CDCl3, 298K, TMS) of 2-cyclohexyl-4,5-dihydrothiazole, 4y 13 C-{ 1 H} NMR (75 MHz, CDCl3, 298K) of 2-cyclohexyl-4,5-dihydrothiazole, 4y S46
47 6 References [1] X. Li, B. Zhou, J. Zhang, M. She, S. An, H. Ge, C. Li, B. Yin, J. Li and Z. Shi, Eur. J. Org. Chem. 2012, 8,1626. [2] L. Wu, E-Journal of Chemistry, 2012, 9, [3] U. Pathak, S. Bhattacharyya, V. Dhruwansh, L. K. Pandey, R. Tank and M. V. S. Suryanarayana, Green Chem., 2011, 13, 1648 [4] S. H. Babcock and R. Adams, J. Am. Chem. Soc., 1937, 59, [5] S. F. Hojati, I. Mohammadpoor-Baltork, B. Maleki, M. Gholizadeh, F. Shafiezadeh and M. Haghdous, Can. J. Chemistry, 2010, 88, 135. [6] J. A. Seijas, M. P. Vázquez-Tato, J. Crecente-Campo, Tetrahedron, 2008, 64, [7] B. George, E. P. Papadopoulos, J. Org. Chem., 1977, 42, 441. [8] A. I. Meyers and J. L. Durandetta, J. Org. Chem., 1975, 40, S47
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 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 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 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 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 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
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 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 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 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 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 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 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
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 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 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
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
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 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 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
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 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 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 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 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 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 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. for
Supporting Information for A general synthetic route to [Cu(X)(NHC)] (NHC = N- heterocyclic carbene, X =Cl, Br, I) complexes Orlando Santoro, Alba Collado, Alexandra M. Z. Slawin, Steven P. Nolan and Catherine
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 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 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 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 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 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 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 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 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 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 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 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 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 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 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 περισσότεραSupporting Information for
Supporting Information for A ovel Synthesis of luorinated Pyrazoles via Gold(I)-Catalyzed Tandem Aminofluorination of Alkynes in the Presence of Selectfluor Jianqiang Qian, Yunkui Liu,* Jie Zhu, Bo Jiang,
Διαβάστε περισσότεραESI 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
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 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 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 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 περισσότεραNovel 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
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 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 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 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 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 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 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 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 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 περισσότεραEur. J. Inorg. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007 ISSN SUPPORTING INFORMATION
Eur. J. Inorg. Chem. 2007 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 ISSN 1434 1948 SUPPORTING INFORMATION Title: Synthesis of Cyclic Carbonates from Atmospheric Pressure Carbon Dioxide Using
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 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 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 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions
Διαβάστε περισσότεραSUPPLEMENTARY MATERIAL
10.1071/CH16014_AC The Authors 2016 Australian Journal of Chemistry 2016, 69(9), 1049-1053 SUPPLEMENTARY MATERIAL A Green Approach for the Synthesis of Novel 7,11-Dihydro-6H-chromeno[3,4- e]isoxazolo[5,4-b]pyridin-6-one
Διαβάστε περισσότεραFast 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
Διαβάστε περισσότεραChiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic Aminations. Minyang Zhuang and Haifeng Du*
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Chiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic
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 περισσότεραSupporting Information
Supporting Information Visible Light Initiated Hantzsch Synthesis of 2,5-Diaryl Substituted Pyrroles at Ambient Conditions Tao Lei, Wen-Qiang Liu, Jian Li, Mao-Yong Huang, Bing Yang, Qing-Yuan Meng, Bin
Διαβάστε περισσότεραLigand-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
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 περισσότεραSupporting Information
Supporting Information Nano WO3-supported sulfonic acid: New, efficient and high recyclable heterogeneous nano catalyst Ali Amoozadeh* and Salman Rahmani* Department of Chemistry, Semnan University, Semnan,
Διαβάστε περισσότεραSupporting Information
Supporting Information An Approach to 3,6-Disubstituted 2,5-Dioxybenzoquinones via Two Sequential Suzuki Couplings. Three-step Synthesis of Leucomelone Xianwen Gan, Wei Jiang, Wei Wang,,,* Lihong Hu,,*
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 περισσότεραElectronic 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*
Διαβάστε περισσότεραSUPPLEMENTARY DATA. Waste-to-useful: Biowaste-derived heterogeneous catalyst for a green and sustainable Henry reaction
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 209 SUPPLEMENTARY DATA Waste-to-useful:
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 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 περισσότεραSupplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;
Supplementary Data Synthesis, Chemo-selective Properties of Substituted 9-Aryl-9H-fluorenes from Triarylcarbinols and Enantiomerical Kinetics of Chiral 9-Methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 204 Supporting information Palladium nanoparticles supported on triazine functionalised mesoporous
Διαβάστε περισσότεραCatalyst-free transformation of levulinic acid into pyrrolidinones with formic acid
Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid Yawen Wei, a Chao Wang,* a Xue Jiang, a Dong Xue, a Zhao-Tie Liu, a and Jianliang Xiao* a,b a Key Laboratory of Applied
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
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
Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
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 περισσότεραD-Glucosamine-derived copper catalyst for Ullmann-type C- N coupling reaction: theoretical and experimental study
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 D-Glucosamine-derived copper catalyst for Ullmann-type C- N coupling reaction: theoretical
Διαβάστε περισσότεραSelective 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
Διαβάστε περισσότεραSynthesis 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
Διαβάστε περισσότεραProtease-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,
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 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 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 for
Supplementary Information for Organocatalytic Asymmetric Intramolecular [3+2] Cycloaddition: A Straightforward Approach to Access Multiply Substituted Hexahydrochromeno[4,3-b]pyrrolidine Derivatives in
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 περισσότεραPhosphorus 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
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 περισσότεραusing metal-organic framework Cu-MOF-74 as an efficient heterogeneous catalyst Hanh T. H. Nguyen, Oanh T. K. Nguyen, Thanh Truong *, Nam T. S.
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Synthesis of imidazo[1,5-a]pyridines via oxidative amination of C(sp 3 )-H bond under air using
Διαβάστε περισσότεραSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2014 A Family of Click Nucleosides for Metal-Mediated Base Pairing: Unravelling the Principles of Highly Stabilizing Metal-Mediated
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 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 περισσότερα