Copper-Catalyzed Cascade Cycloamination of alpha-csp 3 -H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines. Supporting Information
|
|
- Douglas Harrington
- 5 years ago
- Views:
Transcription
1 Copper-Catalyzed Cascade Cycloamination of alpha-csp 3 -H Bond of N-Aryl Ketimines with Azides: Access to Quinoxalines Tengfei Chen, Xun Chen, Jun Wei, Dongen Lin *, Ying Xie, and Wei Zeng * School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou , China Table of Contents Supporting Information 1. General experimental information Table 1. Catalyst screening for copper-catalyzed alpha- Csp 3 -H bond cycloamination of N-aryl ketimine 1a a Table 2. The effect of the solvent on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a Table 3. The effect of the azide on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a Table 4. The effect of the oxidant on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a Table 5. The effect of the proton source on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a General procedure for the synthesis of N-phenylketimines General procedure for synthesis of quinoxaline derivatives (2a-2z) Synthesis of (Z)-N-(4-methoxyphenyl)benzimidoyl cyanide (3) Control experiments for mechanism studies References H NMR and 13 C NMR spectrum for all isolated products
2 1. General experimental information All reactions were carried out in flame-dried sealed tubes with magnetic stirring. Unless otherwise noted, all experiments were performed under argon atmosphere. All reagents were purchased from TCI, Acros or Strem. Solvents were treated with 4 Å molecular sieves or sodium and distilled prior to use. Purifications of reaction products were carried out by flash chromatography using Qingdao Haiyang Chemical Co. Ltd silica gel (40-63 mm). 1 H NMR and 13 C NMR spectra were recorded with tetramethylsilane (TMS) as internal standard at ambient temperature unless otherwise indicated on a Bruker Avance DPX 600 fourier Transform spectrometer operating at 400 MHz for 1 H NMR and 100 MHz for 13 C NMR. Chemical shifts are reported in parts per million (ppm) and coupling constants are reported as Hertz (Hz). Splitting patterns are designated as singlet (s), broad singlet (bs), doublet (d), triplet (t). Splitting patterns that could not be interpreted or easily visualized are designated as multiple (m). Low resolution mass spectra were recorded using a Waters HPLC/ZQ4000 Mass Spectrometer.Gas chromatograph mass spectra were obtained with a SHIMADZU model GCMS-QP5000 spectrometer. 2
3 1.1. Table 1. Catalyst screening for copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a Entry Catalyst Yield (%) b 1 CuO 19 2 CuBr trace 3 CuBr 2 trace 4 CuI 5 5 CuCl CuCl 0 7 Cu(OAC) CuSO Cu(OTf) Cu(TFA) Cu 2 (BF 4 )H 2 O 0 a The reactions were carried out using N-aryl ketimine 1a (0.1 mmol), NaN 3 (0.3 mmol) with Cu catalyst (10 mol%) in the presence of PIDA (0.3 mmol) and AcOH (0.2 mmol) in solvent (2.0 ml) at 25 o C for 16 h in a sealed reaction tube under Ar, followed by flash chromatography on SiO 2. b Isolated yield Table 2. The effect of the solvent on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a Entry Solvent Yield (%) b 1 CH 2 Cl ClCH 2 CH 2 Cl 9 3 CH 3 CH 2 OH 0 4 1,4-dioxane 14 5 EtOAc 19 6 CHCl toluene 14 8 THF 9 9 CH 3 CN 5 10 CH 3 OCH 3 9 a The reactions were carried out using N-aryl ketimine 1a (0.1 mmol), NaN 3 (0.3 mmol) with CuO 3
4 (10 mol%) in the presence of PIDA (0.3 mmol) and AcOH (0.2 mmol) in given solvent (2.0 ml) at 25 o C for 16 h in a sealed reaction tube under Ar, followed by flash chromatography on SiO 2. b Isolated yield Table 3. The effect of the azide on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a Entry Azide Yield (%) b 1 NaN TsN PhCON TMSN PhN 3 0 a The reactions were carried out using N-aryl ketimine 1a (0.1 mmol), azide (0.3 mmol) with CuO (10 mol%) in the presence of PIDA (0.3 mmol) and AcOH (0.2 mmol) in EtOAc (2.0 ml) at 25 o C for 16 h in a sealed reaction tube under Ar, followed by flash chromatography on SiO 2. b Isolated yield 1.4. Table 4. The effect of the oxidant on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a Entry Oxidant Yield (%) b 1 benzoquinnone 0 2 PhIO 0 3 MnO NaS 2 O AgOAc 19 6 Ag 2 CO PhI(OAc) PhI(OOCF 3 ) 2 0 a The reactions were carried out using N-aryl ketimine 1a (0.1 mmol), NaN 3 (0.3 mmol) with CuO (10 mol%) in the presence of oxidant (0.3 mmol) and AcOH (0.2 mmol) in EtOAc (2.0 ml) at 25 o C for 16 h in a sealed reaction tube under Ar, followed by flash chromatography on SiO 2. b Isolated yield. 4
5 1.5. Table 5. The effect of the proton source on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1a a Entry Acid Yield (%) b 1 CH 3 COOH 49 2 CF 3 SO 3 H 0 3 PhCOOH 29 4 PivOH 71 5 TsOH 0 6 iproh 0 a The reactions were carried out using N-aryl ketimine 1a (0.1 mmol), NaN 3 (0.3 mmol) with CuO (10 mol%) in the presence of PIDA (0.3 mmol) and acid (0.2 mmol) in EtOAc (2.0 ml) at 25 o C for 16 h in a sealed reaction tube under Ar, followed by flash chromatography on SiO 2. b Isolated yield. 1.6 General procedure for the synthesis of N-aryl ketimines 3 R R 1 + NH 2 O R 1 10 mol % H 2 SO 4 N toluene, reflux R 3 R 2 R 2 The mixture of acetophenone derivatives (0.2 mmol, 1.0 equiv.) and substituted anilines (0.2 mmol, 1.0 equiv.) was stirred in toluene (3.0 ml) at 120 o C for 24 h in the presence of molecular sieve (4 Å) (0.40 g) and a catalytic amount of concentrated H 2 SO 4 (10 mol%). The mixture was then filtered and the solvent was removed under reduced pressure to produce the corresponding crude N-aryl ketimines. These crude N-aryl ketimines could be directly used for synthetic purpose without further purification because these N-aryl ketimines are easily decomposed on silica gel. [1] 1.7 General procedure for synthesis of quinoxaline derivatives (2a-2z) To the solution of N-aryl ketimines 1 (0.1 mmol) in dry EtOAc (2.0 ml) were added CuO (0.8 mg, 10 mol%), NaN 3 (19.5 mg, 0.3 mmol), PIDA (96.6 mg, 0.3 mmol) and PivOH ( 20.4 mg, 0.2 mmol) under Ar atmosphere, and then the corresponding reaction mixture was stirred in a sealed tube at 25 o C for 16 h. After the starting materials were disappeared, then the mixture was filtered, and the corresponding organic layers were concentrated under vacuum, and the resulting crude product was purified by flash column chromatography using 10 20% (v/v) ethyl acetate in petroleum ether as eluent to afford the desired phenylquinoxaline 2 as a white solid. 5
6 2a 2-Phenylquinoxaline (2a) [2] : White solid; 15 mg, 71% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.30 (s, 1H), 8.13 (ddd, J = 14.0, 11.8, 4.2 Hz, 4H), (m, 2H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 151.8, 143.3, 142.3, 141.6, 136.7, 130.2, 130.2, 129.6, 129.5, 129.1, MS (ESI): m/z = [M] +. 2b 2-(p-Tolyl)quinoxaline (2b) [2] : White solid; 17 mg, 77% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.29 (s, 1H), 8.10 (dd, J = 15.9, 8.2 Hz, 4H), 7.72 (ddd, J = 15.2, 13.8, 6.8 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 2.43 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 151.0, 143.2, 141.6, 140.7, 140.1, 136.9, 132.6, 129.9, 129.1, 129.1, 127.9, 127.4, MS (ESI): m/z = [M] +. 2c 2-(4-Methoxyphenyl)quinoxaline (2c) [2] : White solid; 19 mg, 80% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.29 (s, 1H), 8.17 (d, J = 8.1 Hz, 2H), 8.10 (t, J = 9.0 Hz, 2H), 7.73 (dt, J = 14.5, 7.0 Hz, 2H), 7.08 (d, J = 8.1 Hz, 2H), 3.90 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 161.5, 151.5, 143.1, 142.3, 141.2, 130.1, 129.4, 129.3, 129.0, 128.9, 114.6, 99.9, MS (ESI): m/z = [M] +. 2d 2-(4-Fluorophenyl)quinoxaline (2d) [3] : White solid; 16 mg, 68% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.29 (s, 1H), 8.20 (dd, J = 8.7, 5.4 Hz, 2H), 8.13 (dd, J = 11.0, 4.0 Hz, 2H), (m, 2H), 7.25 (dd, J = 10.5, 6.7 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = Hz), 150.7, 142.9, 142.2, 141.5, (d, J = 1.0 Hz), 130.4, 129.5, 129.5, 129.4, 129.1, (d, J = 22.2 Hz). MS (ESI): m/z = [M] +. 6
7 2e 2-(4-Chlorophenyl)quinoxaline (2e) [2] : Yellow solid; 16 mg, 68% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.31 (s, 1H), 8.17 (d, J = 7.4 Hz, 4H), 7.79 (t, J = 7.7 Hz, 2H), 7.55 (d, J = 7.8 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 150.6, 142.8, 142.2, 141.6, 136.6, 135.1, 130.5, 129.7, 129.6, 129.3, 129.1, MS (ESI): m/z = [M] +. 2f 2-(4-Bromophenyl)quinoxaline (2f) [2] : Yellow solid; 17 mg, 60% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.26 (s, 1H), 8.10 (t, J = 6.7 Hz, 2H), 8.05 (d, J = 8.3 Hz, 2H), (m, 2H), 7.66 (d, J = 8.3 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 150.5, 142.7, 142.1, 141.6, 135.5, 132.3, 130.4, 129.8, 129.6, 129.1, 128.9, MS (ESI): m/z = [M] +. 2g 4-(Quinoxalin-2-yl)benzonitrile (2g) [3] : Yellow solid; 12 mg, 52% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.28 (s, 1H), 8.27 (d, J = 8.1 Hz, 2H), 8.09 (t, J = 6.1 Hz, 2H), (m, 4H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , MS (ESI): m/z = [M] +. 2h 2-(4-Nitrophenyl)quinoxaline (2h) [3] : Yellow solid; 14 mg, 56% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.39 (s, 1H), (m, 4H), (m, 2H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , MS (ESI): m/z = [M] +. 7
8 2i Methyl 4-(quinoxalin-2-yl)benzoate (2i) [4] : White solid; 15 mg, 57% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.27 (s, 1H), 8.11 (ddd, J = 20.0, 17.9, 8.3 Hz, 6H), 7.70 (t, J = 6.6 Hz, 2H), 3.89 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 166.6, 150.5, 143.1, 142.2, 141.8, 140.7, 131.4, 130.5, 130.3, 130.0, , 129.2, 127.5, MS (ESI): m/z = [M] +. 2j 2-(3-Methoxyphenyl)quinoxaline (2j) [3] : White solid; 16 mg, 65% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.29 (s, 1H), 8.12 (dd, J = 15.0, 8.1 Hz, 2H), (m, 4H), 7.44 (t, J = 8.0 Hz, 1H), 7.04 (dd, J = 8.2, 2.0 Hz, 1H), 3.91 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 160.3, 151.5, 143.4, 142.2, 141.6, 138.1, 130.2, 130.1, 129.6, 129.5, 129.1, 119.9, 116.2, 112.7, MS (ESI): m/z = [M] +. 2k 2-(3-Chlorophenyl)quinoxaline (2k) [2] : White solid; 17 mg, 66% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.30 (s, 1H), 8.23 (s, 1H), 8.15 (t, J = 9.0 Hz, 2H), 8.06 (s, 1H), (m, 2H), 7.50 (d, J = 3.7 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 150.3, 142.9, 142.2, 141.8, 138.5, 135.3, 130.5, 130.3, 130.2, 129.9, 129.6, 129.1, 127.6, MS (ESI): m/z = [M] +. 2l 2-(2-Methoxyphenyl)quinoxaline (2l) [2] : Red solid; 13 mg, 55% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.34 (s, 1H), (m, 2H), 7.90 (dd, J = 7.6, 1.6 Hz, 1H), (m, 2H), (m, 1H), 7.14 (t, J = 7.4 Hz, 1H), 7.02 (d, J = 8.3 Hz, 1H), 3.86 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ , , , , , , , , , , , , 8
9 121.51, , MS (ESI): m/z = [M] +. 2m 2-(2-Chlorophenyl)quinoxaline (2m) [2] : Yellow solid; 12 mg, 50% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.21 (s, 1H), (m, 2H), 7.78 (dd, J = 6.4, 3.4 Hz, 2H), (m, 1H), (m, 1H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 152.3, 146.1, 142.2, 141.3, 136.5, 132.5, 131.9, 130.8, 130.2, 130.2, 130.1, 129.6, 129.2, MS (ESI): m/z = [M] +. 2n 2-(Quinoxalin-2-yl)phenol (2n) [5] : White solid; 10 mg, 45% yield; 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 9.51 (s, 1H), 8.09 (ddd, J = 14.6, 7.9, 1.1 Hz, 2H), 8.01 (dd, J = 8.1, 1.1 Hz, 1H), (m, 2H), (m, 1H), 7.11 (dd, J = 8.3, 0.7 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 160.9, 151.8, 142.6, 140.8, 138.3, 132.9, 131.0, 129.6, 129.3, 127.5, 126.7, 119.4, 118.8, MS (ESI): m/z = [M] +. 2o 6-Methoxy-2-phenylquinoxaline (2o) [2] : White solid; 20 mg, 85% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.25 (s, 1H), 8.16 (d, J = 8.0 Hz, 2H), 8.04 (d, J = 9.1 Hz, 1H), 7.56 (t, J = 7.6 Hz, 2H), (m, 1H), (m, 2H), 3.99 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 160.5, 149.6, 143.1, 143.0, 138.4, 136.9, 130.5, 129.7, 129.0, 127.1, 123.5, 106.5, MS (ESI): m/z = [M] +. 2p 6-Methyl-2-phenylquinoxaline (2p) [2] : White solid; 18 mg, 82% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.26 (s, 1H), 8.16 (d, J = 7.4 Hz, 2H), 8.03 (d, J = 8.5 Hz, 1H), 7.87 (s, 1H), (m, 4H), 2.59 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 151.0, 143.2, 141.6, 140.7, 140.1, 136.9, 132.5, 129.9, 129.1, 129.1, 127.9, 127.4, MS (ESI): m/z = [M] +. 9
10 2q 6-Fluoro-2-phenylquinoxaline (2q) [3] : White solid; 9 mg, 40% yield ; 1 H NMR (400 MHz, CDCl 3 ) δ 9.22 (s, 1H), (m, 3H), 7.65 (dd, J = 9.0, 2.5 Hz, 1H), (m, 4H); 13 C NMR (100 MHz, CDCl 3 ) δ (d, J = Hz), 151.3, 144.0, (d, J = 13.1 Hz), 139.5, 136.5, (d, J = 10.1 Hz), 130.2, 129.2, 127.4, (d, J = 26.3 Hz), (d, J = 22.2 Hz). MS (ESI): m/z = [M] +. 2r 6-Bromo-2-phenylquinoxaline (2r) [2] : White solid; 8 mg, 33% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.25 (s, 1H), 8.11 (d, J = 7.5 Hz, 2H), (m, 2H), 7.65 (d, J = 9.0 Hz, 1H), 7.48 (p, J = 6.6 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 151.9, 144.1, 141.8, 140.8, 136.4, 135.3, 131.3, 130.9, 130.4, 129.2, 128.1, MS (ESI): m/z = [M] +. 2s 6-Chloro-2-phenylquinoxaline (2s) [2] : White solid; 10 mg, 35% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.23 (s, 1H), 8.21 (s, 1H), 8.10 (d, J = 7.5 Hz, 2H), 7.93 (d, J = 8.9 Hz, 1H), 7.77 (d, J = 8.9 Hz, 1H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 152.0, 144.1, 142.1, 141.1, 136.4, 133.8, 131.5, 130.9, 130.5, 129.2, 127.5, MS (ESI): m/z = [M] +. 2t 8-Methoxy-2-phenylquinoxaline (2t) [2] : White solid; 17 mg, 72% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.33 (s, 1H), 8.20 (d, J = 7.7 Hz, 2H), (m, 2H), (m, 3H), 7.13 (d, J = 7.6 Hz, 1H), 4.12 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 155.4, 150.7, 143.6, 142.4, 136.8, 134.5, 130.0, 129.6, 129.1, 127.7, 120.9, 108.6, MS (ESI): m/z = [M] +. 10
11 2u 2-(Pyridin-4-yl)quinoxaline (2u) [6] : Yellow solid; 12 mg, 57% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.33 (s, 1H), 8.82 (d, J = 3.8 Hz, 2H), 8.14 (d, J = 6.7 Hz, 2H), 8.07 (d, J = 4.0 Hz, 2H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ 150.7, 149.0, 143.8, 142.6, 142.3, 142.2, 130.7, 130.6, 129.8, 129.2, MS (ESI): m/z = [M] +. 2v 2-(Pyridin-2-yl)quinoxaline (2v) [6] : Yellow solid; 11 mg, 53% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.93 (s, 1H), 8.72 (d, J = 4.4 Hz, 1H), 8.51 (d, J = 7.9 Hz, 1H), 8.10 (ddd, J = 9.9, 5.3, 1.9 Hz, 2H), 7.80 (td, J = 7.8, 1.4 Hz, 1H), 7.71 (d, J = 4.9 Hz, 2H), 7.32 (dd, J = 7.0, 5.1 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 154.4, 150.0, 149.3, 144.0, 142.4, 141.6, 136.9, 130.0, 129.9, 129.6, 129.2, 124.5, MS (ESI): m/z = [M] +. 2w 2-(Furan-2-yl)quinoxaline (2w) [3] : Yellow solid; 10 mg, 51% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.25 (s, 1H), (m, 2H), (m, 3H), 7.32 (s, 1H), 6.63 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 151.6, 145.1, 143.9, 142.1, 141.3, 130.5, 129.3, 129.2, 112.5, MS (ESI): m/z = [M] +. 2x 2-(Thiophen-2-yl)quinoxaline (2x) [3] : White solid; 10 mg, 47% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 9.24 (s, 1H), 8.06 (dd, J = 8.2, 2.4 Hz, 2H), 7.86 (d, J = 3.6 Hz, 1H), (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 147.4, 142.3, 142.2, 142.1, 141.4, 130.4, 129.8, 129.2, 129.1, 128.5, MS (ESI): m/z = [M] +. 11
12 2y 2-Chloro-3-phenylquinoxaline (2y) [7] : White solid; 8 mg, 33% yield; 1 H NMR (400 MHz, DMSO) δ (m, 1H), (m, 1H), (m, 2H), 7.84 (d, J = 2.9 Hz, 2H), 7.57 (d, J = 2.7 Hz, 3H); 13 C NMR (100 MHz, DMSO) δ , , , , , , , , , , , MS (ESI): m/z = [M] +. 2z 2-Methyl-3-phenylquinoxaline (2z) [8] : White solid; 14 mg, 62% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 8.12 (d, J = 7.7 Hz, 1H), 8.06 (d, J = 7.7 Hz, 1H), (m, 2H), 7.66 (d, J = 7.1 Hz, 2H), (m, 3H), 2.78 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 154.9, 152.6, 141.3, 141.0, 139.1, 129.7, 129.2, 129.0, 128.9, 128.6, 128.3, MS (ESI): m/z = [M] z 2,3-Diphenylquinoxaline (2-1z) [8] : White solid; 9 mg, 31% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 8.18 (dd, J = 6.0, 3.4 Hz, 2H), 7.76 (dd, J = 6.1, 3.3 Hz, 2H), 7.52 (d, J = 6.4 Hz, 4H), 7.34 (d, J = 6.9 Hz, 6H); 13 C NMR (100 MHz, CDCl 3) δ 153.5, 141.3, 139.1, 130.0, 129.9, 129.2, 128.8, MS (ESI): m/z = [M] z 2-Benzyl-3-phenylquinoxaline (2-2z) [8] : White solid; 19 mg, 80% yield; 1H NMR (400 MHz, CDCl3) δ (m, 2H), (m, 2H), 7.43 (s, 5H), (m, 3H), 6.98 (d, J = 7.1 Hz, 2H), 4.40 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 141.4, 141.0, 139.0, 138.2, 129.8, 129.6, 129.2, 129.0, 128.9, 128.9, 128.5, 128.3, 126.4, MS (ESI): m/z = [M] +. 12
13 1.8 Synthesis of (Z)-N-(4-methoxyphenyl)benzimidoyl cyanide (3) The mixture of (E)-4-methoxy-N-(1-phenylethylidene)aniline (1a) (0.2 mmol, 45.0 mg), azidotrimethylsilane (0.4 mmol, 48.0 mg), sodium bromide (0.4 mmol, 41.0 mg), iodobenzene diacetate (0.6 mmol, mg), DMSO (2.0 ml) was stirred at 20 o C under air. After 12 hours, water (5 ml) was added to the mixture and extracted with ethyl acetate (10.0 ml 3). Dried with anhydrous magnesium sulfate and concentrated and purified by flash chromatography on silicon gel to afford 3 as yellow solid. 3 (Z)-N-(4-Methoxyphenyl)benzimidoyl cyanide (3) [9] : Yellow solid; 38 mg, 80% yield; 1 H NMR (400 MHz, CDCl 3 ) δ 8.13 (d, J = 7.5 Hz, 1H), (m, 1H), 7.33 (d, J = 8.9 Hz, 1H), 7.00 (d, J = 8.9 Hz, 1H), 3.86 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 159.5, 141.8, 136.9, 134.1, 132.4, 129.0, 127.9, 123.0, 114.5, 111.7, MS (ESI): m/z = [M] Control experiments for mechanism studies (a) PIDA-promoted alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1o To the solution of N-phenylketoimines 1o (0.1 mmol) in dry EtOAc (2.0 ml) were added NaN 3 (19.5 mg, 0.3 mmol), PIDA (96.6 mg, 0.3 mmol) and PivOH (20.4 mg, 0.2 mmol) under Ar atmosphere, and then the corresponding reaction mixture was stirred in a sealed tube at 25 o C for 16 h. Both desired 2o and 4 were not observed under these conditions. (b) Control experiment for this transformation using cyanide 3 as starting material To the solution of (Z)-N-(4-methoxyphenyl)benzimidoyl cyanide 3 (0.1 mmol) in dry EtOAc (2.0 ml) were added CuO (0.8 mg, 10 mol %) NaN 3 (19.5 mg, 0.3 mmol), PIDA (96.6 mg, 0.3 mmol) and PivOH (20.4 mg, 0.2 mmol) under Ar atmosphere, and then the corresponding reaction 13
14 mixture was stirred in a sealed tube at 25 o C for 16 h. The desired 2o were not observed under standard conditions, and substrate 3 was recovered in 87% yield. (c): The effect of TEMPO on the copper-catalyzed alpha-csp 3 -H bond cycloamination of N-aryl ketimine 1o To the solution of N-arylketoimines 1o (0.1 mmol) in dry EtOAc (2.0 ml) were added CuO (0.8 mg, 10 mol%),nan 3 (19.5 mg, 0.3 mmol), PIDA (96.6 mg, 0.3 mmol),pivoh (20.4 mg, 0.2 mmol) and TEMPO (31.2 mg,0.2 mmol) under Ar atmosphere, and then the corresponding reaction mixture was stirred in a sealed tube at 25 o C for 16 h. The desired 2o were not observed under these conditions. 3. References 1. Ye, W.; Indubhusan, D.; Naohiko, Y. J. Am. Chem. Soc. 2012, 134, Nguyen, T. B.; Retailleau, P.; Al-Mourabit. A. Org. Lett. 2013, 15, Vadagaonkar, K. S.; Kalmode, H, P.; Murugan, K.; Chaskar, A. C. RSC Adv. 2015, 5, Leclerc, J.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, Madhav, B.; Murthy, S. N.; Reddy, V. P.; Rao, K. R.; Nageswar, Y. V. D. Tetrahedron Lett. 2009, 50, Jung, D.; Song, J.; Kim, Y.; Lee, D.; Lee,Y.; Park, Y.; Choi, S.; Hahn J. Bull. Korean Chem. Soc. 2007, 28, Rao, K. R.; Raghunadha, A.; Kalitaa, D.; Laxminarayanab, E.; Palc, M.; Meruva, S. B. Der Pharma Chemica. 2015, 7, Lassagne, F.; Chevalliera,F.; Roisnelb, T.; Dorcetb, V.; Mongin, F.; Domingo, L. R. synthesis 2015, 47, Chen, F.; Huang, X.; Cui, Y.; Jiao, N. Chem.-Eur. J. 2013, 19,
15 4. 1 H NMR and 13 C NMR spectrum for all isolated products. 1) The 1 H NMR and 13 C NMR spectrum for 2a (Using CDCl 3 as solvent) 15
16 2) The 1 H NMR and 13 C NMR spectrum for 2b (Using CDCl 3 as solvent) 16
17 3) The 1 H NMR and 13 C NMR spectrum for 2c (Using CDCl 3 as solvent) 17
18 4) The 1 H NMR and 13 C NMR spectrum for 2d (Using CDCl 3 as solvent) 18
19 5) The 1 H NMR and 13 C NMR spectrum for 2e (Using CDCl 3 as solvent) 19
20 6) The 1 H NMR and 13 C NMR spectrum for 2f (Using CDCl 3 as solvent) 20
21 7) The 1 H NMR and 13 C NMR spectrum for 2g (Using CDCl 3 as solvent) 21
22 8) The 1 H NMR and 13 C NMR spectrum for 2h (Using CDCl 3 as solvent) 22
23 9) The 1 H NMR and 13 C NMR spectrum for 2i (Using CDCl 3 as solvent) 23
24 10) The 1 H NMR and 13 C NMR spectrum for 2j (Using CDCl 3 as solvent) 24
25 11) The 1 H NMR and 13 C NMR spectrum for 2k (Using CDCl 3 as solvent) 25
26 12) The 1 H NMR and 13 C NMR spectrum for 2l (Using CDCl 3 as solvent) 26
27 13) The 1 H NMR and 13 C NMR spectrum for 2m (Using CDCl 3 as solvent) 27
28 14) The 1 H NMR and 13 C NMR spectrum for 2n (Using CDCl 3 as solvent) 28
29 15) The 1 H NMR and 13 C NMR spectrum for 2o (Using CDCl 3 as solvent) 29
30 16) The 1 H NMR and 13 C NMR spectrum for 2p (Using CDCl 3 as solvent) 30
31 17) The 1 H NMR and 13 C NMR spectrum for 2q (Using CDCl 3 as solvent) 31
32 18) The 1 H NMR and 13 C NMR spectrum for 2r (Using CDCl 3 as solvent) 32
33 19) The 1 H NMR and 13 C NMR spectrum for 2s (Using CDCl 3 as solvent) 33
34 20) The 1 H NMR and 13 C NMR spectrum for 2t (Using CDCl 3 as solvent) 34
35 21) The 1 H NMR and 13 C NMR spectrum for 2u (Using CDCl 3 as solvent) 35
36 22) The 1 H NMR and 13 C NMR spectrum for 2v (Using CDCl 3 as solvent) 36
37 23) The 1 H NMR and 13 C NMR spectrum for 2w (Using CDCl 3 as solvent) 37
38 24) The 1 H NMR and 13 C NMR spectrum for 2x (Using CDCl 3 as solvent) 38
39 25) The 1 H NMR and 13 C NMR spectrum for 2y (Using DMSO-d6 as solvent) 39
40 26) The 1 H NMR and 13 C NMR spectrum for 2z (Using CDCl 3 as solvent) 40
41 27) The 1 H NMR and 13 C NMR spectrum for 2-1z (Using CDCl 3 as solvent) 41
42 28) The 1 H NMR and 13 C NMR spectrum for 2-2z (Using CDCl 3 as solvent) 42
43 29) The 1 H NMR and 13 C NMR spectrum for 3 (Using CDCl 3 as solvent) 43
44 44
p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of
Supporting Information for: p-toluenesulfonic Acid-Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN 3 for Synthesis of 4-Aryl-NH-1,2,3-triazoles Xue-Jing Quan, Zhi-Hui Ren, Yao-Yu Wang, and
More informationSupporting Information
Palladium-Catalyzed Cascade Oxidantion/sp 2 C-H Acylation of Azoarenes with Aryl Methanes Feng Xiong, a Cheng Qian, b Dongen Lin, b Wei Zeng b,* and Xiaoxia Lu a,* a Chengdu Institute of Biology,CAS, Chengdu
More informationRegioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation
Regioective Halogenation of 2-Substituted-1,2,3-Triazole via sp 2 C-H Activation Qingshan Tian, Xianmin Chen, Wei Liu, Zechao Wang, Suping Shi, Chunxiang Kuang,* Department of Chemistry, Tongji University,
More informationSimple copper/tempo catalyzed aerobic dehydrogenation. of benzylic amines and anilines
Simple copper/tempo catalyzed aerobic dehydrogenation of benzylic amines and anilines Zhenzhong Hu and Francesca M. Kerton,* Department of Chemistry, Memorial University of Newfoundland, St. John s, NL,
More informationSupporting Information
Supporting Information Direct Synthesis of Benzimidazoles by Dehydrogenative Coupling of Aromatic Diamines and Alcohols Catalyzed by Cobalt Prosenjit Daw, Yehoshoa Ben-David, and David Milstein* Department
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Supporting Information Facile Three-Step Synthesis and Photophysical Properties of [8]-, [9]-,
More informationSupporting Information. Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition
Supporting Information Copper-catalyzed cascade synthesis of benzimidazoquinazoline derivatives under mild condition Shan Xu, Juyou Lu and Hua Fu* Key Laboratory of Bioorganic Phosphorus Chemistry and
More informationSupporting Information. Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base
Supporting Information Efficient copper-catalyzed Michael addition of acrylic derivatives with primary alcohols in the presence of base Feng Wang, a Haijun Yang, b Hua Fu, b,c * and Zhichao Pei a * a College
More informationSupporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylin
Supporting Information Synthesis of 2-Aminobenzonitriles through Nitrosation Reaction and Sequential Iron(III)-Catalyzed C C Bond Cleavage of 2-Arylindoles Wei-Li Chen, Si-Yi Wu, Xue-Ling Mo, Liu-Xu Wei,
More informationEfficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide as the Acetylene Source
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Efficient Metal-Free Pathway to Vinyl Thioesters with Calcium Carbide
More informationSupporting Information
Supporting Information B(C 6 F 5 ) 3 -catalyzed Regioselective Deuteration of Electronrich Aromatic and Heteroaromatic compounds Wu Li, Ming-Ming Wang, Yuya Hu and Thomas Werner* Leibniz-Institute of Catalysis
More informationSupporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2016 Supporting Information Fangyi Li, Changgui Zhao, and Jian Wang* Department of Pharmacology
More informationSupplementary Materials Contents
Supplementary Materials Contents Supporting information... S1 1. General Information & Materials... S2 2. General Procedure for ptimization of Amidation of Aryl Bromides with Copper/,-Dimethylglycine Catalytic
More informationSupporting Information. Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as
Supporting Information Palladium-Catalyzed Formylation of Aryl Iodides with HCOOH as CO Source Guanglong Sun,,, Xue Lv,,, Yinan Zhang, Min Lei,*,, and Lihong Hu*, Jiangsu Key Laboratory for Functional
More informationSupporting Information
Supporting Information Cobalt-Catalyzed Carbonylation of C(sp 2 )-H Bonds with Azodicarboxylate as the Carbonyl Source Jiabin Ni,, Jie Li,,š Zhoulong Fan,, and Ao Zhang *,,,š CAS Key Laboratory of Receptor
More informationSupporting Information for. Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of. 3,5-Disubstituted Pyridines: Mechanistic Studies
Supporting Information for Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3,5-Disubstituted Pyridines: Mechanistic Studies Ta-Hsien Chuang* a, Yu-Chi Chen b and Someshwar Pola
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information ovel pseudo[2]rotaxanes constructed by selfassembly of dibenzyl
More informationSupporting Information. as the nitro source
Supporting Information Efficient ipso-nitration of arylboronic acids with iron nitrate as the nitro source Min Jiang, a,b Haijun Yang,* a,b Yong Li, a,b Zhiying Jia b and Hua Fu b a Beijing Key Laboratory
More informationNitro-Grela-type complexes containing iodides. robust and selective catalysts for olefin metathesis
Supporting Information for Nitro-Grela-type complexes containing iodides robust and selective catalysts for olefin metathesis under challenging conditions. Andrzej Tracz, 1,2 Mateusz Matczak, 1 Katarzyna
More informationSupporting Materials. Experimental Section. internal standard TMS (0 ppm). The peak patterns are indicated as follows: s, singlet; d,
CuBr-Catalyzed Efficient Alkynylation of sp 3 C-H Bonds Adjacent to a itrogen Atom Zhiping Li and Chao-Jun Li* Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec H3A
More informationSupporting Information
Supporting Information Synthesis of Pyrido-fused Quinazolinone Derivatives via Copper-catalyzed Domino Reaction Meilin Liu, Miaomiao Shu, Chaochao Yao, Guodong Yin,* Dunjia Wang, and Jinkun Huang* Hubei
More informationManganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature
Supplementary Information Manganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature Weili Si 1, Xuan Zhang 1, Shirong Lu 1, Takeshi Yasuda
More informationStereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines
Stereoselective Aza-Darzens Reactions of Tert- Butanesulfinimines: Convenient Access to Chiral Aziridines Toni Moragas Solá, a Ian Churcher, b William Lewis a and Robert A. Stockman* a Supplementary Information
More informationCu-Catalyzed Direct C6-Arylation of Indoles
Cu-Catalyzed Direct C6-Arylation of Indoles (Supporting Information) Youqing Yang, Ruirui Li, Yue Zhao, Dongbing Zhao, and Zhuangzhi Shi*, State Key Laboratory of Coordination Chemistry, Collaborative
More informationLewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines
Supporting Information for Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines Yingle Liu a, Jiawang Liu
More informationRuthenium-Catalyzed C H Oxygenation on Aryl Weinreb Amides
Supporting Information Ruthenium-Catalyzed C H xygenation on Aryl Weinreb Amides Fanzhi Yang and Lutz Ackermann* Institut für rganische und Biomolekulare Chemie Georg-August-Universität Tammannstrasse
More informationSupporting Information
Supporting Information Unconventional Passerini Reaction towards α-aminoxyamides Ajay L. Chandgude, Alexander Dömling* Department of Drug Design, University of Groningen, Antonius Deusinglaan 1, 9713 AV
More informationMasatoshi Shibuya,Takahisa Sato, Masaki Tomizawa, and Yoshiharu Iwabuchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences,
Oxoammonium ion/naclo 2 : An Expedient, Catalytic System for One-pot Oxidation of Primary Alcohols to Carboxylic Acid with Broad Substrate Applicability Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa,
More informationSupporting information for. Synthesis of phenothiazines from cyclohexanones and. 2-aminobenzenethiols under transition-metal-free conditions
Supporting information for Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions Yunfeng Liao, a Pengcheng Jiang, a Shanping Chen, a Fuhong Xiao,
More informationDirect Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source
Direct Aerobic Carbonylation of C(sp 2 )-H and C(sp 3 )-H Bonds through Ni/Cu Synergistic Catalysis with DMF as the Carbonyl Source Xuesong Wu, Yan Zhao, and Haibo Ge* Table of Contents General Information...
More informationDirect ortho-c H Functionalization of Aromatic Alcohols Masked by Acetone Oxime Ether via exo-palladacycle
Direct ortho-c H Functionalization of Aromatic Alcohols Masked by Acetone Oxime Ether via exo-palladacycle Kun Guo, Xiaolan Chen, Mingyu Guan, and Yingsheng Zhao* Key Laboratory of Organic Synthesis of
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information [Fe III (TF4DMAP)OTf] Catalysed Anti-Markovnikov Oxidation
More informationSUPPORTING INFORMATION. Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S
1 SUPPORTING INFORMATION Transition metal-promoted synthesis of 2-aryl/heteroaryl-thioquinazoline: C-S Bond formation by Chan-Lam Cross-Coupling Reaction SATYA KARUNA PULAKHANDAM a, NARESH KUMAR KATARI
More informationPyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles. Supporting Information
Pyridazine N-Oxides as Precursors of Metallocarbenes: Rhodium-Catalyzed Transannulation with Pyrroles Vinaykumar Kanchupalli, Desna Joseph and Sreenivas Katukojvala* Department of Chemistry, Indian Institute
More informationElectronic Supplementary Information
Electronic Supplementary Information A Novel and Facile Zn-mediated Intramolecular Five-membered Cyclization of β-tetraarylporphyrin Radicals from β-bromotetraarylporphyrins Dong-Mei Shen, Chao Liu, Qing-Yun
More informationCatalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds
Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon nitrogen and carbon carbon bonds Cui-Feng Yang, Jian-Yong Wang and Shi-Kai Tian* Joint Laboratory of Green
More informationOne-pot Synthesis of 1-Alkyl-1H-indazoles. Supporting Information
One-pot Synthesis of 1-Alkyl-1H-indazoles from 1,1-Dialkylhydrazones via Aryne Annulation ataliya A. Markina, Anton V. Dubrovskiy, and Richard C. Larock* Department of Chemistry, Iowa State University,
More informationPreparation of Stable Aziridinium Ions and Their Ring Openings
Supplementary Information Preparation of Stable Aziridinium Ions and Their Ring Openings Yongeun Kim a Hyun-Joon Ha*, a Sae Young Yun b and Won Koo Lee,*,b a Department of Chemistry and Protein Research
More informationSupporting Information
Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2011 Supporting Information Potassium tert-butoxide Mediated Heck-Type Cyclization/Isomerization
More informationZinc Chloride Promoted Formal Oxidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides
Supporting information for Zinc Chloride Promoted Formal xidative Coupling of Aromatic Aldehydes and Isocyanides to α- Ketoamides Marinus Bouma, Géraldine Masson* and Jieping Zhu* Institut de Chimie des
More informationSupporting Information
Supporting Information Synthesis of N-Heteropolycyclic Compounds Including Quinazolinone Skeletons by Using Friedel-Crafts Alkylation Bu Keun Oh, Eun Bi Ko, Jin Wook Han* and Chang Ho Oh* Department of
More informationph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors
ph Switchable and Fluorescent Ratiometric Squarylium Indocyanine Dyes as Extremely Alkaline Sensors Jie Li, Chendong Ji, Wantai Yang, Meizhen Yin* State Key Laboratory of Chemical Resource Engineering,
More informationA pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state
A pillar[2]arene[3]hydroquinone which can self-assemble to a molecular zipper in the solid state Mingguang Pan, Min Xue* Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China Fax:
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Supporting Information Enantioselective Cu-catalyzed 1,4-Addition of Various Grignard Reagents to Cyclohexenone using Taddol-derived Phosphine-Phosphite
More informationDivergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes
Divergent Construction of Pyrazoles via Michael Addition of N-Aryl Hydrazones to 1,2-Diaza-1,3-dienes Serena Mantenuto, Fabio Mantellini, Gianfranco Favi,* and Orazio A. Attanasi Department of Biomolecular
More informationSpecific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides
Supporting Information Specific N-Alkylation of Hydroxypyridines Achieved by a Catalyst- and Base-Free Reaction with Organohalides Bin Feng, Yang Li, Huan Li, Xu Zhang, Huamei Xie, Hongen Cao, Lei Yu,
More informationImproved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides
Albaneze-Walker et al S-1 Improved Carbonylation of Heterocyclic Chlorides and Challenging Aryl Bromides Jennifer Albaneze-Walker*, Charles Bazaral, Tanya Leavey, Peter G. Dormer, and Jerry A. Murry Department
More informationElectronic Supplementary Information
Electronic Supplementary Information ~ Experimental Procedures and Spectral/Analytical Data ~ Use of Dimethyl Carbonate as a Solvent Greatly Enhances the Biaryl Coupling of Aryl Iodides and Organoboron
More informationSupporting Information for. Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the. analysis of Glucose in Whole Blood
Supporting Information for Boronic Acid Functionalized Aza-Bodipy (azabdpba) based Fluorescence Optodes for the analysis of Glucose in Whole Blood Yueling Liu, Jingwei Zhu, Yanmei Xu, Yu Qin*, Dechen Jiang*
More informationPh 2 SO-Tf 2 O: a Powerful Promotor System in Chemoselective Glycosylations Using Thioglycosides
Ph 2 SO-Tf 2 O: a Powerful Promotor System in Chemoselective Glycosylations Using Thioglycosides Jeroen D. C. Codée, Remy E. J. N. Litjens, René den Heeten, Herman S. Overkleeft, Jacques H. van Boom, Gijsbert
More informationSupporting information
Supporting information Diversity Oriented Asymmetric Catalysis (DOAC): Stereochemically Divergent Synthesis of Thiochromanes Using an Imidazoline-aminophenol aminophenol (IAP)-Ni Catalyzed Michael/Henry
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Organocatalytic Asymmetric Sulfa-Michael Addition to α,β- Unsaturated Ketones Paolo Ricci, Armando Carlone, Giuseppe
More informationPreparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF
Supporting information Preparation of Fluorinated Tetrahydropyrans and Piperidines using a New Nucleophilic Fluorination Reagent DMPU/HF Otome E. Okoromoba, a Gerald B. Hammond, a, * Bo Xu b, * a Department
More informationSupporting Information
Supporting Information Asymmetric Catalysis of the Carbonyl-Amine Condensation: Kinetic Resolution of Primary Amines Sayantani Das, Nilanjana Majumdar, Chandra Kanta De, Dipti Sankar Kundu, Arno Döhring,
More informationElectronic Supplementary Information (ESI)
Electronic Supplementary Information (ESI) Mild and convenient one-pot synthesis of 2-amino-1,3,4-oxadiazoles promoted by trimethylsilyl isothiocyanate (TMSNCS) Dinneswara Reddy Guda, Hyeon Mo Cho, Myong
More informationCatalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water
SUPPORTING INFORMATION Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water Sunay V. Chankeshwara and Asit K. Chakraborti* National Institute of Pharmaceutical Education and Research
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Supporting Information General. NMR spectra for identification of intermediates and final compoundswere recorded
More informationSupporting Information. Palladium-catalyzed reductive cleavage of tosylated arene using isopropanol as the mild reducing agent
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2014 Supporting Information Supporting Information Palladium-catalyzed reductive cleavage
More information# Supplementary Material (ESI) for Chemical Communications # This journal is The Royal Society of Chemistry 2005
Electronic Supplementary Information for: (Z)-Selective cross-dimerization of arylacetylenes with silylacetylenes catalyzed by vinylideneruthenium complexes Hiroyuki Katayama,* Hiroshi Yari, Masaki Tanaka,
More informationIron-Catalyzed Alkylation of Alkenyl Grignard Reagents
Supporting Information for Iron-Catalyzed Alkylation of Alkenyl Grignard Reagents Gérard Cahiez,* Christophe Duplais and Alban Moyeux Laboratoire de Synthèse Organique Sélective et de Chimie Organométallique
More informationSchwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins
Electronic Supplementary Information (ESI) Schwartz s reagent-mediated regiospecific synthesis of 2,3-disubstituted indoles from isatins A. Ulikowski and B. Furman* Institute of Organic Chemistry, Polish
More informationDevelopment of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells
Supporting Information for Development of a near-infrared fluorescent probe for monitoring hydrazine in serum and living cells Sasa Zhu, Weiying Lin,* Lin Yuan State Key Laboratory of Chemo/Biosensing
More informationSupporting Information. Ruthenium(II)-Catalyzed C H Alkynylation of Weakly-Coordinating Benzoic Acids. Ruhuai Mei, Shou-Kun Zhang, and Lutz Ackermann*
Supporting Information Ruthenium(II)-Catalyzed C H Alkynylation of Weakly-Coordinating Benzoic Acids Ruhuai Mei, Shou-Kun Zhang, and Lutz Ackermann* Institut für Organische und Biomolekulare Chemie, Georg-August-Universität
More informationElectronic Supplementary Information. Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of
Electronic Supplementary Information Quinine/Selectfluor Combination Induced Asymmetric Semipinacol Rearrangement of Allylic Alcohols: An Effective and Enantioselective Approach to α Quaternary β Fluoro
More informationAn iron catalyzed regioselective oxidation of terminal alkenes to aldehydes
Electronic Supplementary Information An iron catalyzed regioselective oxidation of terminal alkenes to aldehydes Abhishek Dutta Chowdhury, Ritwika Ray and Goutam Kumar Lahiri * Department of Chemistry,
More informationSupplementary Information
Supplementary Information Ruthenium(IV) porphyrin catalyzed phosphoramidation of aldehyde with phosphoryl azide as nitrene source Wenbo Xiao, Cong-Ying Zhou and Chi-Ming Che* Department of Chemistry, State
More informationSolid Phase Peptide Synthesis (SPPS) and Solid Phase. Fragment Coupling (SPFC) Mediated by Isonitriles
Solid Phase Peptide Synthesis (SPPS) and Solid Phase Fragment Coupling (SPFC) Mediated by Isonitriles Ting Wang a and Samuel J. Danishefsky a,b,* alaboratory for Bioorganic Chemistry, Sloan- Kettering
More informationSupporting Information
Supporting Information for Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5- tetrafluorocyclohexane Mohammed Salah Ayoup 1,2, David B. Cordes 1,
More informationSupporting Information
Supporting Information A Regioselective Ring-Expansion of Isatins with In-situ Generated α-aryldiazomethanes; Direct Access to Viridicatin Alkaloids Yellaiah Tangella,, Kesari Lakshmi Manasa,, Namballa
More informationPalladium-catalyzed Decarbonylative Alkynylation of Aromatic Esters
Palladium-catalyzed Decarbonylative Alkynylation of Aromatic Esters Toshimasa Okita, 1 Kazushi Kumazawa, 2 Ryosuke Takise, 2 Kei Muto, 1 Kenichiro Itami,* 2,3 and Junichiro Yamaguchi* 1 1 Department of
More informationElectronic Supplementary Information
Efficient aerobic oxidative synthesis of 2-aryl quinazolines via benzyl C-H bond amination catalyzed by 4-hydroxy-TEMPO Bing Han,* Chao Wang, Run-Feng Han, Wei Yu,* Xiao-Yong Duan, Ran Fang and Xiu-Long
More informationSupporting Information
Supporting Information De Novo Synthesis of Polysubstituted Naphthols and Furans Using Photoredox Neutral Coupling of Alkynes with 2-Bromo-1,3-Dicarbonyl Compounds Heng Jiang, Yuanzheng Cheng, Yan Zhang,*
More informationby Donor-Acceptor Complex
Metal-Free C(sp 3 )-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex Yang Li 1+, Jing Zhang 1+, Defang Li 1,2, and Yiyun Chen 1,2 * Supplementary Information I. General Procedures...
More informationSupporting Information
Supporting Information [Cp*IrCl 2 ] 2 catalysed indirect functionalisation of alcohols: ovel strategies for the synthesis of substituted indoles Simon Whitney, Ronald Grigg *, Andrew Derrick and Ann Keep
More informationA bidirectional synthesis of spiroacetals via Rh(II)-catalysed C H insertion
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information A bidirectional synthesis of spiroacetals via Rh(II)-catalysed C H insertion
More informationRameshwar Prasad Pandit and Yong Rok Lee * School of Chemical Engineering, Yeungnam University, Gyeongsan , Korea
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Novel ne-pot Synthesis of Diverse γ,δ-unsaturated β-ketoesters by Thermal
More informationAsymmetric organocatalytic diboration of alkenes
Asymmetric organocatalytic diboration of alkenes Amadeu Bonet, a Cristina Solé, Henrik Gulyás,* Elena Fernández* a Dept. Química Física i Inorgànica, University Rovira i Virgili, C/Marcel lí Domingo s/n,
More information1,5-Electrocyclization of conjugated azomethine ylides derived from 3-formyl chromene and N-alkyl amino acids/esters
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 7 Supporting Information for,5-electrocyclization of conjugated azomethine ylides
More informationGold(I)-Catalysed Dehydrative Formation of Ethers From Benzylic Alcohols and Phenols
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 205 Gold(I)-Catalysed Dehydrative ormation of Ethers rom Benzylic Alcohols and enols Richard
More informationSupporting Information
Supporting Information Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles Xiaoqiang Lei, Mohan Gao, Yefeng Tang*,,, E-mail: yefengtang@tsinghua.edu.cn
More informationSupport Information. Table of contents. Experimental procedures. S2. Spectroscopic data... S2-S23. Photophysical properties..
Support Information Regioselective 2,6-dihalogenation of BODIPYs in 1,1,1,3,3,3-hexafluoro-2-propanol and preparation of novel meso-alkyl polymeric BODIPY dyes Liang Wang a, Jian-Wei Wang a, Ai-jun Cui
More informationSupporting Information
Zinc-Mediated Addition of Diethyl Bromomalonate to Alkynes for the Cascade Reaction towards Polysubstituted Pyranones and Tetracarbonyl Derivatives Anne Miersch, Klaus Harms, and Gerhard Hilt* Fachbereich
More informationSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 6951 Weinheim, 2008 COMMUNICATION Copper or Iron Catalysed Arylation of Phenols from respectively Aryl Chlorides and Aryl Iodides Ning
More informationEur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007 ISSN X SUPPORTING INFORMATION
Eur. J. Org. Chem. 2007 WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 ISSN 1434 193X SUPPORTING INFORMATION Title: Effect of Varying the Anionic Component of a Copper(I) Catalyst on Homologation
More informationAn Unusual Glycosylation Product from a Partially Protected Fucosyl Donor. under Silver Triflate activation conditions. Supporting information
An Unusual Glycosylation Product from a Partially Protected Fucosyl Donor under Silver Triflate activation conditions Robin Daly a and Eoin M. Scanlan* a e-mail: eoin.scanlan@tcd.ie a Trinity Biomedical
More informationAllenylphosphine oxides as simple scaffolds for. phosphinoylindoles and phosphinoylisocoumarins
Supporting Information for Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins G. Gangadhararao, Ramesh Kotikalapudi, M. Nagarjuna Reddy and K. C. Kumara Swamy*
More informationElectronic Supporting Information
Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers. This journal is the Partner Organisations 2018 Electronic Supporting Information Tetraphenylpyrazine-based luminogens with full-colour
More informationNHC-catalyzed cleavage of vicinal diketones and. triketones followed by insertion of enones and
Supporting Information for NHC-catalyzed cleavage of vicinal diketones and triketones followed by insertion of enones and ynones Ken Takaki*, Makoto Hino, Akira Ohno, Kimihiro Komeyama, Hiroto Yoshida
More informationCopyright Wiley-VCH Verlag GmbH, D Weinheim, Angew. Chem
Copyright Wiley-VCH Verlag GmbH, D-69451 Weinheim, 2000. Angew. Chem. 2000. Supporting Information for Salen as Chiral Activator : Anti vs Syn Switchable Diastereoselection in the Enantioselective Addition
More informationSupplemental Material
Supplemental Material General Methods Unless otherwise indicated, all anhydrous solvents were commercially obtained and stored under nitrogen. Reactions were performed under an atmosphere of dry nitrogen
More informationSelf-organization of dipyridylcalix[4]pyrrole into a supramolecular cage for dicarboxylates
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information Self-organization of dipyridylcalix[4]pyrrole into a supramolecular
More informationSupporting Information. for. Synthesis of dye/fluorescent functionalized. dendrons based on cyclotriphosphazene
Supporting Information for Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene Aurélien Hameau 1,2, Sabine Fuchs 1,2, Régis Laurent 1,2, Jean-Pierre Majoral* 1,2 and Anne-Marie
More informationEnantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction
Enantioselective synthesis of anti- and syn-β-hydroxy-α-phenyl carboxylates via boron-mediated asymmetric aldol reaction P. Veeraraghavan Ramachandran* and Prem B. Chanda Department of Chemistry, Purdue
More informationAccessory Publication
10.1071/CH09088_AC CSIRO 2009 Accessory Publication: Australian Journal of Chemistry, 2009, 62(8), 790 793 Thermally Responsive Elastomeric Supramolecular Polymers Featuring Flexible Aliphatic Hydrogen
More informationSUPPLEMENTARY MATERIAL
SUPPLEMENTARY MATERIAL Chemical constituents from Agrimonia pilosa Ledeb. and their chemotaxonomic significance Wei-jie Liu, Xue-qian Hou, Hao Chen, Jing-yu Liang*, Jian-bo Sun** Department of Natural
More informationBase-promoted acetal formation employing aryl salicylates
Base-promoted acetal formation employing aryl salicylates Pinmanee Boontheung, Patrick Perlmutter*, and Evaloni Puniani School of Chemistry, Monash University, PO Box 23, Victoria 3800 Australia E-mail:
More informationIodide as an Activating Agent for Acid Chlorides in Acylation Reactions.
Iodide as an Activating Agent for Acid Chlorides in Acylation Reactions. Russell J. Wakeham a, James E. Taylor a, Steven D. Bull a, James A. Morris b and Jonathan M. J. Williams a a Department of Chemistry,
More informationEthyl 2-hydroxy-4-methyl-1-((prop-2-yn-1-yloxy)methyl)cyclohex-3-enecarboxylate (16):
General methods: 1 H NMR and 13 C NMR spectra were recorded in CDCl 3 or CDCl3 and CCl 4 as solvent on 300 MHz or 500 MHz spectrometer at ambient temperature. The coupling constant J is given in Hz. The
More informationA multicomponent CuAAC click approach. to a library of hybrid polydentate 2-pyridyl- the generation of metallosupramolecular. architectures.
Supporting information A multicomponent CuAAC click approach to a library of hybrid polydentate 2-pyridyl- 1,2,3-triazole ligands: New building blocks for the generation of metallosupramolecular architectures.
More informationAll chemicals were obtained from Aldrich, Acros, Fisher, or Fluka and were used without
Supplemental Data Alexander et al. Experimental Procedures General Methods for Inhibitor Synthesis All chemicals were obtained from Aldrich, Acros, Fisher, or Fluka and were used without further purification,
More information