Supporting Information

Μέγεθος: px
Εμφάνιση ξεκινά από τη σελίδα:

Download "Supporting Information"

Transcript

1 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 of omoalkynes with -Allylamines Jia Zheng, Liangbin Huang, Zun Li, Wanqing Wu, Jianxiao Li, Huanfeng Jiang* School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou , P. R. China Supporting Information A. General methods S2 B. General procedure for the synthesis of pyrrole derivatives... S2 C. Reactions between other haloalkynes and -allylamines... S2 D. Analytical data for pyrrole derivatives S2 E. MR Spectra.. S13 F. Studies on the stereochemistry of 3fa and 5a.. S45 G. X-ray Crystallographic Analysis of S47

2 A. General methods 1 H and 13 C MR spectra were recorded on a 400 MHz spectrometer using CDCl 3 as solvent and TMS as an internal standard. Mass spectra were obtained with gas chromatography mass spectrometer. IR spectra were obtained either as potassium bromide pellets or as liquid films between two potassium bromide pellets with a spectrometer. GC MS was obtained using electron ionization. HRMS was obtained with a LCMS-IT-TOF mass spectrometer. B. General procedure for the synthesis of pyrrole derivatives -Allylamine (0.2 mmol), bromoalkynes (0.2 mmol), PdCl 2 (10 mol %) and BQ (2 equiv) were added to 2 ml toluene/dmso (5/1). The mixture was stirred under air at 110 o C for the desired reaction time. After that, water was added and extracted with ethyl acetate twice. The combined organic phase was dried over a 2 SO 4 and concentrated. The residue was eventually purified by flash column chromatography on silica gel with petroleum ether/ethyl acetate as the eluent to afford the corresponding pyrroles. C. Reactions between other haloalkynes and -allylamines Ph 1r I Tol H 1a H standard conditions Ph 11 < 20% Ph Tol Me I Ph 3ra not detected Ph 1s Cl Tol H 1a H standard conditions Tol Me Cl Ph 3sa trace D. Analytical data for pyrrole derivatives 3-omo-4-methyl-2-phenyl-1-(p-tolyl)-1H-pyrrole (3aa)

3 White solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.15 (dd, J = 12.6, 5.9 Hz, 5H), 6.96 (d, J = 7.9 Hz, 2H), 6.84 (d, J = 7.9 Hz, 2H), 6.66 (s, 1H), 2.22 (s, 3H), 2.08 (s, 3H). 13 C MR (101 MHz, CDCl 3 ) δ 137.8, 136.3, 131.3, 130.4, 130.3, 129.5, 127.9, 127.1, 125.1, 120.6, 119.5, 100.9, 20.9, 11.3 ppm. MS (EI, 70 ev) m/z: 91, 128, 231, 246, 325. HRMS (ESI) m/z: calcd for C 18 H 17 [M+H] +, ; found, IR (K): 2922, 2854, 1670, 1608, 1514, 1445, 1356, 1042, 695 cm omo-1-(4-methoxyphenyl)-4-methyl-2-phenyl-1H-pyrrole (3ab) O Red solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.14 (dd, J = 11.7, 5.9 Hz, 5H), 6.88 (d, J = 8.4 Hz, 2H), 6.68 (d, J = 8.5 Hz, 2H), 6.63 (s, 1H), 3.67 (s, 3H), 2.07 (s, 3H). 13 C MR (101 MHz, CDCl 3 ) δ 158.1, 133.5, 131.3, 130.6, 130.4, 127.9, 127.1, 126.6, 120.7, 119.3, 114.1, 100.6, 55.4, 11.3 ppm. MS (EI, 70 ev) m/z: 77, 128, 231, 262, 341. HRMS (ESI) m/z: calcd for C 18 H 17 O [M+H] +, ; found, IR (K): 2924, 2850, 1605, 1512, 1463, 1248, 1039, 833 cm omo-4-methyl-1,2-diphenyl-1H-pyrrole (3ac) White solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 8H), 7.07 (d, J = 7.4 Hz, 2H), 6.81 (s, 1H), 2.20 (s, 3H). 13 C MR (101 MHz, CDCl 3 ) δ 140.3, 131.2, 130.4, 130.3, 128.9, 127.9, 127.2, 126.5, 125.3, 120.5, 119.7, 101.3, ppm; MS (EI, 70 ev) m/z: 77, 128, 232, 311. HRMS (ESI) m/z: calcd for C 17 H 15 [M+H] +, ; found, IR (K): 3063, 2922, 1851, 1598, 1498, 1355, 757, 697 cm omo-1-(4-fluorophenyl)-4-methyl-2-phenyl-1H-pyrrole (3ad) F Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.14 (m, 5H), (m, 2H), 6.84 (t, J = 8.3 Hz, 2H), 6.63 (s, 1H), 2.07 (s, 3H). 13 C MR (100 MHz,

4 CDCl 3 ) δ (d, J = 245 Hz), (d, J = 3 Hz), 131.0, 130.7, 130.4, 130.1, 128.0, 127.3, (d, J = 8 Hz), 120.6, 119.8, (d, J = 23 Hz), 101.2, 11.3 ppm; MS (EI, 70 ev) m/z: 95, 125, 250, 329. HRMS (ESI) m/z: calcd for C 17 H 14 F [M+H] +, ; found, IR (K): 2924, 2853, 1603, 1510, 1465, 1356, 1225, 839 cm omo-1-(4-chlorophenyl)-4-methyl-2-phenyl-1H-pyrrole (3ae) Cl Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 7H), 6.87 (d, J = 8.2 Hz, 2H), 6.64 (s, 1H), 2.07 (s, 3H). 13 C MR (101 MHz, CDCl 3 ) δ 138.8, 132.2, 130.9, 130.5, 130.4, 129.1, 128.1, 127.4, 126.4, 120.3, 120.2, 101.8, 11.3 ppm. MS (EI, 70 ev) m/z: 115, 128, 231, 266, 347. HRMS (ESI) m/z: calcd for C 17 H 14 ClF [M+H] +, ; found, IR (K): 3064, 2924, 2852, 1652, 1601, 1495, 1354, 1093, 1043, 832 cm omo-1-(4-isopropylphenyl)-4-methyl-2-phenyl-1H-pyrrole (3af) Yellow oil. 1 H MR (400 MHz, CDCl 3 ) δ 7.23 (d, J = 11.1 Hz, 5H), 7.09 (d, J = 7.6 Hz, 2H), 6.94 (d, J = 7.7 Hz, 2H), 6.74 (s, 1H), (m, 1H), 2.15 (s, 3H), 1.21 (d, J = 6.7 Hz, 6H). 13 C MR (100 MHz, CDCl 3 ) δ 147.2, 138.0, 131.3, 130.4, 130.3, 127.8, 127.1, 126.9, 125.1, 120.6, 119.4, 100.9, 33.58, 23.89, ppm; MS (EI, 70 ev) m/z: 128, 259, 231, 274, 353. HRMS (ESI) m/z: calcd for C 20 H 21 [M+H] +, ; found, IR (K): 2961, 2927, 2868, 1688, 1514, 1452, 1370, 1023, 705 cm omo-4-methyl-2-phenyl-1-(m-tolyl)-1H-pyrrole (3ag) White solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 5H), 7.13 (t, J = 7.7 Hz, 1H), 7.03 (d, J = 7.5 Hz, 1H), 6.93 (s, 1H), 6.80 (d, J = 8.5 Hz, 2H), 2.29

5 (s, 3H), 2.19 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 140.2, 138.9, 131.3, 130.4, 130.3, 128.6, 127.8, 127.2, 127.1, 125.8, 122.5, 120.5, 119.5, 101.1, 21.3, 11.3 ppm; MS (EI, 70 ev) m/z: 91, 129, 231, 246, 325. HRMS (ESI) m/z: calcd for C 18 H 17 [M+H] +, ; found, IR (K): 3064, 2924, 2854, 1647, 1603, 1496, 1460, 1389, 1355, 1043, 766, 696 cm omo-4-methyl-2-phenyl-1-(o-tolyl)-1H-pyrrole (3ah) White solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 9H), 6.49 (s, 1H), 2.08 (s, 3H), 1.82 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 139.6, 135.4, 131.5, 131.2, 130.7, 129.8, 128.3, 128.0, 127.8, 126.9, 126.4, 120.8, 119.3, 99.6, 17.6, 11.4 ppm; MS (EI, 70 ev) m/z: 91, 129, 231, 246, 325. HRMS (ESI) m/z: calcd for C 18 H 17 [M+H] +, ; found, IR (K): 3064, 2923, 2853, 1645, 1604, 1496, 1462, 1389, 1355, 1043, 766, 696 cm ([1,1'-Biphenyl]-2-yl)-3-bromo-4-methyl-2-phenyl-1H-pyrrole (3ai) Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 3H), 7.14 (d, J = 6.3 Hz, 1H), 7.08 (d, J = 7.2 Hz, 1H), 7.01 (t, J = 7.4 Hz, 2H), 6.95 (d, J = 7.0 Hz, 1H), 6.89 (t, J = 7.3 Hz, 2H), 6.61 (s, 1H), 6.56 (d, J = 7.5 Hz, 2H), 6.49 (d, J = 7.5 Hz, 2H), 2.05 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) 138.7, 138.2, 138.0, 131.4, 130.9, 130.8, 129.4, 128.1, 128.0, 127.9, 127.3, 127.0, 126.4, 120.7, 119.7, 99.9, 11.4.ppm; MS (EI, 70 ev) m/z: 145, 231, 307, 387. HRMS (ESI) m/z: calcd for C 23 H 18 a [M+H] +, ; found, IR (K): 3610, 2923, 2853, 1602, 1482, 1437, 1354, 1045, 766, 738, 696 cm (Benzo[d][1,3]dioxol-5-yl)-3-bromo-4-methyl-2-phenyl-1H-pyrrole (3aj) O O

6 Yellow oil. 1 H MR (400 MHz, CDCl 3 ) δ (m, 6H), 6.62 (s, 1H), 6.59 (d, J = 8.7 Hz, 1H), 6.46 (s, 2H), 5.87 (s, 2H), 2.07 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 147.7, 146.3, 134.6, 131.1, 130.6, 130.3, 127.9, 127.2, 120.8, 119.4, 118.9, 107.9, 107.1, 101.6, 100.7, ppm; MS (EI, 70 ev) m/z: 108, 218, 246, 276, 355. HRMS (ESI) m/z: calcd for C 18 H 14 ao 2 [M+H] +, ; found, IR (K): 2922, 2853, 1692, 1494, 1452, 1243, 1038 cm omo-4-ethyl-2-phenyl-1-(p-tolyl)-1H-pyrrole (3ak) Red solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 5H), 7.03 (d, J = 7.9 Hz, 2H), 6.92 (d, J = 7.9 Hz, 2H), 6.71 (s, 1H), 2.56 (q, J = 7.4 Hz, 2H), 2.29 (s, 3H), 1.28 (t, J = 7.5 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 137.9, 136.3, , 130.5, 130.4, 129.5, 127.9, 127.1, 126.0, 125.1, 119.7, 99.9, 20.9, 19.6, ppm; MS (EI, 70 ev) m/z: 91, 115, 128, 202, 244, 341. HRMS (ESI) m/z: calcd for C 19 H 19 [M+H] +, ; found, IR (K): 2964, 2924, 2858, 1656, 1608, 1514, 1463, 1375, 1069, 821, 700 cm omo-1-(4-bromophenyl)-4-ethyl-2-phenyl-1H-pyrrole (3al) Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.29 (d, J = 7.9 Hz, 2H), (m, 3H), 7.12 (d, J = 7.3 Hz, 2H), 6.84 (d, J = 7.9 Hz, 2H), 6.63 (s, 1H), 2.48 (q, J = 7.4 Hz, 2H), 1.20 (t, J = 7.0 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 139.4, 132.1, 130.9, 130.5, 130.4, 128.1, 127.4, 126.8, 126.7, 119.9, 119.4, 100.9, 19.6, ppm; MS (EI, 70 ev) m/z: 115, 128, 155, 230, 405. HRMS (ESI) m/z: calcd for C 18 H 16 2 [M+H] +, ; found, IR (K): 2965, 2926, 2854, 1694, 1596, 1491, 1370, 1067, 828, 754, 699 cm omo-1-(3,5-dimethylphenyl)-4-ethyl-2-phenyl-1H-pyrrole (3am)

7 Red oil. 1 H MR (400 MHz, CDCl 3 ) δ (m, 5H), 6.82 (s, 1H), 6.72 (s, 1H), 6.65 (s, 2H), 2.56 (q, J = 7.1 Hz, 2H), 2.19 (s, 6H), 1.28 (d, J = 7.4 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 140.2, 138.6, 131.3, 130.4, 130.3, 128.1, 127.8, 127.1, 125.9, 123.0, 119.6, 99.9, 21.1, 19.6, ppm. MS (EI, 70 ev) m/z: 77, 128, 259, 353. HRMS (ESI) m/z: calcd for C 20 H 20 a [M+H] +, ; found, IR (K): 2965, 2925, 2855, 1686, 1602, 1458, 1369, 1267, 757 cm omo-4-isopropyl-2-phenyl-1-(p-tolyl)-1H-pyrrole (3an) Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 5H), 6.96 (d, J = 7.7 Hz, 2H), 6.85 (d, J = 7.7 Hz, 2H), 6.62 (s, 1H), (m, 1H), 2.22 (s, 3H), 1.22 (d, J = 6.8 Hz, 6H). 13 C MR (100 MHz, CDCl 3 ) δ 138.0, 136.2, 131.3, 130.9, 130.5, 129.5, 127.8, 127.1, 125.1, 118.5, 99.4, 26.3, 23.1, ppm; MS (EI, 70 ev) m/z: 91, 202, 340, 355. HRMS (ESI) m/z: calcd for C 20 H 21 [M+H] +, ; found, IR (K): 2958, 2923, 2853, 1602, 1515, 1462, 1376, 821, 764, 697 cm Benzyl-3-bromo-2-phenyl-1-(p-tolyl)-1H-pyrrole (3ao) Ph Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 4H), (m, 6H), 7.01 (d, J = 7.8 Hz, 2H), 6.89 (d, J = 7.9 Hz, 2H), 6.54 (s, 1H), 3.89 (s, 2H), 2.28 (s, 3H).. 13 C MR (100 MHz, CDCl 3 ) δ 140.5, 137.8, 136.4, 131.1, 130.6, 130.4, 129.5, 128.9, 128.4, 127.9, 127.2, , 125.1, 123.7, 121.2, 100.1, 32.7, 20.9 ppm; MS (EI, 70 ev) m/z: 91, 202, 322, 403. HRMS (ESI) m/z: calcd for C 24 H 20 a [M+H] +, ; found, IR (K): 3029, 2919, 2850, 1605, 1514, 1463, 1368, 698 cm omo-4-methyl-1,2-di-p-tolyl-1H-pyrrole (3ba)

8 Yellow oil. 1 H MR (400 MHz, CDCl 3 ) δ (m, 6H), 6.94 (d, J = 8.0 Hz, 2H), 6.74 (s, 1H), 2.32 (s, 6H), 2.17 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 137.9, 136.9, 136.2, 130.5, 130.2, 129.5, 128.7, 128.4, 125.1, 120.3, 119.4, 100.7, 21.3, 20.9, 11.3 ppm; MS (EI, 70 ev) m/z: 91, 128, 260, 339. HRMS (ESI) m/z: calcd for C 19 H 18 a [M+H] +, ; found, IR (K): 3030, 2922, 2857, 1695, 1611, 1514, 1356, 1042, 820 cm -1 3-omo-2-(4-ethylphenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3ca) Yellow oil. 1 H MR (400 MHz, CDCl 3 ) δ (m, 6H), 6.95 (d, J = 7.8 Hz, 2H), 6.75 (s, 1H), 2.65 (q, J = 7.6 Hz, 2H), 2.34 (s, 3H), 2.18 (s, 3H), 1.25 (t, J = 7.6 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 143.0, 137.9, 136.2, 130.5, 130.2, 129.5, 128.5, 127.4, 125.1, 120.3, 119.4, 100.7, 28.6, 20.9, 15.1, 11.3 ppm; MS (EI, 70 ev) m/z: 91, 128, 274, 353. HRMS (ESI) m/z: calcd for C 20 H 20 a [M+H] +, ; found, IR (K): 3030, 2965, 2926, 1687, 1611, 1515, 1457, 1357, 1043, 828 cm omo-2-(4-ethoxyphenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3da) O White solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.03 (d, J = 7.8 Hz, 2H), 6.96 (d, J = 7.5 Hz, 2H), 6.84 (d, J = 7.4 Hz, 2H), 6.70 (d, J = 7.6 Hz, 2H), 6.63 (s, 1H), 3.92 (q, J = 6.5 Hz, 2H), 2.22 (s, 3H), 2.06 (s, 3H), 1.31 (t, J = 6.7 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 158.1, 137.9, 136.2, 131.6, 130.4, 129.5, 125.1, 123.6, 119.9, 119.2, 113.9, 100.5, 63.3, 20.9, 14.9, 11.3 ppm; MS (EI, 70 ev) m/z: 91, 115,

9 262, 290, 342, 269. HRMS (ESI) m/z: calcd for C 20 H 21 O [M+H] +, ; found, IR (K): 3036, 2978, 2925, 1693, 1610, 1518, 1475, 1392, 1245, 1044, 827 cm omo-2-(4-fluorophenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3ea) F Yellow oil. 1 H MR (400 MHz, CDCl 3 ) δ 7.09 (dd, J = 7.4, 5.9 Hz, 2H), 6.97 (d, J = 7.8 Hz, 2H), 6.84 (dd, J = 20.4, 8.2 Hz, 4H), 6.64 (s, 1H), 2.23 (s, 3H), 2.06 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ (d, J = 245 Hz), 137.7, 136.5, (d, J = 8.1 Hz), 129.6, 129.5, 127.4(d, J = 3 Hz), 125.2, 120.6, 119.4, 115.0(d, J = 22 Hz), 114.9, 100.9, 20.9, 11.2 ppm; MS (EI, 70 ev) m/z: 91, 146, 264, 343. HRMS (ESI) m/z: calcd for C 18 H 16 F [M+H] +, ; found, IR (K): 2924, 2855, 1691, 1603, 1513, 1357, 1228, 835 cm omo-2-(4-chlorophenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3fa) Cl Orange solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.23 (d, J = 8.0 Hz, 2H), 7.15 (d, J = 8.1 Hz, 2H), 7.08 (d, J = 7.9 Hz, 2H), 6.92 (d, J = 7.8 Hz, 2H), 6.75 (s, 1H), 2.33 (s, 3H), 2.15 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 137.6, 136.6, 133.0, 131.5, 129.8, 129.7, 129.1, 128.2, 125.2, 120.9, 119.7, 101.2, 20.9, 11.3 ppm; MS (EI, 70 ev) m/z: 91, 122, 163, 245, 280, 361. HRMS (ESI) m/z: calcd for C 18 H 15 Cla [M+H] +, ; found, IR (K): 2923, 2856, 1653, 1514, 1464, 1407, 1356, 1092, 827 cm omo-2-(4-bromophenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3ga)

10 Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.38 (d, J = 7.9 Hz, 2H), 7.08 (d, J = 8.0 Hz, 4H), 6.91 (d, J = 7.6 Hz, 2H), 6.74 (s, 1H), 2.33 (s, 3H), 2.15 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 137.6, 136.7, 131.8, 131.2, 130.3, 129.7, 129.2, 125.2, 121.3, 121.0, 119.7, , 20.9, 11.2 ppm; MS (EI, 70 ev) m/z: 91, 122, 245, 324, 405. HRMS (ESI) m/z: calcd for C 18 H 16 2 [M+H] +, ; found, IR (K): 2923, 2853, 1652, 1613, 1513, 1462, 1358, 824 cm omo-2-(4-(4-ethylcyclohexyl)phenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3ha) Yellow oil. 1 H MR (400 MHz, CDCl 3 ) δ 7.02 (q, J = 7.9 Hz, 4H), 6.95 (d, J = 7.8 Hz, 2H), 6.83 (d, J = 7.8 Hz, 2H), 6.63 (s, 1H), 2.34 (t, J = 12.1 Hz, 1H), 2.22 (s, 3H), 2.06 (s, 3H), 1.78 (d, J = 11.6 Hz, 4H), 1.33 (dd, J = 22.8, 12.4 Hz, 2H), (m, 3H), 0.96 (dd, J = 18.9, 8.4 Hz, 2H), 0.83 (d, J = 7.1 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 146.7, 137.9, 136.1, 130.6, 130.1, 129.5, 128.6, 126.3, 125.1, 120.3, 119.4, 100.7, 44.3, 39.1, 34.2, 33.2, 30.0, 20.9, 11.5, 11.3 ppm; MS (EI, 70 ev) m/z: 128, 203, 293, 372. HRMS (ESI) m/z: calcd for C 26 H 30 a [M+H] +, ; found, IR (K): 2922, 2851, 1694, 1614, 1515, 1454, 1357, 825 cm omo-4-methyl-2-(m-tolyl)-1-(p-tolyl)-1H-pyrrole (3ia) Yellow oil. 1 H MR (400 MHz, CDCl 3 ) δ (m, 2H), 6.94 (d, J = 6.9 Hz, 3H), 6.84 (t, J = 10.9 Hz, 3H), 6.63 (s, 1H), 2.20 (s, 3H), 2.17 (s, 3H), 2.06 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 137.9, 137.4, 136.2, 131.3, 131.1, 130.6, 129.5, 127.9, 127.8, 127.5, 125.1, 120.4, 119.4, 100.9, 21.4, 20.9, 11.3 ppm; MS (EI, 70 ev) m/z: 91, 115, 245, 260, 341. HRMS (ESI) m/z: calcd for C 19 H 18 a [M+H] +, ; found, IR (K): 3034, 2922, 2857, 1690, 1609, 1514, 1454, 1357, 1043 cm omo-2-(3-chlorophenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3ja)

11 Cl Red oil. 1 H MR (400 MHz, CDCl 3 ) δ 7.27 (s, 3H), 7.16 (dd, J = 18.7, 7.9 Hz, 2H), 7.07 (d, J = 7.7 Hz, 2H), 7.01 (d, J = 7.4 Hz, 1H), 6.91 (d, J = 7.6 Hz, 2H), 6.74 (s, 1H), 2.32 (s, 3H), 2.14 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 137.5, 136.7, 133.7, 133.1, 130.2, 129.7, 129.1, 128.9, 128.5, 127.2, 125.2, 121.2, 119.7, 101.5, 20.9, 11.2 ppm; MS (EI, 70 ev) m/z: 91, 115, 163, 245, 280, 361. HRMS (ESI) m/z: calcd for C 18 H 16 Cl [M+H] +, ; found, IR (K): 2924, 2854, 1693, 1600, 1514, 1461, 1356, 1044 cm omo-2-(2-fluorophenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3ka) F Yellow solid. M.p.: ºC 1 H MR (400 MHz, CDCl 3 ) δ (m, 2H), 7.13 (t, J = 7.5 Hz, 1H), 7.06 (d, J = 7.7 Hz, 2H), 6.99 (dd, J = 17.9, 8.4 Hz, 3H), 6.82 (s, 1H), 2.32 (s, 3H), 2.19 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ (d, J = 247 Hz), 158.8, 137.8, 136.4, (d, J = 2.6 Hz), (d, J = 8.1 Hz, ), 129.5, 124.9, 124.4, 124.3, (d, J = 3.6 Hz,), 120.6, 119.8, 119.7, (d, J = 16 Hz), (d, J = 22.0 Hz,), (s, 5H), (s, 4H), (s, 3H). ppm; MS (EI, 70 ev) m/z: 91, 146, 249, 264, 343. HRMS (ESI) m/z: calcd for C 18 H 16 F [M+H] +, ; found, IR (K): 2924, 2854, 1692, 1611, 1515, 1455, 1358, 1043, 756 cm omo-2-(2,4-dimethylphenyl)-4-methyl-1-(p-tolyl)-1H-pyrrole (3la) Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.07 (d, J = 8.0 Hz, 1H), 7.00 (d, J = 7.7 Hz, 2H), 6.96 (s, 2H), 6.89 (d, J = 7.7 Hz, 2H), 6.77 (s, 1H), 2.31 (s, 3H), 2.28 (s, 3H), 2.16 (s, 3H), 1.98 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 138.2, 138.1, 138.0, 135.8, 131.8, 130.7, 130.5, 129.4, 128.5, 126.2, 124.1, 119.0, 118.9, 101.5, 21.3, 20.9, 19.8, 11.3 ppm; MS (EI, 70 ev) m/z: 91, 274, 355. HRMS

12 (ESI) m/z: calcd for C 20 H 21 [M+H] +, ; found, IR (K): 2922, 2856, 1612, 1515, 1448, 1393, 1354, 1043, 821 cm bromo-4-methyl-2-(thiophen-3-yl)-1-(p-tolyl)-1H-pyrrole (3ma) S Orange solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.15 (s, 2H), 7.08 (d, J = 7.8 Hz, 2H), 6.96 (d, J = 7.8 Hz, 2H), 6.85 (d, J = 4.4 Hz, 1H), 6.69 (s, 1H), 2.33 (s, 3H), 2.13 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 137.9, 136.7, 131.3, 129.6, 128.7, 126.3, 125.3, 124.3, 120.4, 119.5, 100.8, 21.0, 11.3 ppm; MS (EI, 70 ev) m/z: 91, 118, 237, 252, 333. HRMS (ESI) m/z: calcd for C 16 H 14 as [M+H] +, ; found, IR (K): 2922, 2853, 1658, 1514, 1414, 1355, 1044, 784 cm -1. Ethyl 4-methyl-2-phenyl-1-(p-tolyl)-1H-pyrrole-3-carboxylate (5a) COOEt Yellow solid. M.p.: 97-98ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 5H), 6.91 (d, J = 7.9 Hz, 2H), 6.80 (d, J = 7.9 Hz, 2H), 6.57 (s, 1H), 4.03 (q, J = 7.1 Hz, 2H), 2.27 (s, 3H), 2.18 (s, 3H), 1.00 (t, J = 7.1 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 165.6, 138.2, 137.0, 136.8, 132.3, 131.2, 129.4, 127.5, 127.4, 125.8, 121.8, 121.6, 113.8, 59.3, 20.9, 14.1, 12.3 ppm; MS (EI, 70 ev) m/z: 91, 128, 274, 319. HRMS (ESI) m/z: calcd for C 21 H 21 ao 2 [M+H] +, ; found, IR (K): 2977, 2923, 2854, 1699, 1604, 1516, 1477, 1410, 1256, 1086 cm -1. Ethyl 4-methyl-2-(naphthalen-2-yl)-1-(p-tolyl)-1H-pyrrole-3-carboxylate (5b) COOEt Yellow solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.82 (d, J = 7.6 Hz, 1H), 7.73 (d, J = 7.1 Hz, 3H), 7.47 (dd, J = 11.7, 6.0 Hz, 2H), 7.35 (d, J = 8.5 Hz, 1H), 6.99 (q, J = 8.2 Hz, 4H), 6.76 (s, 1H), 4.14 (q, J = 7.0 Hz, 2H), 2.45 (s, 3H), 2.27 (s, 3H), 1.06 (t, J = 7.1 Hz, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 165.6, 137.9, 137.0,

13 136.8, 132.7, 132.6, 130.6, 129.8, 129.5, 128.9, 128.2, 127.6, 126.7, 126.1, 125.8, 125.7, 122.1, 121.8, 114.2, 59.3, 20.9, 14.1, ppm; MS (EI, 70 ev) m/z: 91, 178, 296, 324, 369. HRMS (ESI) m/z: calcd for C 25 H 24 O 2 [M+H] +, ; found, IR (K): 2980, 2923, 2851, 1699, 1515, 1464, 1411, 1256, 1085 cm-1. 4-Methyl-2-phenyl-3-(1-phenylvinyl)-1-(p-tolyl)-1H-pyrrole (9) White solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ 7.48 (d, J = 7.4 Hz, 2H), (m, 4H), (m, 7H), 7.02 (d, J = 7.9 Hz, 2H), 6.78 (s, 1H), 5.66 (s, 1H), 5.07 (s, 1H), 2.35 (s, 3H), 1.91 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 142.9, 141.8, 138.1, 135.7, 132.6, 131.4, 130.3, 129.4, 128.1, 127.6, 127.2, 126.8, 126.2, 125.4, 124.6, 121.0, 119.3, 116.6, 20.9, 10.8 ppm; MS (EI, 70 ev) m/z: 91, 215, 272, 334, 348. HRMS (ESI) m/z: calcd for C 26 H 24 [M+H] +, ; found, IR (K): 3057, 2923, 2853, 1695, 1572, 1515, 1400, 698 cm Methyl-2,3-diphenyl-1-(p-tolyl)-1H-pyrrole (10) White solid. M.p.: ºC. 1 H MR (400 MHz, CDCl 3 ) δ (m, 2H), (m, 3H), (m,, 5H), (m, 4H), 6.80 (s, 1H), 2.31 (s, 3H), 2.16 (s, 3H). 13 C MR (100 MHz, CDCl 3 ) δ 137.9, 136.1, 135.8, 132.4, 130.8, , 130.4, 129.4, 127.8, 127.7, 126.3, 125.6, 125.5, 124.6, 121.5, 118.5, 20.9, 11.0 ppm; MS (EI, 70 ev) m/z: 91, 145, 191, 205, 323. HRMS (ESI) m/z: calcd for C 24 H 22 [M+H] +, ; found, IR (K): 3058, 2922, 2853, 1601, 1516, 1369, 698 cm -1.

14 E. MR Spectra 3aa- 1 H 3aa- 13 C

15 3ab- 1 H 3ab- 13 C

16 3ac- 1 H 3ac- 13 C

17 3ad- 1 H 3ad- 13 C

18 3ae- 1 H 3ae- 13 C

19 3af- 1 H 3af- 13 C

20 3ag- 1 H 3ag- 13 C

21 3ah- 1 H 3ah- 13 C

22 3ai- 1 H 3ai- 13 C

23 3aj- 1 H 3aj- 13 C

24 3ak- 1 H 3ak- 13 C

25 3al- 1 H 3al- 13 C

26 3am- 1 H 3am- 13 C

27 3an- 1 H 3an- 13 C

28 3ao- 1 H 3ao- 13 C

29 3ba- 1 H 3ba- 13 C

30 3ca- 1 H 3ca- 13 C

31 3da- 1 H 3da- 13 C

32 3ea- 1 H 3ea- 13 C

33 3fa- 1 H 3fa- 13 C

34 3ga- 1 H 3ga- 13 C

35 3ha- 1 H 3ha- 13 C

36 3ia- 1 H 3ia- 13 C

37 3ja- 1 H 3ja- 13 C

38 3ka- 1 H 3ka- 13 C

39 3la- 1 H 3la- 13 C

40 3ma- 1 H 3ma- 13 C

41 5a- 1 H 5a- 13 C

42 5b- 1 H 5b- 13 C

43 9-1 H 9-13 C

44 10-1 H C

45 F. Studies on the stereochemistry of 3fa and 5a

46

47 G. X-ray Crystallographic Analysis of 9 9 Summary of Data CCDC Formula: C26 H23 1 Unit Cell Parameters: a (3) b (15) c (4) P21/n

Copper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones

Copper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation

Διαβάστε περισσότερα

Metal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides

Metal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information for Metal-free Oxidative Coupling of Amines with Sodium Sulfinates:

Διαβάστε περισσότερα

A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes

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 περισσότερα

Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide

Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH 2 CF 3 or ICH 2 CHF 2 Leading to β-cf 3 /CHF 2 -Substituted Ketones Niannian Yi, Hao Zhang, Chonghui Xu, Wei

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General

Διαβάστε περισσότερα

Direct Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines

Direct Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines 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 περισσότερα

Supporting Information

Supporting 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 περισσότερα

Supporting Information

Supporting Information Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and

Διαβάστε περισσότερα

gem-dichloroalkenes for the Construction of 3-Arylchromones

gem-dichloroalkenes for the Construction of 3-Arylchromones Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Pd(OAc)2/S=PPh3 Accelerated Activation of gem-dichloroalkenes for the Construction of 3-Arylchromones

Διαβάστε περισσότερα

Supporting Information

Supporting 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 περισσότερα

Divergent synthesis of various iminocyclitols from D-ribose

Divergent synthesis of various iminocyclitols from D-ribose Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,

Διαβάστε περισσότερα

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan

Διαβάστε περισσότερα

Supporting Information for

Supporting Information for Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a

Διαβάστε περισσότερα

Copper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds. in Aromatic Amides

Copper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds. in Aromatic Amides Supporting Information for Copper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds in Aromatic Amides Feifan Wang, Qiyan Hu, Chao Shu, Zhiyang Lin, Dewen Min, Tianchao Shi and Wu Zhang* Key Laboratory

Διαβάστε περισσότερα

Supplementary 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%. 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 περισσότερα

Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes

Enantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α,

Διαβάστε περισσότερα

Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction

Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 SUPPRTIG IFRMATI Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst-

Διαβάστε περισσότερα

Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran

Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran 1 Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran Munawar Hussain, a Rasheed Ahmad Khera, a Nguyen Thai Hung, a Peter Langer* a,b a Institut für Chemie, Universität Rostock,

Διαβάστε περισσότερα

Copper-Catalyzed Oxidative Coupling of Acids with Alkanes Involving Dehydrogenation: Facile Access to Allylic Esters and Alkylalkenes

Copper-Catalyzed Oxidative Coupling of Acids with Alkanes Involving Dehydrogenation: Facile Access to Allylic Esters and Alkylalkenes Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary information Copper-Catalyzed xidative Coupling of Acids with Alkanes Involving Dehydrogenation:

Διαβάστε περισσότερα

The Free Internet Journal for Organic Chemistry

The Free Internet Journal for Organic Chemistry The Free Internet Journal for Organic Chemistry Paper Archive for Organic Chemistry Arkivoc 2018, part iii, S1-S6 Synthesis of dihydropyranones and dihydropyrano[2,3- d][1,3]dioxine-diones by cyclization

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Ceric Ammonium Nitrate (CAN) catalyzed efficient one-pot three component aza-diels-alder reactions for a facile synthesis of tetrahydropyranoquinoline derivatives Ravinder Goud Puligoundla

Διαβάστε περισσότερα

Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation

Iodine-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 περισσότερα

The N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information.

The N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information. Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2018 The,-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H Carbonylation using

Διαβάστε περισσότερα

Supporting information

Supporting information Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information Copper-catalysed intramolecular O-arylation: a simple

Διαβάστε περισσότερα

Highly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces

Highly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces Highly enantioselective cascade synthesis of spiropyrazolones Alex Zea a, Andrea-Nekane R. Alba a, Andrea Mazzanti b, Albert Moyano a and Ramon Rios a,c * Supporting Information NMR spectra and HPLC traces

Διαβάστε περισσότερα

Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information

Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information 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 περισσότερα

Supporting Information

Supporting Information Supporting Information Selective Synthesis of xygen-containing Heterocycles via Tandem Reactions of 1,2-Allenic Ketones with Ethyl 4-Chloroacetoacetate Qiang Wang, a, b Zhouqing Xu b and Xuesen Fan a *

Διαβάστε περισσότερα

Supporting Information for

Supporting 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 περισσότερα

Vilsmeier Haack reagent-promoted formyloxylation of α-chloro-narylacetamides

Vilsmeier Haack reagent-promoted formyloxylation of α-chloro-narylacetamides Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Vilsmeier aack reagent-promoted formyloxylation of α-chloro-arylacetamides by formamide Jiann-Jyh

Διαβάστε περισσότερα

Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes

Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory

Διαβάστε περισσότερα

First DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of

First DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch

Διαβάστε περισσότερα

and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol

and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu

Διαβάστε περισσότερα

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006

Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006 Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 1 A Facile Way to Synthesize 2H-Chromenes: Reconsideration of the Reaction Mechanism between Salicylic Aldehyde and

Διαβάστε περισσότερα

multicomponent synthesis of 5-amino-4-

multicomponent synthesis of 5-amino-4- Supporting Informartion for Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4- (arylselanyl)-1h-pyrazoles Camila S. Pires 1, Daniela H. de Oliveira 1, Maria R. B. Pontel 1, Jean

Διαβάστε περισσότερα

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Supporting Information Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo* Graduate

Διαβάστε περισσότερα

Supporting Information. Experimental section

Supporting Information. Experimental section Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Proton nuclear magnetic resonance ( 1

Διαβάστε περισσότερα

Facile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang*

Facile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang* 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 περισσότερα

Supporting Information. Experimental section

Supporting Information. Experimental section Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Anhydrous solvents were transferred by

Διαβάστε περισσότερα

Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions

Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions This journal is The Royal Society of Chemistry 213 Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions Wenjing Cui, a Bao Zhaorigetu,* a Meilin Jia, a and Wulan

Διαβάστε περισσότερα

Supporting Information

Supporting 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 περισσότερα

Aminofluorination of Fluorinated Alkenes

Aminofluorination of Fluorinated Alkenes Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Synthesis of ɑ CF 3 and ɑ CF 2 H Amines via Aminofluorination of Fluorinated Alkenes Ling Yang,

Διαβάστε περισσότερα

Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles

Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry SUPPRTIG IFRMATI Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Anahit Pews-Davtyan and Matthias Beller* Leibniz-Institut

Διαβάστε περισσότερα

Supplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;

Supplementary 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 περισσότερα

Supporting Information

Supporting 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 περισσότερα

Supporting Information

Supporting Information Electronic upplementary Material (EI) for Green Chemistry. This journal is The Royal ociety of Chemistry 204 upporting Information ynthesis of sulfonamides via I 2 -mediated reaction of sodium sulfinates

Διαβάστε περισσότερα

Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.

Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section

Διαβάστε περισσότερα

Supplementary Information for

Supplementary 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 περισσότερα

Supporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic

Supporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic 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 περισσότερα

Supporting Information for

Supporting Information for Supporting Information for Palladium-Catalyzed C-H Bond Functionalization of C6-Arylpurines Hai-Ming Guo,* Wei-Hao Rao, Hong-Ying iu, Li-Li Jiang, Ge ng, Jia-Jia Jin, Xi-ing Yang, and Gui-Rong Qu* College

Διαβάστε περισσότερα

Electronic Supplementary Information

Electronic Supplementary Information Electronic Supplementary Information NbCl 3 -catalyzed [2+2+2] intermolecular cycloaddition of alkynes and alkenes to 1,3-cyclohexadiene derivatives Yasushi Obora,* Keisuke Takeshita and Yasutaka Ishii*

Διαβάστε περισσότερα

Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate

Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate upporting Information Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate Jing-Yu Wu, Zhi-Bin Luo, Li-Xin Dai and Xue-Long Hou* a tate Key Laboratory of Organometallic

Διαβάστε περισσότερα

A straightforward metal-free synthesis of 2-substituted thiazolines in air

A straightforward metal-free synthesis of 2-substituted thiazolines in air 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

Διαβάστε περισσότερα

Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination

Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine

Διαβάστε περισσότερα

Supporting Information

Supporting 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 περισσότερα

Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis

Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe

Διαβάστε περισσότερα

Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde. hydrazones leading to N,N -diacylhydrazines and 1,3,4-oxadiazoles

Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde. hydrazones leading to N,N -diacylhydrazines and 1,3,4-oxadiazoles Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde hydrazones leading

Διαβάστε περισσότερα

Supporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds

Supporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds Supporting Information for Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds Zhongxue Fang, a Yongquan Ning, a Pengbing Mi, a Peiqiu Liao, a Xihe Bi* a,b a Department of Chemistry,

Διαβάστε περισσότερα

Supporting Information. Table of Contents. II. Experimental procedures. II. Copies of 1H and 13C NMR spectra for all compounds

Supporting Information. Table of Contents. II. Experimental procedures. II. Copies of 1H and 13C NMR spectra for all compounds Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2017 Laboratoire de Méthodologie et ynthèse de Produit aturels. Université du Québec

Διαβάστε περισσότερα

Supporting Information

Supporting 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 περισσότερα

Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol

Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol Supporting Information for: Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol Yu-Fang Zhang, Diao Chen, Wen-Wen

Διαβάστε περισσότερα

Room Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled

Room Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Supporting Information for: Room Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Stereoselectivity Reversal

Διαβάστε περισσότερα

Supplementary information

Supplementary information Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary information Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles

Διαβάστε περισσότερα

Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols. Support Information

Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols. 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 περισσότερα

Supporting Information

Supporting 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 περισσότερα

Synthesis of unsymmetrical imidazolium salts by direct quaternization of N-substituted imidazoles using arylboronic acids

Synthesis of unsymmetrical imidazolium salts by direct quaternization of N-substituted imidazoles using arylboronic acids Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of unsymmetrical imidazolium salts by direct quaternization

Διαβάστε περισσότερα

9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts

9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer

Διαβάστε περισσότερα

Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu*

Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu* Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 204 Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates (ynones, ynamide): Construction of -Pyrones and 3(2H)-Furanones Starting from Identical Materials Feng Wang,

Διαβάστε περισσότερα

Chiral Brønsted Acid Catalyzed Enantioselective Intermolecular Allylic Aminations. Minyang Zhuang and Haifeng Du*

Chiral 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 περισσότερα

SUPPLEMENTARY MATERIAL

SUPPLEMENTARY 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 περισσότερα

Supporting Information for Synthesis of Fused N-Heterocycles via Tandem C-H Activation

Supporting Information for Synthesis of Fused N-Heterocycles via Tandem C-H Activation This journal is The Royal Society of Chemistry 212 Supporting Information for Synthesis of Fused -Heterocycles via Tandem C-H Activation Ge Meng, Hong-Ying iu, Gui-Rong Qu, John S. Fossey, Jian-Ping Li,*

Διαβάστε περισσότερα

Supplementary Figure 1. (X-ray structures of 6p and 7f) O N. Br 6p

Supplementary Figure 1. (X-ray structures of 6p and 7f) O N. Br 6p Supplementary Figure 1 (X-ray structures of 6p and 7f) Me Br 6p 6p Supplementary Figures 2-68 (MR Spectra) Supplementary Figure 2. 1 H MR of the 6a Supplementary Figure 3. 13 C MR of the 6a Supplementary

Διαβάστε περισσότερα

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2018 Palladium-catalyzed direct approach to α-cf 3 aryl ketones from arylboronic acids Bo

Διαβάστε περισσότερα

Supplementary Material

Supplementary Material Supplementary Material Control experiments S2 Characterization data for the products S2-S7 References S8 MR spectra for the products S9-S28 S1 Control experiments 2a (99.5 mg, 0.5 mmol), I 2 (50.8 mg,

Διαβάστε περισσότερα

D-Glucosamine-derived copper catalyst for Ullmann-type C- N coupling reaction: theoretical and experimental study

D-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 περισσότερα

Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement

Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of novel 1,2,3-triazolyl derivatives of

Διαβάστε περισσότερα

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 15 Supporting Information For Visible-light-induced photocatalytic oxytrifluoromethylation of -allylamides

Διαβάστε περισσότερα

Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes

Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes Supporting Information for Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes Yibiao Li* 1, Liang Cheng 1, Xiaohang Liu

Διαβάστε περισσότερα

Selective mono reduction of bisphosphine

Selective mono reduction of bisphosphine Griffith Research Online https://research-repository.griffith.edu.au Selective mono reduction of bisphosphine oxides under mild conditions Author etersson, Maria, Loughlin, Wendy, Jenkins, Ian ublished

Διαβάστε περισσότερα

ESI for. A simple and efficient protocol for the palladium-catalyzed. ligand-free Suzuki reaction at room temperature in aqueous DMF.

ESI for. A simple and efficient protocol for the palladium-catalyzed. ligand-free Suzuki reaction at room temperature in aqueous DMF. 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 περισσότερα

Phosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions

Phosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions Supplementary Information for Phosphorus xychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions u Chen,* a,b Xunfu Xu, a Liu Liu, a Guo Tang,* a

Διαβάστε περισσότερα

Electronic Supplementary Information (ESI)

Electronic Supplementary Information (ESI) Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Electronic Supplementary Information (ESI) For Iron-Catalysed xidative Amidation of Alcohols with Amines Silvia Gaspa, a Andrea

Διαβάστε περισσότερα

Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with. β-nitroalkenes. Contents. 1. General Information S2

Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with. β-nitroalkenes. Contents. 1. General Information S2 Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with β-nitroalkenes Jing Zheng, Dahai Wang, and Sunliang Cui* College of Pharmaceutical Sciences, Zhejiang University,

Διαβάστε περισσότερα

Supplementary Information for. Singlet excited state of BODIPY promoted aerobic crossdehydrogenative-coupling

Supplementary Information for. Singlet excited state of BODIPY promoted aerobic crossdehydrogenative-coupling Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary Information for Singlet excited state of BODIPY promoted aerobic crossdehydrogenative-coupling

Διαβάστε περισσότερα

Synthesis and evaluation of novel aza-caged Garcinia xanthones

Synthesis 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 περισσότερα

Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors

Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors Andrea Trabocchi a, icolino Pala b, Ilga Krimmelbein c, Gloria Menchi a, Antonio Guarna a, Mario Sechi b, Tobias Dreker c, Andrea Scozzafava

Διαβάστε περισσότερα

Supporting Information

Supporting Information Supporting Information Rhodium-catalyzed Intramolecular Dehydrogenative Aryl Aryl Coupling Using Air as Terminal Oxidant Hannah Baars, 1,2 Yuto Unoh, 1 Takeshi Okada, 1 Koji Hirano, 1 Tetsuya Satoh,* 1,3

Διαβάστε περισσότερα

Supplement: Intramolecular N to N acyl migration in conformationally mobile 1 -acyl-1- systems promoted by debenzylation conditions (HCOONH 4

Supplement: Intramolecular N to N acyl migration in conformationally mobile 1 -acyl-1- systems promoted by debenzylation conditions (HCOONH 4 Cent. Eur. J. Chem. 9(5) 2011 S164-S175 DI: 10.2478/s11532-011-0082-y Central European Journal of Chemistry Supplement: Intramolecular to acyl migration in conformationally mobile 1 -acyl-1- benzyl-3,4

Διαβάστε περισσότερα

Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process

Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process 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 περισσότερα

Supporting information

Supporting information Electronic upplementary Material (EI) for New Journal of Chemistry. This journal is The Royal ociety of Chemistry and the Centre National de la Recherche cientifique 7 upporting information Lipase catalyzed,-addition

Διαβάστε περισσότερα

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br)

Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br) Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using

Διαβάστε περισσότερα

Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL

Zuxiao 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 περισσότερα

Supporting Information

Supporting Information Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2017 Supporting Information 1. General experimental methods (S2). 2. Table 1: Initial studies (S2-S4).

Διαβάστε περισσότερα

Supporting Information for. Palladium-catalyzed Addition Reaction of Aroyl/Heteroaroyl Acid Anhydrides to Norbornenes

Supporting Information for. Palladium-catalyzed Addition Reaction of Aroyl/Heteroaroyl Acid Anhydrides to Norbornenes Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information for Palladium-catalyzed Addition Reaction of Aroyl/Heteroaroyl Acid Anhydrides

Διαβάστε περισσότερα

Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl

Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl 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 περισσότερα

Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes

Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes 1 Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes Gonzalo Blay, Isabel Fernández, Alícia Marco-Aleixandre, and José R. Pedro Departament de Química Orgànica, Facultat de Química,

Διαβάστε περισσότερα

Supporting Information

Supporting Information ynthesis of ubstituted Benzothiazoles via Copper-Catalyzed Condensation of 2-Aminobenzenethiols with itriles Yadong un,, Huanfeng Jiang,*, Wanqing Wu, Wei Zeng, Xia Wu chool of Chemistry and Chemical Engineering,

Διαβάστε περισσότερα