Efficient C-S Cross-Coupling of Thiols with Aryl Iodides
calcd for C12H11NOS, 217.0561, found 217.0558.
126.7, 126.3, 124.4, 32.5, 31.4, 27.7, 22.5, 14.1; HRMS
m/z (%): calcd for C11H15NO2S, 225.0823 (M+), found
225.0825.
Pentyl(phenyl)sulfane (10a) Yield 85%, colorless
1
oil; H NMR (300 MHz, CDCl3) δ: 7.13-7.33 (m, 5H,
ArH), 2.91 (t, J=7.3 Hz, 2H, CH2), 1.64-1.68 (m, 2H,
CH2), 1.29-1.40 (m, 4H, 2CH2), 0.89 (t, J=6.6 Hz, 3H,
CH3); 13C NMR (100 MHz, CDCl3) δ: 137.2, 129.0,
128.9, 125.8, 33.7, 31.2, 29.0, 22.5, 14.2; HRMS M+,
calcd for C11H16S, 180.0973, found 180.0972.
(4-Fluoropenyl)(phentyl)sulfane (10h)
Yield
79%, colorless oil; 1H NMR (300 MHz, CDCl3) δ: 7.31
-7.35 (m, 2H, ArH), 6.96-7.01 (m, 2H, ArH), 2.86 (t,
J=15 Hz, 2H, CH2), 1.57-1.61 (m, 2H, CH2), 1.31-
1.39 (m, 4H, 2CH2), 0.89 (t, J=6.9 Hz, 3H, CH3); 13C
NMR (75 MHz, CDCl3) δ: 138.1, 132.4 (J=7.9 Hz),
130.7, 116.3 (J=21.8 Hz), 35.4, 31.3, 29.3, 22.7, 14.3;
HRMS M + , calcd for C11H15FS, 198.0878, found
198.0896.
(4-Methoxypenyl)(phentyl)sulfane (10b)
Yield
82%, colorless oil; 1H NMR (300 MHz, CDCl3) δ: 7.33
(d, J=8.6 Hz, 2H, ArH), 6.83 (d, J=8.6 Hz, 2H, ArH),
3.78 (s, 3H, OCH3), 2.80 (t, J=7.3 Hz, 2H, CH2), 1.53
-1.60 (m, 2H, CH2), 1.26-1.34 (m, 4H, 2CH2), 0.87 (t,
J=6.6 Hz, 3H, CH3); 13C NMR (100 MHz, CDCl3) δ:
158.7, 133.1, 127.1, 114.7, 55.6, 36.0, 31.0, 29.2, 22.5,
14.2; HRMS M+, calcd for C12H18OS, 210.1078, found
210.1078.
(4-Bromopenyl)(phentyl)sulfane (10i) Yield 82%,
1
colorless oil; H NMR (300 MHz, CDCl3) δ: 7.39 (d,
J=8.6 Hz, 2H, ArH), 7.17 (d, J=8.6 Hz, 2H, ArH),
2.89 (t, J=7.5 Hz, 2H, CH2), 1.61-1.66 (m, 2H, CH2),
1.26-1.43 (m, 4H, 2CH2), 0.89 (t, J=7.1 Hz, 3H, CH3);
13C NMR (100 MHz, CDCl3) δ: 136.5 132.0, 130.7,
130.5, 119.5, 33.8, 31.1, 28.7, 22.4, 14.2; HRMS M+,
calcd for C11H15BrS, 258.0078, found 258.0078.
Pentyl(p-tolyl)sulfane (10c) Yield 84%, colorless
1
oil; H NMR (300 MHz, CDCl3) δ: 7.25 (d, J=8.0 Hz,
2H, ArH), 7.10 (d, J=7.9 Hz, 2H, ArH), 2.88 (t, J=7.4
Hz, 2H, CH2), 2.32 (s, 3H, CH3), 1.60-1.66 (m, 2H,
CH2) ,1.27-1.43 (m, 4H, 2CH2), 0.90 (t, J=6.9 Hz, 3H,
CH3); 13C NMR (75 MHz, CDCl3) δ: 136.2, 133.6,
130.2, 130.0, 34.7, 31.4, 29.4, 22.7, 21.5, 14.5; HRMS
M+, calcd for C12H18S, 194.1129, found 194.1130.
Pentyl(m-tolyl)sulfane (10d) Yield 85%, colorless
Acknowledgement
This work was supported by the Team Innovation
Project of Soochow University.
1
References
oil; H NMR (300 MHz, CDCl3) δ: 7.11-7.17 (m, 3H,
ArH), 6.97 (d, J=7.0 Hz, 1H, ArH), 2.91 (t, J=7.4 Hz,
2H, CH2), 2.33 (s, 3H, CH3), 1.60-1.70 (m, 2H, CH2),
1.32-1.44 (m, 4H, 2CH2), 0.90 (t, J=7.1 Hz, 3H, CH3);
13C NMR (75 MHz, CDCl3) δ: 139.0, 137.2, 129.9,
129.1, 126.9, 126.2, 33.9, 31.5, 29.3, 22.7, 21.8, 14.4;
HRMS M + , calcd for C12H18S, 194.1129, found
194.1127.
[1] (a) Procter, D. J. J. Chem. Soc. Perkin Trans. 1 2001, 335; (b) Liu,
G.; Huth, J. R.; Olejniczak, R. T.; Mendoza, F.; Fesik, S. W.; Von
Geldern, T. W. J. Med. Chem. 2001, 44, 1202; (c) Hassan, J.; Sévi-
gnon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102,
1359; (d) Martino, G. D.; Edler, M. C.; Regina, G. L.; Coluccia, A.;
Barbera, M. C.; Barrow, D.; Nicholson, R. I.; Chiosis, G.; Brancale,
A.; Hamel, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2006, 49, 947;
(e) Beletskaya, I. P.; Ananikov, V. P. Eur. J. Org. Chem. 2007, 3431;
(f) Kadlor, S. W.; Kalish, V. J.; Davies, J. F.; Shetty, B. V.; Fritz, J.
E.; Appelt, K.; Burgess, J. A.; Campanale, K. M.; Chirgadze, N. Y.;
Clawson, D. K.; Dressman, B. A.; Hatch, S. D.; Khalil, D. A.; Kosa,
M. B.; Lubbehusen, P. P.; Muesing, M. A.; Patick, A. K.; Reich, S.
H.; Su, K. S.; Tatlock, J. H. J. Med. Chem. 1997, 40, 3979.
[2] (a) Lindley, J. Tetrahedron 1984, 40, 1433; (b) Yamamoto, T.; Se-
kine, Y. Can. J. Chem. 1984, 62, 1544; (c) Hickman, R. J. S.;
Christie, B. J.; Guy, R. W.; White, T. J. Aust. J. Chem. 1985, 38, 899;
(d) Bierbeek, A.V.; Gingras, M. Tetrahedron Lett. 1998, 39, 6283.
[3] (a) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Ko-
sugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385; (b) Kosugi, M.;
Ogata, T.; Terada, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn.
1985, 58, 3657.
[4] (a) Dickens, M. J.; Gilday, J. P.; Mowlem, T. J.; Widdowson, D. A.
Tetrahedron 1991, 47, 8621; (b) Ishiyama, T.; Mori, M.; Suzuki, A.;
Miyaura, N. J. Organomet. Chem. 1996, 525, 225; (c) Zheng, N.;
McWilliams, J. C.; Fleitz, F. J.; Armstrong, J. D.; Volante, R. P. J.
Org. Chem. 1998, 63, 9606; (d) Mann, G.; Baranano, D.; Hartwig, J.
F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205;
(e) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513. (f) Schopfer, U.;
Schlapbach, A. Tetrahedron 2001, 57, 3069; (g) Itoh, T.; Mase, T.
Org. Lett. 2004, 6, 4587; (h) Murata, M.; Buchwald, S. L. Tetrahe-
dron 2004, 60, 7397; (i) Canivet, C. M.; Spindler, J. F.; Perrio, S.;
Beslin, P. Tetrahedron 2005, 61, 5253; (j) Fernandez-Rodriguez, M.
A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180; (k)
Alvaro, E.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 7858; (l)
Pentyl(o-tolyl)sulfane (10e) Yield 92%, colorless
1
oil; H NMR (300 MHz, CDCl3) δ: 7.24-7.26 (m, 1H,
ArH), 7.14-7.17 (m, 2H, ArH), 7.05-7.10 (m, 1H,
ArH), 2.90 (t, J=7.4 Hz, 2H, CH2), 2.37 (s, 3H, CH3),
1.63-1.70 (m, 2H, CH2), 1.30-1.40 (m, 4H, 2CH2),
0.91 (t, J=7.1 Hz, 3H, CH3); 13C NMR (75 MHz,
CDCl3) δ: 139.0, 137.6, 136.8, 130.4, 127.6, 125.6, 33.2,
31.6, 29.1, 22.7, 20.8, 14.4; HRMS M+, calcd for
C12H18S, 194.1129, found 194.1128.
(4-Nitropenyl)(phentyl)sulfane (10f) Yield 92%,
1
yellow oil; H NMR (300 MHz, CDCl3) δ: 8.10 (d, J=
8.8 Hz, 2H, ArH), 7.29 (d, J=8.8 Hz, 2H, ArH), 3.00 (t,
J=7.4 Hz, 2H, CH2), 1.66-1.74 (m, 2H, CH2), 1.31-
1.46 (m, 4H, 2CH2), 0.90 (t, J=7.0 Hz, 3H, CH3); 13C
NMR (100 MHz, CDCl3) δ: 139.0, 145.0, 126.1, 124.1,
32.1, 31.2, 28.3, 22.4, 14.4; HRMS M+, calcd for
C11H15NO2S, 225.0823, found 225.0824.
(2-Nitropenyl)(phentyl)sulfane (10g) Yield 95%,
1
yellow oil; H NMR (300 MHz, CDCl3) δ: 8.18 (d, J=
8.2 Hz, 1H, ArH), 7.51-7.56 (m, 1H, ArH), 7.40 (d, J
=8.1 Hz, 1H, ArH), 7.24 (d, J=8.4 Hz, 1H, ArH), 2.94
(t, J=7.3 Hz, 2H, CH2), 1.68-1.76 (m, 2H, CH2), 1.32
-1.47 (m, 4H, 2CH2), 0.90 (t, J=7.0 Hz, 3H, CH3);
13C NMR (100 MHz, CDCl3) δ: 146.1, 138.5, 133.6,
Chin. J. Chem. 2014, 32, 212—218
© 2014 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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