Rapid synthesis of aryl sulfides through metal-free C-S coupling of thioalcohols with diaryliodonium salts

Tetrahedron Letters

Volumn 55, Issue 42, 2014, Pages 5739-5741

  Wang, Dawei ^a   Yu, Xin ^a   Zhao, Keyan ^a   Li, Liang ^a   Ding, Yuqiang ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

Chemoselectivity; CS coupling; Diaryliodonium; Metal free; Rapid

Indexed keywords

ALCOHOL DERIVATIVE; DIARYLIODONIUM SALT; ORGANOIODINE DERIVATIVE; SULFIDE; THIOL; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; REACTION TIME; ROOM TEMPERATURE; SCREENING TEST; SYNTHESIS;

EID: 84908410427     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.08.088     Document Type: Article

References (85)

1. For some reviews, see: T.W. Lyons, and M.S. Sanford Chem. Rev. 110 2010 1147 1169
2. I.A. Mkhalid, J.H. Barnard, T.B. Marder, J.M. Murphy, and J.F. Hartwig Chem. Rev. 110 2010 890 931
3. J.F. Hartwig Acc. Chem. Res. 41 2008 1534 1544
4. J.C. Lewis, R.G. Bergman, and J.A. Ellman Acc. Chem. Res. 41 2008 1013 1025
5. S.V. Ley, and A.W. Thomas Angew. Chem., Int. Ed. 42 2003 5400 5449
6. K. Kunz, U. Scholz, and D. Ganzer Synlett 2003 2428 2439
7. T. Kondo, and T. Mitsudo Chem. Rev. 100 2000 3205 3220
8. For some reviews and examples for C-S(N, O) cross coupling, see: F. Han Chem. Soc. Rev. 42 2013 5270 5289
9. C.J. Seechurn, M.O. Kitching, T.J. Colacot, and V. Snieckus Angew. Chem., Int. Ed. 51 2012 5062 5085
10. E. Negishi, Z. Huang, G. Wang, S. Mohan, C. Wang, and H. Hattori Acc. Chem. Res. 41 2008 1474 1485
11. I.P. Beletskaya, and A.V. Cheprakov Coord. Chem. Rev. 248 2004 2337 2364
12. S. Jammi, S. Sakthivel, L. Rout, T. Mukherjee, S. Mandal, R. Mitra, P. Saha, and T. Punniyamurthy J. Org. Chem. 74 2009 1971 1976
13. P.S. Fier, and J.F. Hartwig Angew. Chem., Int. Ed. 52 2013 2092 2095
14. C. Chen, Z. Weng, and J.F. Hartwig Organometallics 31 2012 8031 8037
15. P.S. Fier, and J.F. Hartwig J. Am. Chem. Soc. 134 2012 10795 10798
16. P.S. Fier, and J.F. Hartwig J. Am. Chem. Soc. 134 2012 5524 5527
17. M.A. Fernández-Rodríguez, Q. Shen, and J.F. Hartwig J. Am. Chem. Soc. 128 2006 2180 2181
18. M.A. Düfert, K.L. Billingsley, and S.L. Buchwald J. Am. Chem. Soc. 135 2013 12877 12885
19. J.R. DeBergh, N. Niljianskul, and S.L. Buchwald J. Am. Chem. Soc. 135 2013 10638 10641
20. T.D. Senecal, W. Shu, and S.L. Buchwald Angew. Chem., Int. Ed. 52 2013 10035 10039
21. G. Teverovskiy, D.S. Surry, and S.L. Buchwald Angew. Chem., Int. Ed. 50 2011 7312 7314
22. F.Y. Kwong, and S.L. Buchwald Org. Lett. 4 2002 3517 3520
23. H. Yuan, M. Wang, Y. Liu, and Q. Liu Adv. Synth. Catal. 351 2009 112 116
24. C. Piao, Y. Zhao, X. Han, and Q. Liu J. Org. Chem. 73 2008 2264 2269
25. F. Liang, J. Zhang, J. Tan, and Q. Liu Adv. Synth. Catal. 348 2006 1986 1990
26. I.P. Beletskaya, and V.P. Ananikov Chem. Rev. 111 2011 1596 1636
27. C.S. Bryan, J.A. Braunger, and L. Mark Angew. Chem., Int. Ed. 48 2009 7064 7068
28. Z.-Y. Duan, S. Ranjit, P.-F. Zhang, and X.-G. Liu Chem. Eur. J. 15 2011 3666 3669
29. M. Cong, Y.-T. Fan, J.H. Raimundo, Y. Xia, Y. Liu, G. Quelever, F-Q. Qu, and L. Peng Chem. Eur. J. 19 2013 17267 17272
30. Y. Hirai, and Y. Uozumi Chem. Lett. 40 2011 934 935
31. H. Lin, X.-C. Dong, Y.-X. Li, Q.-L. Shen, and L. Lu Chem. Eur. J. 46 2007 5583 5586
32. Z.-J. Qiao, J.-P. Wei, and X.-F. Jiang Org. Lett. 16 2014 1212 1215
33. F.-L. Zeng, and H. Alper Org. Lett. 13 2011 2868 2871
34. M. Kuhn, F.C. Falk, and J. Paradies Org. Lett. 13 2011 4100 4103
35. L. Rout, T.K. Sen, and T. Punniyamurthy Angew. Chem., Int. Ed. 48 2009 7064 7068
36. S.M. Soria-Castro, and A.B. Penenory Beilstein J. Org. Chem. 9 2013 467 475
37. J. Mondal, A. Modak, A. Dutta, and A. Bhaumik Dalton Trans. 40 2011 5228 5235
38. R.-S. Xu, J.-P. Wan, H. Mao, and Y.-J. Pan J. Am. Chem. Soc. 132 2010 15531 15533
39. X. Lv, and W.-L. Bao J. Org. Chem. 72 2007 3863 3867
40. E. Sperotto, G.P.M. van Klink, J.G. de Vries, and K. van Koten J. Org. Chem. 73 2008 5625 5628
41. T. Ramana, P. Saha, M. Das, and T. Punniyamurthy Org. Lett. 12 2010 84 87
42. S. Ranjit, Z.-Y. Duan, P.-F. Zhang, and X.-G. Liu Org. Lett. 12 2010 4134 4136
43. E. Sperotto, G.P.M. van Klink, J.G. de Vries, and G. van Koten Tetrahedron 66 2010 9009 9020
44. S.G. Babu, and R. Karvembu Tetrahedron Lett. 54 2013 1677 1680
45. Y.-G. Zhang, K.C. Ngeow, and J.-Y. Ying Org. Lett. 9 2007 3495 3498
46. X.-B. Xu, J. Liu, J.-J. Zhang, Y.-W. Wang, and Y. Peng Org. Lett. 15 2013 550 553
47. J. Zhang, C.M. Medley, J.A. Krause, and H.-R. Guan Organometallics 29 2010 6393 6401
48. S. Tamba, K. Fuji, K. Nakamura, and A. Mori Organometallics 33 2014 12 15
49. P. Guan, C.-S. Cao, Y. Liu, Y.-F. Li, P. He, Q. Chen, G. Liu, and Y.-H. Shi Tetrahedron Lett. 53 2012 5987 5992
50. R. Das, and D. Chakraborty Tetrahedron Lett. 53 2012 7023 7027
51. V.P. Reddy, A.V. Kumar, K. Swapna, and K.R. Rao Org. Lett. 11 2009 1697 1700
52. E. Sperotto, P.M. van Klink, J.G. de Vries, and G. van Koten J. Org. Chem. 73 2008 5625 5628
53. J. Ranjit, Z.-Y. Duan, P.-F. Zhang, and X.-G. Liu Org. Lett. 12 2010 4134 4136
54. Y.-S. Feng, Y.-Y. Li, L. Tang, W. Wu, and H.-J. Xu Tetrahedron Lett. 51 2010 2489 2492
55. Y.-S. Feng, H.-X. Qi, W.-C. Wang, Y.-F. Liang, and H.-J. Xu Tetrahedron Lett. 53 2012 2914 2917
56. Bandna, N.R. Guha, A.K. Shil, D. Sharma, and P. Das Tetrahedron Lett. 53 2012 5318 5322
57. B.Y. Bhong, A.V. Shelke, and N.N. Karade Tetrahedron Lett. 54 2013 739 743
58. J.-H. Cheng, C. Ramesh, H.-L. Kao, Y.-J. Wang, C.-C. Chan, and C.-F. Lee J. Org. Chem. 77 2012 10369 10374
59. I.M. Yonova, C.A. Osborne, N.S. Morrissette, and E.R. Jarvo J. Org. Chem. 79 2014 1947 1953
60. M. Walter, K. Isensee, T. Kottke, X. Ligneau, J.-C. Camelin, J.-C. Schwartz, and H. Stark Bioorg. Med. Chem. Lett. 20 2010 5883 5886
61. F. Eroglu, D. Kahya, and E. Erdik J. Organomet. Chem. 695 2010 267 270
62. W.S. Ojo, F.Y. Petillon, P. Schollhammer, and J. Talarmin Organometallics 27 2008 4207 4222
63. Z.-Q. Ni, S.-C. Wang, H. Mao, and Y.-J. Pan Tetrahedron Lett. 53 2012 3907 3910
64. V.V. Zhdankin, and P.J. Stang Chem. Rev. 108 2008 5299 5358
65. Z.-C. Xiao, and C.-F. Xia Chin. J. Org. Chem. 33 2013 2119 2130
66. For some reviews and papers, see: B.S.L. Collins, M.G. Suero, and M.J. Gaunt Angew. Chem., Int. Ed. 52 2013 5799 5802
67. J. Peng, C. Chen, Y. Wang, Z.-B. Lou, M. Li, C.-J. Xi, and H. Chen Angew. Chem., Int. Ed. 52 2013 7574 7578
68. J. Guo, S.-X. Dong, Y.-L. Zhang, Y.-L. Kuang, X.-H. Liu, L.-L. Lin, and X.-M. Feng Angew. Chem., Int. Ed. 52 2013 10245 10249
69. J.S. Ho, L.C. Misal Castro, Y. Aihara, M. Tobisu, and N. Chatani Asian J. Org. Chem. 3 2014 48 51
70. X. Su, C. Chen, Y. Wang, J.-J. Chen, Z.-B. Lou, and M. Li Chem. Commun. 2013 6752 6754
71. R.-B. Hu, H. Zhang, X.-Y. Zhang, and S.-D. Yang Chem. Commun. 2014 2193 2195
72. M.G. Suero, E.D. Bayle, B.S.L. Collins, and M.J. Gaunt J. Am. Chem. Soc. 135 2013 5332 5335
73. Q.-L. Xu, H.-Y. Gao, M. Yousufuddin, D.H. Ess, and L. Kurti J. Am. Chem. Soc. 135 2013 14048 14051
74. T.-Y. Lv, Z. Wang, J.-S. You, J.-B. Lan, and G. Gao J. Org. Chem. 78 2013 5723 5730
75. A.M. Wagner, and M.S. Sanford J. Org. Chem. 79 2014 2263 2267
76. N. Umierski, and G. Manolikakes Org. Lett. 15 2013 188 191
77. N. Gigant, L.C. Boissarie, M.C. Belhomme, T. Poisson, X. Pannecoucke, and I. Gillaizeau Org. Lett. 15 2013 278 281
78. F.-L. Guo, J.-W. Han, S. Mao, J. Li, X. Geng, J.-J. Yu, and L.-M. Wang RSC Adv. 3 2013 6267 6270
79. S.C. Cullen, S. Shekhar, and N.K. Nere J. Org. Chem. 78 2013 12194 12201
80. N. Jalalian, E.E. Ishikawa, L.F. Silva Jr., and B. Olofsson Org. Lett. 13 2011 1552 1555
81. T.B. Petersen, R. Khan, and B. Olofsson Org. Lett. 13 2011 3462 3465
82. J.Z. You, and Z.C. Chen Synth. Commun. 22 1992 1441 1444
83. N. Jalalian, T.B. Petersen, and B. Olofsson Chem. Eur. J. 18 2012 14140 14149
84. J. Malmgren, S. Santoro, N. Jalalian, F. Himo, and B. Olofsson Chem. Eur. J. 19 2013 10334 10342
85. H.P. de Magalha¯es, H.P. Lüthi, and A. Togni Org. Lett. 14 2012 3830 3833