Single-step thioetherification by indium-catalyzed reductive coupling of carboxylic acids with thiols

Organic Letters

Volumn 14, Issue 17, 2012, Pages 4366-4369

  Sakai, Norio ^a   Miyazaki, Takahiro ^a   Sakamoto, Tomohiro ^a   Yatsuda, Takuma ^a   Moriya, Toshimitsu ^a   Ikeda, Reiko ^a   Konakahara, Takeo ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84866051086     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302109v     Document Type: Article

References (72)

1. Larock, R. C. Comprehensive Organic Transformations, 2 nd ed.; Wiley-VCH; New York, 1999.
2. Baird, C. P.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 1998, 1973
3. Hua, G.; Woollins, J. D. Tetrahedron Lett. 2007, 48, 3677
4. Bahrami, K.; Khodaei, M. M.; Khedri, M. Chem. Lett. 2007, 36, 1324
5. Kikuchi, S.; Konishi, H.; Hashimoto, Y. Tetrahedron 2005, 61, 3587
6. Miller, S. J.; Collier, T. R.; Wu, W. Tetrahedron Lett. 2000, 41, 3781
7. Shimizu, M.; Shibuya, K.; Hayakawa, R. Synlett 2000, 1437
8. Wakisaka, M.; Hatanaka, M.; Nitta, H.; Hatamura, M.; Ishimaru, T. Synthesis 1980, 67
9. Gardner, J. N.; Kaiser, S.; Krubiner, A.; Lucas, H. Can. J. Chem. 1973, 51, 1419
10. Han, X.; Wu, J. Org. Lett. 2010, 12, 5780
11. Han, X.; Zhang, Y.; Wu, J. J. Am. Chem. Soc. 2010, 132, 4104
12. Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753
13. Cozzi, P. G.; Zoli, L. Angew. Chem., Int. Ed. 2008, 47, 4162
14. Koval, I. Russ. J. Org. Chem. 2007, 43, 319 and references cited therein
15. Guindon, Y.; Frenette, R.; Fortin, R.; Rokach, J. J. Org. Chem. 1983, 48, 1357
16. Xu, H.-J.; Zhao, Y.-Q.; Feng, T.; Feng, Y.-S. J. Org. Chem. 2012, 77, 2878
17. Rout, L.; Saha, P.; Jammi, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2008, 640
18. Sperotto, E.; van Klink, G. P. M.; de Vries, J. G.; van Koten, G. J. Org. Chem. 2008, 73, 5625
19. Verma, A. K.; Singh, J.; Chaudhary, R. Tetrahedron Lett. 2007, 48, 7199
20. Rout, L.; Sen, T. K.; Punniyamurthy, T. Angew. Chem., Int. Ed. 2007, 46, 5583
21. Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863
22. Zhu, D.; Xu, L.; Wu, F.; Wan, B. Tetrahedron Lett. 2006, 47, 5781
23. Chen, Y. J.; Chen, H. H. Org. Lett. 2006, 8, 5609
24. Bates, C. G.; Saejueng, P.; Doherty, M. Q.; Venkataraman, D. Org. Lett. 2004, 6, 5005
25. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517
26. Lee, P. H.; Park, Y.; Park, S.; Lee, E.; Kim, S. J. Org. Chem. 2011, 76, 760
27. Fernandez-Rodriguez, M. A.; Hartwig, J. F. J. Org. Chem. 2009, 74, 1663
28. Mispelaere-Canivet, C.; Spindler, J.-F.; Perrio, S.; Beslin, P. Tetrahedron 2005, 61, 5253
29. Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397
30. Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587
31. Miller, K. J.; Abu-Omar, M. M. Eur. J. Org. Chem. 2003, 1294
32. Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1985, 58, 3657
33. Jammi, S.; Barua, P.; Rout, L.; Saha, P.; Punniyamurthy, T. Tetrahedron Lett. 2008, 49, 1484
34. Yatsumonji, Y.; Okada, O.; Tsubouchi, A.; Takeda, T. Tetrahedron 2006, 62, 9981
35. Zhang, Y.; Ngeow, K. C.; Ying, J. Y. Org. Lett. 2007, 9, 3495
36. Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2009, 74, 3189
37. Wu, J.-R.; Lin, C.-H.; Lee, C.-F. Chem. Commun. 2009, 4450
38. Reddy, V. P.; Kumar, A. V.; Swapna, K.; Rao, K. R. Org. Lett. 2009, 11, 1697
39. Wong, Y.-C.; Jayanth, T. T.; Cheng, C.-H. Org. Lett. 2006, 8, 5613
40. Bulman Page, P. C.; Klair, S. S.; Brown, M. P.; Smith, C. S.; Maginn, S. J.; Mulley, S. Tetrahedron 1992, 48, 5933
41. Kikugawa, Y. Chem. Lett. 1981, 10, 1157
42. Gellert, B. A.; Kahlcke, N.; Feurer, M.; Roth, S. Chem. - Eur. J. 2011, 17, 12203
43. Wang, Q.; Li, X.-y.; Prakash, G. K. S.; Olah, G. A.; Loker, D. P.; Loker, K. B. ARKIVOC 2001, 116
44. Olah, G. A.; Wang, Q.; Trivedi, N. J.; Surya Prakash, G. K. Synthesis 1992, 465
45. Sassaman, M. B.; Surya Prakash, G. K.; Olah, G. A.; Donald, P.; Loker, K. B. Tetrahedron 1988, 44, 3771
46. Sakai, N.; Usui, Y.; Ikeda, R.; Konakahara, T. Adv. Synth. Catal. 2011, 353, 3397
47. Sakai, N.; Nagasawa, K.; Ikeda, R.; Nakaike, Y.; Konakahara, T. Tetrahedron Lett. 2011, 52, 3133
48. Sakai, N.; Kawana, K.; Ikeda, R.; Nakaike, Y.; Konakahara, T. Eur. J. Org. Chem. 2011, 3178
49. Sakai, N.; Fujii, K.; Nabeshima, S.; Ikeda, R.; Konakahara, T. Chem. Commun. 2010, 46, 3173
50. Sakai, N.; Moritaka, K.; Konakahara, T. Eur. J. Org. Chem. 2009, 4123
51. Sakai, N.; Moriya, T.; Fujii, K.; Konakahara, T. Synthesis 2008, 3533
52. Sakai, N.; Fujii, K.; Konakahara, T. Tetrahedron Lett. 2008, 49, 6873
53. Sakai, N.; Moriya, T.; Konakahara, T. J. Org. Chem. 2007, 72, 5920
54. Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2005, 46, 6407
55. Pehlivan, L.; Metay, E.; Delbrayelle, D.; Mignani, G.; Lemaire, M. Tetrahedron 2012, 68, 3151
56. Tsuchimoto, T.; Wagatsuma, T.; Aoki, K.; Shimotori, J. Org. Lett. 2009, 11, 2129
57. Babu, S. A.; Yasuda, M.; Baba, A. Org. Lett. 2007, 9, 405
58. Miura, K.; Tomita, M.; Yamada, Y.; Hosomi, A. J. Org. Chem. 2007, 72, 787
59. Benati, L.; Bencivenni, G.; Leardini, R.; Nanni, D.; Minozzi, M.; Spagnolo, P.; Scialpi, R.; Zanardi, G. Org. Lett. 2006, 8, 2499
60. Yasuda, M.; Saito, T.; Ueba, M.; Baba, A. Angew. Chem., Int. Ed. 2004, 43, 1414
61. Shibata, I.; Kato, H.; Ishida, T.; Yasuda, M.; Baba, A. Angew. Chem., Int. Ed. 2004, 43, 711
62. Hayashi, N.; Shibata, I.; Baba, A. Org. Lett. 2004, 6, 4981
63. Miura, K.; Yamada, Y.; Tomita, M.; Hosomi, A. Synlett 2004, 1985
64. Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han, J. S.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1991, 64, 2524
65. Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han, J. S.; Kobayashi, S. Chem. Lett. 1990, 19, 2239
66. Kim, S.; Ho Park, J.; Lee, S. Tetrahedron Lett. 1989, 30, 6697
67. Reductive conversion from carboxylic acids to S,S -acetals was reported; see: Kim, S.; Kim, S. S. Tetrahedron Lett. 1987, 28, 1913
68. 3, see: Bublitz, D. E. J. Org. Chem. 1967, 32, 1630
69. Kim, S.; Kim, S. S.; Lim, S. T.; Shim, S. C. J. Org. Chem. 1987, 52, 2114
70. A reductive C-S bond cleavage of an S,S -acetal by a metal hydride complex was reported; see: Ikeshita, K.-i.; Kihara, N.; Sonoda, M.; Ogawa, A. Tetrahedron Lett. 2007, 48, 3025
71. Nishimoto, Y.; Okita, A.; Yasuda, M.; Baba, A. Org. Lett. 2012, 14, 1846
72. An O,S -acetal, which was prepared in situ by an aldehyde and a thiosilane, was readily reduced to produce the corresponding thioether; see: Glass, R. S. Synth. Commun. 1976, 6, 47