Synthesis of a wide range of thioethers by indium triiodide catalyzed direct coupling between alkyl acetates and thiosilanes

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1846-1849

  Nishimoto, Yoshihiro ^a   Okita, Aya ^a   Yasuda, Makoto ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; INDIUM; IODINE DERIVATIVE; SILANE DERIVATIVE; SULFIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ACETATES; CATALYSIS; INDIUM; IODINE COMPOUNDS; MOLECULAR STRUCTURE; SILANES; SULFIDES;

EID: 84859564094     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300450j     Document Type: Article

References (57)

1. Peach, M. E. In The Chemistry of the Thiol Group; Patai, S., Ed.; John Wiley & Sons: London, 1979; pp 721-756.
2. Damani, L. A. In Sulfur-Containing Drugs and Related Organic Compounds: Chemistry, Biochemistry, and Toxicology; Ellis Horwood Ltd.: Chichester, UK, 1989; Vol. 1, Part B: Metabolism of Sulfur Functional Groups.
3. Oae, S., Ed. Organic Sulfur Chemistry: Structure and Mechanism; CRC Press: Boca Raton, 1991.
4. Cremlyn, R. J. In An Introduction to Organosulfur Chemistry; Wiley & Sons: New York, 1996.
5. McReynolds, M. D.; Doughtery, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239
6. Parham, W. E.; Wynberg, H. Org. Synth. 1963, 4, 295
7. Boscato, J. F.; Catala, J. M.; Franta, E.; Brossas, J. Tetrahedron Lett. 1980, 21, 1519
8. Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. A. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073
9. Malmstrom, J.; Gupta, V.; Engman, L. J. Org. Chem. 1998, 63, 3318
10. Blanchard, P.; Jousselme, B.; Frere, P.; Roncali, J. J. Org. Chem. 2002, 67, 3961
11. Ranu, B. C.; Jana, R. Adv. Synth. Catal. 2005, 1811
12. Guindon, Y. R.; Frenette, R.; Fortin, J.; Rokach, J. J. Org. Chem. 1983, 48, 1357
13. Ouertani, M.; Collin, J.; Kagan, H. B. Tetrahedron 1985, 41, 3689
14. Kawada, A.; Yasuda, K.; Abe, H.; Harayama, T. Chem. Pharm. Bull. 2002, 50, 380
15. Ohmori, K.; Ushimaru, N.; Suzuki, K. Tetrahedron Lett. 2002, 43, 7753
16. Zhan, Z. P.; Yu, J. L.; Liu, H. J.; Cui, Y. Y.; Yang, R. F.; Yang, W. Z.; Li, J. P. J. Org. Chem. 2006, 71, 8298
17. Han, X.; Wu, J. Org. Lett. 2010, 12, 5780
18. Inomata, K.; Yamamoto, T.; Kotake, H. Chem. Lett. 1981, 1357
19. Trost, B. M.; Scanlan, T. S. Tetrahedron Lett. 1986, 27, 4141
20. Goux, C.; Lhoste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099
21. Kondo, T.; Morisaki, Y.; Uenoyama, S.; Wada, K.; Mitsudo, T. J. Am. Chem. Soc. 1999, 121, 8657
22. Nakagawa, H.; Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2004, 69, 3474
23. Yatsumonji, Y.; Ishida, Y.; Tsubouchi, A.; Takeda, T. Org. Lett. 2007, 9, 4603
24. Tanaka, S.; Pradhan, P. K.; Maegawa, Y.; Kitamura, M. Chem. Commun. 2010, 46, 3996
25. Ruthenium-catalyzed propargylic substitution reaction: Inada, Y.; Nishibayashi, Y.; Hidai, M.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 15172
26. Carroll, F. I.; White, J. D.; Wall, M. J. Org. Chem. 1963, 28, 1236
27. Lehr, H.; Karlan, S.; Goldberg, M. W. J. Med. Chem. 1963, 6, 136
28. Carroll, F. I.; White, J. D.; Wall, M. E. J. Org. Chem. 1963, 28, 1240
29. Ono, N.; Kamimura, A.; Kaji, A. Tetrahedron Lett. 1986, 27, 1595
30. Selva, M.; Trotta, F.; Tundo, P. J. Chem. Soc., Perkin Trans. 2 1992, 519
31. Otera, J.; Nakazawa, K.; Sekoguchi, K.; Orita, A. Tetrahedron 1997, 53, 13633
32. Paulitz, C.; Steglich, W. J. Org. Chem. 1997, 62, 8474
33. Xu, F.; Shi, W.; Wang, J. J. Org. Chem. 2005, 70, 4191
34. Kuroda, K.; Maruyama, Y.; Hayashi, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2009, 82, 381
35. Lee, H. S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2009, 50, 6480
36. Saha, A.; Ranu, B. C. Tetrahedron Lett. 2010, 51, 1902
37. Nakagawa, I.; Hata, T. Tetrahedron Lett. 1975, 17, 1409
38. Mukaiyama, T.; Ikegai, K. Chem. Lett. 2004, 1522
39. Yasuda, M.; Saito, T.; Ueba, M.; Baba, A. Angew. Chem., Int. Ed. 2004, 43, 1414
40. Saito, T.; Yasuda, M.; Baba, A. Synlett 2005, 1737
41. Saito, T.; Nishimoto, Y.; Yasuda, M.; Baba, A. J. Org. Chem. 2006, 71, 8516
42. Huang, J.-M.; Wong, C.-M.; Xub, F.-X.; Loh, T.-P. Tetrahedron Lett. 2007, 48, 3375
43. Baba, A.; Yasuda, M.; Nishimoto, Y.; Saito, T.; Onishi, Y. Pure Appl. Chem. 2008, 80, 845
44. Nishimoto, Y.; Kajioka, M.; Saito, T.; Yasuda, M.; Baba, A. Chem. Commun. 2008, 6396
45. Nishimoto, Y.; Onishi, Y.; Yasuda, M.; Baba, A. Angew. Chem., Int. Ed. 2009, 48, 9131
46. Nishimoto, Y.; Saito, T.; Yasuda, M.; Baba, A. Tetrahedron 2009, 65, 5462
47. Nishimoto, Y.; Moritoh, R.; Yasuda, M.; Baba, A. Angew. Chem., Int. Ed. 2009, 48, 4577
48. Nishimoto, Y.; Inamoto, Y.; Saito, T.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2010, 3382
49. Nishimoto, Y.; Ueda, H.; Inamoto, Y.; Yasuda, M.; Baba, A. Org. Lett. 2010, 12, 3390
50. Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A. Org. Lett. 2011, 13, 2762
51. Nishimoto, Y.; Okita, A.; Yasuda, M.; Baba, A. Angew. Chem., Int. Ed. 2011, 50, 8623
52. Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A. Chem. Lett. 2011, 40, 1223
53. Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705
54. Schwier, T.; Rubin, M.; Gevorgyan, V. Org. Lett. 2004, 6, 1999
55. Rubenbauer, P.; Bach, T. Tetrahedron Lett. 2008, 49, 1305
56. Rubenbauer, P.; Herdtweck, E.; Strassner, T.; Bach, T. Angew. Chem., Int. Ed. 2008, 47, 10106
57. Node, M.; Nishide, K.; Ochiai, M.; Fuji, K.; Fujita, E. J. Org. Chem. 1981, 46, 5163