Aromatic Allylsulfenylation with in Situ Generated Allylic Thiols under the Heck Conditions

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 2, 1997, Pages 445-456

  Harayama, Hiroto ^a   Nagahama, Takayuki ^a   Kozera, Toyohiro ^a   Kimura, Masanari ^a   Fugami, Keigo ^a   Tanaka, Shuji ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000389787     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.445     Document Type: Article

References (30)

1. J. B. Melpolder and R. F. Heck, J. Org. Chem., 41, 265 (1976); Y. Tamaru, Y. Yamada, and Z. Yoshida, Tetrahedron Lett., 1977, 3365.
2. J. B. Melpolder and R. F. Heck, J. Org. Chem., 41, 265 (1976); Y. Tamaru, Y. Yamada, and Z. Yoshida, Tetrahedron Lett., 1977, 3365.
3. K. Ono, K. Fugami, S. Tanaka, and Y. Tamaru, Tetrahedron Lett., 35, 4133 (1994).
4. H. Harayama, T. Kozera, M. Kimura, S. Tanaka, and Y. Tamaru, Chem. Lett., 1996, 543.
5. Rearrangement of imidazolylthiocarbamates: a) R. C. Schnur and M. L. Corman, J. Org. Chem., 59, 2581 (1994); b) K. C. Nicolaou and R. D. Groneberg, J. Am. Chem. Soc., 112, 4085 (1990). Rearrangement of N,N-dimethylthiocarbamates: c) R. E. Hackler and T. W. Balko, J. Org. Chem., 38, 2106 (1973).
6. Rearrangement of imidazolylthiocarbamates: a) R. C. Schnur and M. L. Corman, J. Org. Chem., 59, 2581 (1994); b) K. C. Nicolaou and R. D. Groneberg, J. Am. Chem. Soc., 112, 4085 (1990). Rearrangement of N,N-dimethylthiocarbamates: c) R. E. Hackler and T. W. Balko, J. Org. Chem., 38, 2106 (1973).
7. Rearrangement of imidazolylthiocarbamates: a) R. C. Schnur and M. L. Corman, J. Org. Chem., 59, 2581 (1994); b) K. C. Nicolaou and R. D. Groneberg, J. Am. Chem. Soc., 112, 4085 (1990). Rearrangement of N,N-dimethylthiocarbamates: c) R. E. Hackler and T. W. Balko, J. Org. Chem., 38, 2106 (1973).
8. A. G. Myers and K. R. Condroski, J. Am. Chem. Soc., 117, 3057 (1995); S. Harusawa and T. Kurihara, Yuki Gosei Kagaku Kyokai Shi, 53, 712 (1995).
9. A. G. Myers and K. R. Condroski, J. Am. Chem. Soc., 117, 3057 (1995); S. Harusawa and T. Kurihara, Yuki Gosei Kagaku Kyokai Shi, 53, 712 (1995).
10. B. M. Trost and H. Hiemstra, J. Am. Chem. Soc., 104, 886 (1982); K. Harano and T. Taguchi. Chem. Pharm. Bull., 20, 2348 (1972).
11. B. M. Trost and H. Hiemstra, J. Am. Chem. Soc., 104, 886 (1982); K. Harano and T. Taguchi. Chem. Pharm. Bull., 20, 2348 (1972).
12. P. R. Auburn, J. Whelan, and B. Bosnich, Organometallics, 5, 1533 (1986).
13. Y. Tamaru, K. Nagao, T. Bando, and Z. Yoshida, J. Org. Chem., 55, 1823 (1990).
14. R. F. Heck, "Palladium Reagents in Organic Synthesis," Academic, London (1985), Chap. 3.
15. 4 catalyzed conversion of allylic acetates into allylic amines with inversion of configuration: B. M. Trost and E. Keinan, J. Am. Chem. Soc., 100, 7779 (1978). Allylic sulfonamide with retention of configuration: S. E. Bystrmöm, R. Aslanian, and J.-E. Bäckvall, Tetrahedron Lett., 26, 1749 (1985).
16. 4 catalyzed conversion of allylic acetates into allylic amines with inversion of configuration: B. M. Trost and E. Keinan, J. Am. Chem. Soc., 100, 7779 (1978). Allylic sulfonamide with retention of configuration: S. E. Bystrmöm, R. Aslanian, and J.-E. Bäckvall, Tetrahedron Lett., 26, 1749 (1985).
17. Aromatic amination: F. Paul, J. Patt, and J. F. Hartwig, J. Am. Chem. Soc., 116, 5969 (1994); A. S. Guram and S. L. Buchwald, J. Am. Chem. Soc., 116, 7901 (1994); D. Baranano and J. F. Hartwig, J. Am. Chem. Soc., 117, 2937 (1995); M. Meller, Angew. Chem., Int. Ed. Engl., 34, 1316 (1995).
18. Aromatic amination: F. Paul, J. Patt, and J. F. Hartwig, J. Am. Chem. Soc., 116, 5969 (1994); A. S. Guram and S. L. Buchwald, J. Am. Chem. Soc., 116, 7901 (1994); D. Baranano and J. F. Hartwig, J. Am. Chem. Soc., 117, 2937 (1995); M. Meller, Angew. Chem., Int. Ed. Engl., 34, 1316 (1995).
19. Aromatic amination: F. Paul, J. Patt, and J. F. Hartwig, J. Am. Chem. Soc., 116, 5969 (1994); A. S. Guram and S. L. Buchwald, J. Am. Chem. Soc., 116, 7901 (1994); D. Baranano and J. F. Hartwig, J. Am. Chem. Soc., 117, 2937 (1995); M. Meller, Angew. Chem., Int. Ed. Engl., 34, 1316 (1995).
20. Aromatic amination: F. Paul, J. Patt, and J. F. Hartwig, J. Am. Chem. Soc., 116, 5969 (1994); A. S. Guram and S. L. Buchwald, J. Am. Chem. Soc., 116, 7901 (1994); D. Baranano and J. F. Hartwig, J. Am. Chem. Soc., 117, 2937 (1995); M. Meller, Angew. Chem., Int. Ed. Engl., 34, 1316 (1995).
21. a) T. Migita, T. Shimizu, Y. Asami, J. Shiobara, Y. Kato, and M. Kosugi, Bull. Chem. Soc. Jpn., 53, 1385 (1980);
22. b) M. Kosugi, T. Ogata, M. Terada, H. Sano, and T. Migita, Bull. Chem. Soc. Jpn., 58, 3657 (1985);
23. c) M. J. Dickens, J. P. Gilday, T. J. Mowlem, and D. A. Widdowson, Tetrahedron, 47, 8621 (1991).
24. S.-I. Murahashi, M. Yamamura, K. Yanagisawa, N. Mita, and K. Kondo, J. Org. Chem., 44, 2408 (1979); A. Carpita, R. Rossi, and B. Scamuzzi, Tetrahedron Lett., 30, 2699 (1989); A. G. Martinez, J. O. Barcina, A. de F. Cerezo, and L. R. Subramanian, Synlett, 1994, 561.
25. S.-I. Murahashi, M. Yamamura, K. Yanagisawa, N. Mita, and K. Kondo, J. Org. Chem., 44, 2408 (1979); A. Carpita, R. Rossi, and B. Scamuzzi, Tetrahedron Lett., 30, 2699 (1989); A. G. Martinez, J. O. Barcina, A. de F. Cerezo, and L. R. Subramanian, Synlett, 1994, 561.
26. S.-I. Murahashi, M. Yamamura, K. Yanagisawa, N. Mita, and K. Kondo, J. Org. Chem., 44, 2408 (1979); A. Carpita, R. Rossi, and B. Scamuzzi, Tetrahedron Lett., 30, 2699 (1989); A. G. Martinez, J. O. Barcina, A. de F. Cerezo, and L. R. Subramanian, Synlett, 1994, 561.
27. K. Kondo and I. Ojima, J. Chem. Soc., Chem. Commun., 1972, 62.
28. K.-C. Kong and C.-H. Chen, J. Am. Chem. Soc., 113, 6313 (1991); M. Sakamoto, I. Shimizu, and A. Yamamoto, Chem. Lett., 1995, 1101; B. E. Segelstein, T. W. Bulter, and B. L. Chenard, J. Org. Chem., 60, 12 (1995).
29. K.-C. Kong and C.-H. Chen, J. Am. Chem. Soc., 113, 6313 (1991); M. Sakamoto, I. Shimizu, and A. Yamamoto, Chem. Lett., 1995, 1101; B. E. Segelstein, T. W. Bulter, and B. L. Chenard, J. Org. Chem., 60, 12 (1995).
30. K.-C. Kong and C.-H. Chen, J. Am. Chem. Soc., 113, 6313 (1991); M. Sakamoto, I. Shimizu, and A. Yamamoto, Chem. Lett., 1995, 1101; B. E. Segelstein, T. W. Bulter, and B. L. Chenard, J. Org. Chem., 60, 12 (1995).