메뉴 건너뛰기




Volumn 121, Issue 22, 1999, Pages 5108-5114

Highly regio- and stereocontrolled synthesis of vinyl sulfides via transition-metal-catalyzed hydrothiolation of alkynes with thiols

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; PALLADIUM COMPLEX; RHODIUM DERIVATIVE; THIOL DERIVATIVE; VINYL DERIVATIVE;

EID: 0033538289     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983949i     Document Type: Article
Times cited : (276)

References (45)
  • 2
    • 1542529331 scopus 로고    scopus 로고
    • Transition Metal Sulfur Chemistry: Biological and Industrial Significance
    • American Chemical Society: Washington, DC
    • (b) Stiefel, E. I.; Matsumoto, K., Eds. Transition Metal Sulfur Chemistry: Biological and Industrial Significance; ACS Symp. Ser. 653; American Chemical Society: Washington, DC, 1996.
    • (1996) ACS Symp. Ser. , vol.653
    • Stiefel, E.I.1    Matsumoto, K.2
  • 23
    • 0012362874 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1982) Chem. Soc. Rev. , vol.11 , pp. 493
    • Ager, D.J.1
  • 24
    • 0000947750 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1984) Bull. Chem. Soc. Jpn. , vol.57 , pp. 1863
    • Takeda, T.1    Furukawa, H.2    Fujimori, M.3    Suzuki, K.4    Fujiwara, T.5
  • 25
    • 84989423687 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1977) Synthesis , pp. 357
    • Gröbel, B.-T.1    Seebach, D.2
  • 26
    • 0020789617 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5075
    • Trost, B.M.1    Lavoie, A.C.2
  • 27
    • 33845378722 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1985) J. Org. Chem. , vol.50 , pp. 1621
    • Magnus, P.1    Quagliato, D.2
  • 28
    • 1542794576 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1988) Tetrahedron , vol.44 , pp. 6755
    • De Lucchi, O.1    Pasquato, L.2
  • 29
    • 0001202342 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1962) Org. React. , vol.12 , pp. 356
    • Pettit, G.R.1    Van Tamelen, E.E.2
  • 30
    • 37049137149 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1973) J. Chem. Soc., Perkin Trans. 1 , pp. 654
    • Boar, R.B.1    Hawkins, D.W.2    McGhie, J.F.3    Barton, D.H.R.4
  • 31
    • 0001339943 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3463
    • Trost, B.M.1    Ornstein, P.L.2
  • 32
    • 37049110784 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1982) J. Chem. Soc., Chem. Commun. , pp. 840
    • Wenkert, E.1    Ferreira, T.W.2
  • 33
    • 37049088962 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1990) J. Chem. Soc., Chem. Commun. , pp. 1284
    • Hojo, M.1    Tanimoto, S.2
  • 34
    • 0001607430 scopus 로고
    • For the synthetic utility of vinyl sulfides, see, for example: (a) Ager, D. J. Chem. Soc. Rev. 1982, 11, 493. (b) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. (c) Gröbel, B.-T.; Seebach, D. Synthesis 1977, 357. (d) Trost, B. M.; Lavoie, A. C. J. Am. Chem. Soc. 1983, 105, 5075. (e) Magnus, P.; Quagliato, D. J. Org. Chem. 1985, 50, 1621. (f) De Lucchi, O.; Pasquato, L. Tetrahedron 1988,44, 6755. (g) Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356. (h) Boar, R. B.; Hawkins, D. W.; McGhie, J. F.; Barton, D. H. R. J. Chem. Soc., Perkin Trans. 1 1973, 654. (i) Trost, B. M.; Ornstein, P. L. Tetrahedron Lett. 1981, 22, 3463. (j) Wenkert, E.; Ferreira, T. W. J. Chem. Soc., Chem. Commun. 1982, 840. (k) Hojo, M.; Tanimoto, S. J. Chem. Soc., Chem. Commun. 1990, 1284. (l) Hojo, M.; Harada, H.; Yoshizawa, J.; Hosomi, A. J. Org. Chem. 1993, 58, 6541.
    • (1993) J. Org. Chem. , vol.58 , pp. 6541
    • Hojo, M.1    Harada, H.2    Yoshizawa, J.3    Hosomi, A.4
  • 41
    • 0032537669 scopus 로고    scopus 로고
    • and refs 2l,m,o
    • Also, see: (b) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Sonoda, N. Tetrahedron Lett. 1992, 33, 5525. (c) Ogawa, A.; Kudo, A.; Hirao, T. Tetrahedron Lett. 1998, 39, 5213, and refs 2l,m,o.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5213
    • Ogawa, A.1    Kudo, A.2    Hirao, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.