Palladium-catalyzed azathiolation of carbon monoxide

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7305-7308

  Kuniyasu, Hitoshi ^a   Hiraike, Hiroshi ^a   Morita, Masaki ^a   Tanaka, Aoi ^a   Sugoh, Kunihiko ^a   Kurosawa, Hideo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0033214813     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9823137     Document Type: Article

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38. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
39. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
40. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
41. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
42. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
43. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
44. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
45. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
46. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
47. The definitive evidences of insertion of CO into the M-S bond have been very rare, (a) Antebi, S.; Alper, H. Organometallics 1986, 5, 596. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609. (c) Shim, S. C.; Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935. (d) Takahashi, H.; Ohe, K.; Uemura, S.; Sugita, N. J. Organomet. Chem. 1987, 334, C43. (e) Wang, M. D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. (f) Kim, Y. J.; Osakada, K.; Sugita, K.; Yamamoto, T.; Yamamoto, A. Organometallics 1988, 7, 2182. (g) Liu, H.; Tan, A. L.; Mok, K. F.; Hor, T. S. A. J. Chem. Soc., Dalton Trans. 1996, 4023. (h) Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. (i) Matsunaga, P. T.; Hillhouse, G. L. Angew. Chem., Int. Engl. 1994, 33, 1748. (j) Khumtaveeporn, K.; Alper, H. J. Org. Chem. 1994, 59, 1414. See also ref 1g and 6b.
48. We have recently reported that the insertions of isocyanide into Pd-S bond of 4 was reversible and its equilibrium leaned to the deinsertion direction; see: Kuniyasu, H.; Sugoh, K; Moon, S.; Kurosawa, H. J. Am. Chem. Soc. 1997, 119, 4669.
49. 4 was very sluggish (2% after 12 h at rt).
50. A bond metathesis between S-B and Pd-C bonds has been recently reported; see: Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1998, 17, 1383.