Metal-catalyzed addition of phosphine and methanesulfonic acid to alkyne [9]

Journal of the American Chemical Society

Volumn 122, Issue 10, 2000, Pages 2387-2388

  Arisawa, Mieko ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; MESYLIC ACID; METAL; PHOSPHINE;

CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034653665     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9937728     Document Type: Letter

References (25)

1. Reviews: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. Kelly, S. E. Alkene Synthesis. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Chapter 3.1, Vol. 1, p 729.
2. Reviews: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863. Kelly, S. E. Alkene Synthesis. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Chapter 3.1, Vol. 1, p 729.
3. An uncatalyzed reaction of phosphine and unactivated alkyne giving alkenylphosphine is reported: Barsegyan, S. K.; Gasparyan, G. Ts.; Ovakimyan, M. Zh.; Indzhikyan, M. G. J. Gen. Chem. USSK 1990, 60, 859. Metalcatalyzed addition reaction of phosphorous compounds possessing P-H bonds: Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. 1998, 37, 94. Addition of phosphine to activated alkynes: Nozaki, K.; Sato, N.; Ikeda, K. Takaya, H. J. Org. Chem. 1996, 61, 4516 and references therein.
4. An uncatalyzed reaction of phosphine and unactivated alkyne giving alkenylphosphine is reported: Barsegyan, S. K.; Gasparyan, G. Ts.; Ovakimyan, M. Zh.; Indzhikyan, M. G. J. Gen. Chem. USSK 1990, 60, 859. Metalcatalyzed addition reaction of phosphorous compounds possessing P-H bonds: Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. 1998, 37, 94. Addition of phosphine to activated alkynes: Nozaki, K.; Sato, N.; Ikeda, K. Takaya, H. J. Org. Chem. 1996, 61, 4516 and references therein.
5. An uncatalyzed reaction of phosphine and unactivated alkyne giving alkenylphosphine is reported: Barsegyan, S. K.; Gasparyan, G. Ts.; Ovakimyan, M. Zh.; Indzhikyan, M. G. J. Gen. Chem. USSK 1990, 60, 859. Metalcatalyzed addition reaction of phosphorous compounds possessing P-H bonds: Han, L.-B.; Hua, R.; Tanaka, M. Angew. Chem., Int. Ed. 1998, 37, 94. Addition of phosphine to activated alkynes: Nozaki, K.; Sato, N.; Ikeda, K. Takaya, H. J. Org. Chem. 1996, 61, 4516 and references therein.
6. For recent examples, see: Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424. Okada, Y.; Minami, T.; Yahiro, S.; Akinaga, K. J. Org. Chem. 1989, 54, 974. Lee, P. H.; Kim, J. S.; Kim, Y. C.; Kim, S. Tetrahedron Lett. 1993, 34, 7583. Byrley, I. Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985. Bitterer, F.; Kucken, S.; Stelzer, O. Chem. Ber. 1995, 128, 275. Okuma, K.; Ikari, K.; Ono, M.; Sato, Y.; Kuge, S.; Ohta, H.; Machiguchi, T. Bull. Chem. Soc. Jpn. 1995, 68, 2313. Shen, Y.; Yao, J. J. Org. Chem. 1996, 61, 8659. Miedaner, A.; Noll, B. C.; DuBois, D. L. Organometallics 1997, 16, 5779. Hanamoto, T.; Kiguchi, Y.; Shindo, K.; Matsuoka, M.; Kondo, M. J. Chem. Soc. Chem. Commun. 1999, 151.
7. For recent examples, see: Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424. Okada, Y.; Minami, T.; Yahiro, S.; Akinaga, K. J. Org. Chem. 1989, 54, 974. Lee, P. H.; Kim, J. S.; Kim, Y. C.; Kim, S. Tetrahedron Lett. 1993, 34, 7583. Byrley, I. Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985. Bitterer, F.; Kucken, S.; Stelzer, O. Chem. Ber. 1995, 128, 275. Okuma, K.; Ikari, K.; Ono, M.; Sato, Y.; Kuge, S.; Ohta, H.; Machiguchi, T. Bull. Chem. Soc. Jpn. 1995, 68, 2313. Shen, Y.; Yao, J. J. Org. Chem. 1996, 61, 8659. Miedaner, A.; Noll, B. C.; DuBois, D. L. Organometallics 1997, 16, 5779. Hanamoto, T.; Kiguchi, Y.; Shindo, K.; Matsuoka, M.; Kondo, M. J. Chem. Soc. Chem. Commun. 1999, 151.
8. For recent examples, see: Posner, G. H.; Lu, S.-B. J. Am. Chem. Soc. 1985, 107, 1424. Okada, Y.; Minami, T.; Yahiro, S.; Akinaga, K. J. Org. Chem. 1989, 54, 974. Lee, P. H.; Kim, J. S.; Kim, Y. C.; Kim, S. Tetrahedron Lett. 1993, 34, 7583. Byrley, I. Hewson, A. T. Tetrahedron Lett. 1994, 35, 7099. Clerici, F.; Gelmi, M. L.; Pocar, D.; Rondena, R. Tetrahedron 1995, 51, 9985. Bitterer, F.; Kucken, S.; Stelzer, O. Chem. Ber. 1995, 128, 275. Okuma, K.; Ikari, K.; Ono, M.; Sato, Y.; Kuge, S.; Ohta, H.; Machiguchi, T. Bull. Chem. Soc. Jpn. 1995, 68, 2313. Shen, Y.; Yao, J. J. Org. Chem. 1996, 61, 8659. Miedaner, A.; Noll, B. C.; DuBois, D. L. Organometallics 1997, 16, 5779. Hanamoto, T.; Kiguchi, Y.; Shindo, K.; Matsuoka, M.; Kondo, M. J. Chem. Soc. Chem. Commun. 1999, 151.
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