Synthesis of Stereodefined Enynes by the Nickel-Catalyzed Coupling Reaction of Alkynyltins, Alkynes, and Enones

Journal of the American Chemical Society

Volumn 116, Issue 13, 1994, Pages 5975-5976

  Ikeda, Shin Ichi ^a   Sato, Yoshiro ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343289843     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00092a061     Document Type: Article

References (9)

1. Kosugi, M.; Migita, T. J. Synth. Org. Chem. Jpn. 1980, 38, 1142. Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Mitchell, T. N. Synthesis 1992, 803.
2. Recent papers: Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434. Ye, J.; Bhatt, R. K.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 1.
3. 2 catalyzed a conjugate addition of alkenyltins to enals, see: Grisso, B. A.; Johnson, J. R.; Mackenzie, P. B. J. Am. Chem. Soc. 1992, 114, 5160.
4. 4 in situ, see: Negishi, E.; Baba, S. J. Chem. Soc., Chem. Commun. 1976, 596.
5. Johnson, J. R.; Tully, P. S.; Mackenzie, P. B.; Sabat, M. J. Am. Chem. Soc. 1991, 113, 6172.
6. Chiusoli, G. P.; Cassar, L. Angew. Chem., Int. Ed. Engl. 1967, 6, 124. Chiusoli, G. P. Pure Appl. Chem. 1971, 6, 169. Chiusoli, G. P. Acc. Chem. Res. 1973, 6, All. Casser, L.; Chiusoli, G. P.; Guerrieri, F. Synthesis 1973, 509.
7. Both Ni(I)/Ni(III) and Ni(0)/Ni(II) active catalyst systems have been proposed for related processes. For examples of Ni(I)/Ni(III) systems, see: Kochi, J. K. Pure Appl. Chem. 1980, 52, 571. Dayrit, F. M.; Schwartz, J. J. Am. Chem. Soc. 1981, 103, 4466. Hegedus, L. S.; Thompson, D. H. P. J. Am. Chem. Soc. 1985, 107, 5663. For an example of Ni(0)/Ni(II) systems, see ref 3.
8. Ni-catalyzed coupling reaction of organic halides with tetramethyltin and carbon monoxide was reported, see: Tanaka, M. Synthesis 1981, 47.
9. For recent papers on the synthesis of conjugated enynes, see: Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. Tetrahedron Lett. 1992, 33, 5363. Luo, F.-T.; Fwu, S.-L.; Huang, W.-S. Tetrahedron Lett. 1992, 33, 6839. Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A. Tetrahedron Lett. 1993, 34, 2139. Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991.