Nickel(0)-Catalyzed Hydroacylation of Alkynes with Aldehydes to α,β-Enones

Journal of Organic Chemistry

Volumn 55, Issue 8, 1990, Pages 2554-2558

  Tsuda, Tetsuo ^a   Kiyoi, Takao ^a   Saegusa, Takeo ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751553536     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00295a061     Document Type: Article

References (10)

1. Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 3140.
2. Tauda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. J. Am. Chem. Soc. 1988, 110, 8570.
3. The mechanistic discussion on the formation of α,β-enones may be applicable to that of α,β, γ,δ-dienones.
4. For simplification, the phosphine ligand coordinated toward the nickel atom is omitted in Scheme I.
5. The hydridoacylmetal complex is generally accepted as a key intermediate in the transition metal complex catalyzed hydroacylation of alkenes with aldehydes; see, for example: (a) Vora, K. P.; Locow, C. F.; Miller, R. G. J. Organomet. Chem. 1980, 192, 257.
6. Kondo, T.; Tsuji, Y.; Watanabe, Y. Tetrahedron Lett. 1987, 28, 6229 and the cited references.
7. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2956.
8. Pressurizing the reactions of l-2a and 9a-2c with CO gas (25 kg/cm2) inhibited the formation of the corresponding a,0-enones.
9. The intermediacy of the RCONiH complex may also be possible in the previously reported Ni(0)-catalyzed reaction of diynes and aldehydes. In this reaction mechanism, bicyclic a-pyrans may be formed by electrocyclic ring closure of α,β;γ, δ-dienone intermediates.
10. Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes, and Cumulenes; Elsevier: New York, 1981; p 57.