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Ni(II)-Catalyzed Conia-Ene Reaction of 1,3-Dicarbonyl Compounds with Alkynes

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Qiang Gao, Bao-Fu Zheng, Jin-Heng Li, and Dan Yang*

Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China

Org. Lett., 2005, 7 (11), pp 2185–2188

DOI: 10.1021/ol050532q

Publication Date (Web): May 6, 2005

Section:

Alicyclic Compounds

Abstract

We have discovered a Ni(II)-catalyzed Conia-ene reaction of 1,3-dicarbonyl compounds with alkynes. In the presence of Ni(acac)₂ and Yb(OTf)₃, various acetylenic 1,3-dicarbonyl compounds underwent Conia-ene reaction to give mono- and bicyclic olefinic cyclopentanes. A mechanism involving the enol−yne−Ni complex formation is proposed and supported by deuterium-labeling experiments.

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