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. 2014 May 26;20(22):6613-7.
doi: 10.1002/chem.201402218. Epub 2014 Apr 29.

Synthesis of cyclobutenes and allenes by cobalt-catalyzed cross-dimerization of simple alkenes with 1,3-enynes

Akira Nishimura  1 , Eri Tamai, Masato Ohashi, Sensuke Ogoshi
Affiliations

Synthesis of cyclobutenes and allenes by cobalt-catalyzed cross-dimerization of simple alkenes with 1,3-enynes

Akira Nishimura et al. Chemistry. .

Abstract

Cobalt-catalyzed cross-dimerization of simple alkenes with 1,3-enynes is reported. A [2+2] cycloaddition reaction occurred, with alkenes bearing no allylic hydrogen, by reductive elimination of a η(3)-butadienyl cobaltacycle. On the other hand, aliphatic alkenes underwent 1,4-hydroallylation by means of exo-cyclic β-H elimination. These reactions can provide cyclobutenes and allenes that were previously difficult to access, from simple substrates in a highly chemo- and regioselective manner.

Keywords: 1,3-enyenes; alkenes; allenes; cobalt; cyclobutene.

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