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Nickel-Catalyzed Intermolecular [2 + 2] Cycloaddition of Conjugated Enynes with Alkenes

Akira Nishimura, Masato Ohashi and Sensuke Ogoshi*

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: ogoshichem.eng.osaka-u.ac.jp

A. Nishimura, M. Ohashi, S. Ogoshi, J. Am. Chem. Soc., 2012, 134, 15692-15695.

DOI: 10.1021/ja3074775



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Abstract

A nickel-catalyzed intermolecular [2 + 2] cycloaddition of conjugated enynes with electron-deficient alkenes as well as electronically neutral norbornene leads to cyclobutenes. The use of conjugated enynes circumvented possible side rections, such as oligomerizations and cyclotrimerizations. η3-Butadienyl coordination is the key for the selective formation of cyclobutenes.

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Key Words

cyclobutenes


ID: J48-Y2012-3070