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Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins

Ryosuke Matsubara, Alicia C. Gutierrez and Timothy F. Jamison*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email:

R. Matsubara, A. C. Gutierrez, T. F. Jamison, J. Am. Chem. Soc., 2011, 133, 19020-19023.

DOI: 10.1021/ja209235d


Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes with benzyl chlorides provides functionalized allylbenzene derivatives. In contrast to analogous palladium-catalyzed processes, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins with very high selectivity.

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Simplifying Nickel(0) Catalysis: An Air-Stable Nickel Precatalyst for the Internally Selective Benzylation of Terminal Alkenes

E. A. Standley, T. F. Jamison, J. Am. Chem. Soc., 2013, 135, 1585-1592.

Key Words

olefination, benzylation

ID: J48-Y2011-3320