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: tfjmit.edu
R. Matsubara, A. C. Gutierrez, T. F. Jamison, J. Am. Chem. Soc., 2011, 133, 19020-19023.
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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E. A. Standley, T. F. Jamison, J. Am. Chem. Soc., 2013, 135, 1585-1592.