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

Eric A. Standley and Timothy F. Jamison*

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

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

DOI: 10.1021/ja3116718


The air-stable nickel(II) complex trans-(PCy2Ph)2Ni(o-tolyl)Cl enables an internally selective Mizoroki-Heck-type coupling of substituted benzyl chlorides with terminal alkenes at room temperature. This operationally simple and highly regioselective reaction provides rapid, convergent access to substituted allylbenzene derivatives in high yield and can be carried out on the benchtop with no purification or degassing of solvents or reagents.

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

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

Key Words

benzylation, alkenylation

ID: J48-Y2013-0260