Organic Letters 2010-04-02

Cyclopropylmethylation of benzylic and allylic chlorides with cyclopropylmethylstannane catalyzed by gallium or indium halide.

Kensuke Kiyokawa, Makoto Yasuda, Akio Baba

Index: Org. Lett. 12(7) , 1520-3, (2010)

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Abstract

Benzylic and allylic chlorides easily coupled with cyclopropylmethylstannane in the presence of GaCl(3) or InBr(3) catalyst, in which an intermediate of an active butenylgallium or -indium species was confirmed by NMR spectroscopy and X-ray analysis. An ionic reaction process is plausible for this coupling.