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

Kensuke Kiyokawa; Makoto Yasuda; Akio Baba

doi:10.1021/ol100240b

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

Org Lett. 2010 Apr 2;12(7):1520-3. doi: 10.1021/ol100240b.

Authors

Kensuke Kiyokawa¹, Makoto Yasuda, Akio Baba

Affiliation

¹ Department of Applied Chemistry, Center for Atomic and Molecular Technologies, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 20218636
DOI: 10.1021/ol100240b

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Cyclopropanes / chemical synthesis*
Cyclopropanes / chemistry
Gallium / chemistry*
Hydrocarbons, Chlorinated / chemistry*
Indium / chemistry*
Models, Molecular
Molecular Structure
Organotin Compounds / chemistry*
Stereoisomerism

Substances

Cyclopropanes
Hydrocarbons, Chlorinated
Organotin Compounds
cyclopropylmethylstannane
Indium
indium trichloride
gallium chloride
Gallium