Copper-catalyzed regioselective allylic substitution reactions with indium organometallics

J Org Chem. 2003 Mar 21;68(6):2518-20. doi: 10.1021/jo0265939.

Abstract

The first nucleophilic allylic substitution reactions of triorganoindium compounds with allylic halides and phosphates are reported. The reactions of trialkyl- and triarylindium reagents with cinnamyl and geranyl halides and phosphates, with the aid of copper catalysis [Cu(OTf)(2)/P(OEt)(3)], are described. In general, the reaction proceeds efficiently to give good yields and regioselectively to afford the S(N)2' product.