Copper-catalyzed regioselective allylic substitution reactions with indium organometallics.

Rodríguez, D.; Pérez Sestelo, J.; Sarandeses, L. A.


J. Org. Chem. 2003, 68, 2518–2520 (DOI: 10.1021/jo0265939).

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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 SN2’ product.