LiCl-mediated preparation of functionalized benzylic indium(III) halides and highly chemoselective palladium-catalyzed cross-coupling in a protic cosolvent

Yi-Hung Chen; Mai Sun; Paul Knochel

doi:10.1002/anie.200805588

LiCl-mediated preparation of functionalized benzylic indium(III) halides and highly chemoselective palladium-catalyzed cross-coupling in a protic cosolvent

Angew Chem Int Ed Engl. 2009;48(12):2236-9. doi: 10.1002/anie.200805588.

Authors

Yi-Hung Chen¹, Mai Sun, Paul Knochel

Affiliation

¹ Department Chemie & Biochemie, Ludwig Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München, Germany.

PMID: 19199325
DOI: 10.1002/anie.200805588

Abstract

Sensitive functional groups such as COR, CHO, or CH(2)OH can be present in benzylic indium reagents prepared by the direct insertion of indium in the presence of LiCl. These reagents undergo palladium-catalyzed cross-coupling reactions in the presence of a protic cosolvent after activation with iPrMgCl x LiCl (see scheme). Remarkable chemoselectivities are achieved by using various electrophiles containing NH or OH groups.