Stereocontrolled approach to bromofluoroalkenes and their use for the synthesis of tri- and tetrasubstituted fluoroalkenes.

Org Lett

Canada Research Chair in Organic and Medicinal Chemistry, Département de chimie, 1045 avenue de la Médecine, Université Laval, Québec, QC, Canada G1V 0A6.

Published: February 2009

An addition/elimination reaction of organolithium reagents to silylated beta,beta-difluorostyrene derivatives followed by a bromination/desilicobromination reaction provides a simple and effective synthetic approach to a wide range of bromofluoroalkenes (up to >97/3). In addition, the bromofluoroalkenes can be used in Pd-catalyzed transformations giving access to both tri- and tetrasubstituted fluoroalkenes.

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http://dx.doi.org/10.1021/ol8027412DOI Listing

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