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

Grégory Landelle; Pier Alexandre Champagne; Xavier Barbeau; Jean-François Paquin

doi:10.1021/ol8027412

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

Org Lett. 2009 Feb 5;11(3):681-4. doi: 10.1021/ol8027412.

Authors

Grégory Landelle¹, Pier Alexandre Champagne, Xavier Barbeau, Jean-François Paquin

Affiliation

¹ Canada Research Chair in Organic and Medicinal Chemistry, Département de chimie, 1045 avenue de la Médecine, Université Laval, Québec, QC, Canada G1V 0A6.

PMID: 19143558
DOI: 10.1021/ol8027412

Abstract

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.

Publication types

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

MeSH terms

Alkenes / chemical synthesis*
Alkenes / chemistry*
Catalysis
Hydrocarbons, Brominated / chemical synthesis
Hydrocarbons, Brominated / chemistry
Hydrocarbons, Fluorinated / chemical synthesis*
Hydrocarbons, Fluorinated / chemistry*
Molecular Structure
Palladium / chemistry
Silanes / chemistry*
Stereoisomerism

Substances

Alkenes
Hydrocarbons, Brominated
Hydrocarbons, Fluorinated
Silanes
Palladium