Rapid Access to Diverse, Trifluoromethyl-substituted Alkenes Using Complementary Strategies

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2018 May 8

PMID 29732105

Citations 6

Authors

James P Phelan

Rebecca J Wiles

Simon B Lang

Christopher B Kelly

Gary A Molander

Affiliations

Soon will be listed here.

Abstract

Two synergistic approaches to the facile assembly of complex α-trifluoromethyl alkenes are described. Using α-trifluoromethyl-β-silyl alcohols as masked trifluoromethyl alkenes, cross-coupling or related functionalization processes at distal electrophilic sites can be executed without inducing Peterson elimination. Subsequent Lewis acidic activation affords functionalized α-trifluoromethyl alkenes. Likewise, the development of a novel α-trifluoromethylvinyl trifluoroborate reagent complements this approach and allows a one-step cross-coupling of (hetero)aryl halides to access a broad array of complex α-trifluoromethyl alkenes.

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