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Issue 12, 2018
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Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies

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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.

Graphical abstract: Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies

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Article information


Submitted
21 Dec 2017
Accepted
21 Feb 2018
First published
22 Feb 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 3215-3220
Article type
Edge Article

Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies

J. P. Phelan, R. J. Wiles, S. B. Lang, C. B. Kelly and G. A. Molander, Chem. Sci., 2018, 9, 3215
DOI: 10.1039/C7SC05420C

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