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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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Publication details

The article was received on 21 Dec 2017, accepted on 21 Feb 2018 and first published on 22 Feb 2018


Article type: Edge Article
DOI: 10.1039/C7SC05420C
Citation: Chem. Sci., 2018,9, 3215-3220
  • Open access: Creative Commons BY-NC license
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    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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