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

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 Peter...

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Autores principales: Phelan, James P., Wiles, Rebecca J., Lang, Simon B., Kelly, Christopher B., Molander, Gary A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5916225/
https://www.ncbi.nlm.nih.gov/pubmed/29732105
http://dx.doi.org/10.1039/c7sc05420c
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author Phelan, James P.
Wiles, Rebecca J.
Lang, Simon B.
Kelly, Christopher B.
Molander, Gary A.
author_facet Phelan, James P.
Wiles, Rebecca J.
Lang, Simon B.
Kelly, Christopher B.
Molander, Gary A.
author_sort Phelan, James P.
collection PubMed
description 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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spelling pubmed-59162252018-05-04 Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies Phelan, James P. Wiles, Rebecca J. Lang, Simon B. Kelly, Christopher B. Molander, Gary A. Chem Sci Chemistry 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. Royal Society of Chemistry 2018-02-22 /pmc/articles/PMC5916225/ /pubmed/29732105 http://dx.doi.org/10.1039/c7sc05420c Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Phelan, James P.
Wiles, Rebecca J.
Lang, Simon B.
Kelly, Christopher B.
Molander, Gary A.
Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies
title Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies
title_full Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies
title_fullStr Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies
title_full_unstemmed Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies
title_short Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies
title_sort rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5916225/
https://www.ncbi.nlm.nih.gov/pubmed/29732105
http://dx.doi.org/10.1039/c7sc05420c
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