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Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts

The arylation of alkyl and aromatic terminal alkynes by a dual gold/photoredox catalytic system is described. Using aryldiazonium salts as readily available aryl sources, a range of diversely-functionalized arylalkynes could be synthesized under mild, base-free reaction conditions using visible ligh...

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Detalles Bibliográficos
Autores principales: Tlahuext-Aca, Adrian, Hopkinson, Matthew N., Sahoo, Basudev, Glorius, Frank
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5950757/
https://www.ncbi.nlm.nih.gov/pubmed/29861968
http://dx.doi.org/10.1039/c5sc02583d
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author Tlahuext-Aca, Adrian
Hopkinson, Matthew N.
Sahoo, Basudev
Glorius, Frank
author_facet Tlahuext-Aca, Adrian
Hopkinson, Matthew N.
Sahoo, Basudev
Glorius, Frank
author_sort Tlahuext-Aca, Adrian
collection PubMed
description The arylation of alkyl and aromatic terminal alkynes by a dual gold/photoredox catalytic system is described. Using aryldiazonium salts as readily available aryl sources, a range of diversely-functionalized arylalkynes could be synthesized under mild, base-free reaction conditions using visible light from simple household sources or even sunlight. This process, which exhibits a broad scope and functional group tolerance, expands the range of transformations amenable to dual gold/photoredox catalysis to those involving C–H bond functionalization and demonstrates the potential of this concept to access Au(I)/Au(III) redox chemistry under mild, redox-neutral conditions.
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spelling pubmed-59507572018-06-01 Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts Tlahuext-Aca, Adrian Hopkinson, Matthew N. Sahoo, Basudev Glorius, Frank Chem Sci Chemistry The arylation of alkyl and aromatic terminal alkynes by a dual gold/photoredox catalytic system is described. Using aryldiazonium salts as readily available aryl sources, a range of diversely-functionalized arylalkynes could be synthesized under mild, base-free reaction conditions using visible light from simple household sources or even sunlight. This process, which exhibits a broad scope and functional group tolerance, expands the range of transformations amenable to dual gold/photoredox catalysis to those involving C–H bond functionalization and demonstrates the potential of this concept to access Au(I)/Au(III) redox chemistry under mild, redox-neutral conditions. Royal Society of Chemistry 2016-01-01 2015-10-08 /pmc/articles/PMC5950757/ /pubmed/29861968 http://dx.doi.org/10.1039/c5sc02583d Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Tlahuext-Aca, Adrian
Hopkinson, Matthew N.
Sahoo, Basudev
Glorius, Frank
Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts
title Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts
title_full Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts
title_fullStr Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts
title_full_unstemmed Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts
title_short Dual gold/photoredox-catalyzed C(sp)–H arylation of terminal alkynes with diazonium salts
title_sort dual gold/photoredox-catalyzed c(sp)–h arylation of terminal alkynes with diazonium salts
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5950757/
https://www.ncbi.nlm.nih.gov/pubmed/29861968
http://dx.doi.org/10.1039/c5sc02583d
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