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Visible Light-Mediated Direct C–H Aroylation and Alkylation of Heteroarenes

[Image: see text] Herein, we describe the photocatalytic generation of nucleophilic aroyl radicals from simple aroyl chlorides as a universal and efficient cross-coupling strategy for the direct aroylation of heteroarenes. Furthermore, visible light-mediated direct alkylation of heteroarenes has als...

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Autores principales: Chang, Rui, Fang, Jie, Chen, Jian-Qiang, Liu, Dan, Xu, Guo-Qiang, Xu, Peng-Fei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714600/
https://www.ncbi.nlm.nih.gov/pubmed/31497720
http://dx.doi.org/10.1021/acsomega.9b01674
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author Chang, Rui
Fang, Jie
Chen, Jian-Qiang
Liu, Dan
Xu, Guo-Qiang
Xu, Peng-Fei
author_facet Chang, Rui
Fang, Jie
Chen, Jian-Qiang
Liu, Dan
Xu, Guo-Qiang
Xu, Peng-Fei
author_sort Chang, Rui
collection PubMed
description [Image: see text] Herein, we describe the photocatalytic generation of nucleophilic aroyl radicals from simple aroyl chlorides as a universal and efficient cross-coupling strategy for the direct aroylation of heteroarenes. Furthermore, visible light-mediated direct alkylation of heteroarenes has also been achieved using unactivated bromoalkanes as radical precursors. These two strategies feature high functional group tolerance, exclusive regioselectivity for reaction at the more electrophilic position of heteroarenes, easily accessible substrates, and mild reaction conditions. Moreover, mechanism studies of two reactions are carried out to support our hypotheses.
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spelling pubmed-67146002019-09-06 Visible Light-Mediated Direct C–H Aroylation and Alkylation of Heteroarenes Chang, Rui Fang, Jie Chen, Jian-Qiang Liu, Dan Xu, Guo-Qiang Xu, Peng-Fei ACS Omega [Image: see text] Herein, we describe the photocatalytic generation of nucleophilic aroyl radicals from simple aroyl chlorides as a universal and efficient cross-coupling strategy for the direct aroylation of heteroarenes. Furthermore, visible light-mediated direct alkylation of heteroarenes has also been achieved using unactivated bromoalkanes as radical precursors. These two strategies feature high functional group tolerance, exclusive regioselectivity for reaction at the more electrophilic position of heteroarenes, easily accessible substrates, and mild reaction conditions. Moreover, mechanism studies of two reactions are carried out to support our hypotheses. American Chemical Society 2019-08-14 /pmc/articles/PMC6714600/ /pubmed/31497720 http://dx.doi.org/10.1021/acsomega.9b01674 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Chang, Rui
Fang, Jie
Chen, Jian-Qiang
Liu, Dan
Xu, Guo-Qiang
Xu, Peng-Fei
Visible Light-Mediated Direct C–H Aroylation and Alkylation of Heteroarenes
title Visible Light-Mediated Direct C–H Aroylation and Alkylation of Heteroarenes
title_full Visible Light-Mediated Direct C–H Aroylation and Alkylation of Heteroarenes
title_fullStr Visible Light-Mediated Direct C–H Aroylation and Alkylation of Heteroarenes
title_full_unstemmed Visible Light-Mediated Direct C–H Aroylation and Alkylation of Heteroarenes
title_short Visible Light-Mediated Direct C–H Aroylation and Alkylation of Heteroarenes
title_sort visible light-mediated direct c–h aroylation and alkylation of heteroarenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714600/
https://www.ncbi.nlm.nih.gov/pubmed/31497720
http://dx.doi.org/10.1021/acsomega.9b01674
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