Cargando…
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...
Autores principales: | , , , , , |
---|---|
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 |
_version_ | 1783447098784481280 |
---|---|
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. |
format | Online Article Text |
id | pubmed-6714600 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT changrui visiblelightmediateddirectcharoylationandalkylationofheteroarenes AT fangjie visiblelightmediateddirectcharoylationandalkylationofheteroarenes AT chenjianqiang visiblelightmediateddirectcharoylationandalkylationofheteroarenes AT liudan visiblelightmediateddirectcharoylationandalkylationofheteroarenes AT xuguoqiang visiblelightmediateddirectcharoylationandalkylationofheteroarenes AT xupengfei visiblelightmediateddirectcharoylationandalkylationofheteroarenes |