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Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes

Regioselective difunctionalization of alkenes has attracted significant attention from synthetic chemists and has the advantage of introducing diverse functional groups into vicinal carbons of common alkene moieties in a single operation. Herein, we report an unprecedented intermolecular atom transf...

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Detalles Bibliográficos
Autores principales: Li, Haoyu, Shan, Cuicui, Tung, Chen-Ho, Xu, Zhenghu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5431698/
https://www.ncbi.nlm.nih.gov/pubmed/28553495
http://dx.doi.org/10.1039/c6sc05093j
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author Li, Haoyu
Shan, Cuicui
Tung, Chen-Ho
Xu, Zhenghu
author_facet Li, Haoyu
Shan, Cuicui
Tung, Chen-Ho
Xu, Zhenghu
author_sort Li, Haoyu
collection PubMed
description Regioselective difunctionalization of alkenes has attracted significant attention from synthetic chemists and has the advantage of introducing diverse functional groups into vicinal carbons of common alkene moieties in a single operation. Herein, we report an unprecedented intermolecular atom transfer thiosulfonylation reaction of alkenes by combining gold catalysis and visible-light photoredox catalysis. A trifluoromethylthio group (SCF(3)) and other functionalized thio groups together with a sulfonyl group were regioselectively introduced into alkenes in the most atom economical manner. A detailed mechanism study indicated that a synergistic combination of gold catalysis and photoredox catalysis is crucial for this reaction.
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spelling pubmed-54316982017-05-26 Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes Li, Haoyu Shan, Cuicui Tung, Chen-Ho Xu, Zhenghu Chem Sci Chemistry Regioselective difunctionalization of alkenes has attracted significant attention from synthetic chemists and has the advantage of introducing diverse functional groups into vicinal carbons of common alkene moieties in a single operation. Herein, we report an unprecedented intermolecular atom transfer thiosulfonylation reaction of alkenes by combining gold catalysis and visible-light photoredox catalysis. A trifluoromethylthio group (SCF(3)) and other functionalized thio groups together with a sulfonyl group were regioselectively introduced into alkenes in the most atom economical manner. A detailed mechanism study indicated that a synergistic combination of gold catalysis and photoredox catalysis is crucial for this reaction. Royal Society of Chemistry 2017-04-01 2017-01-04 /pmc/articles/PMC5431698/ /pubmed/28553495 http://dx.doi.org/10.1039/c6sc05093j Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Li, Haoyu
Shan, Cuicui
Tung, Chen-Ho
Xu, Zhenghu
Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes
title Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes
title_full Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes
title_fullStr Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes
title_full_unstemmed Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes
title_short Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes
title_sort dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5431698/
https://www.ncbi.nlm.nih.gov/pubmed/28553495
http://dx.doi.org/10.1039/c6sc05093j
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