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Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO(2)

The selective oxidation of sulfides into sulfoxides receives much attention due to industrial and biological applications. However, the realization of this reaction with molecular oxygen at room temperature, which is of importance towards green and sustainable chemistry, remains challenging. Herein,...

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Detalles Bibliográficos
Autores principales: Lang, Xianjun, Hao, Wei, Leow, Wan Ru, Li, Shuzhou, Zhao, Jincai, Chen, Xiaodong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5664354/
https://www.ncbi.nlm.nih.gov/pubmed/29142727
http://dx.doi.org/10.1039/c5sc01813g
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author Lang, Xianjun
Hao, Wei
Leow, Wan Ru
Li, Shuzhou
Zhao, Jincai
Chen, Xiaodong
author_facet Lang, Xianjun
Hao, Wei
Leow, Wan Ru
Li, Shuzhou
Zhao, Jincai
Chen, Xiaodong
author_sort Lang, Xianjun
collection PubMed
description The selective oxidation of sulfides into sulfoxides receives much attention due to industrial and biological applications. However, the realization of this reaction with molecular oxygen at room temperature, which is of importance towards green and sustainable chemistry, remains challenging. Herein, we develop a strategy to achieve the aerobic oxidation of sulfides into sulfoxides by exploring the synergy between a tertiary amine and titanium dioxide via visible-light photoredox catalysis. Specifically, titanium dioxide can interact with triethylamine (TEA) to form a visible-light harvesting surface complex, preluding the ensuing selective redox reaction. Moreover, TEA, whose stability was demonstrated by a turnover number of 32, plays a critical role as a redox mediator by shuttling electrons during the oxidation of sulfide. This work suggests that the addition of a redox mediator is highly functional in establishing visible-light-induced reactions via heterogeneous photoredox catalysis.
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spelling pubmed-56643542017-11-15 Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO(2) Lang, Xianjun Hao, Wei Leow, Wan Ru Li, Shuzhou Zhao, Jincai Chen, Xiaodong Chem Sci Chemistry The selective oxidation of sulfides into sulfoxides receives much attention due to industrial and biological applications. However, the realization of this reaction with molecular oxygen at room temperature, which is of importance towards green and sustainable chemistry, remains challenging. Herein, we develop a strategy to achieve the aerobic oxidation of sulfides into sulfoxides by exploring the synergy between a tertiary amine and titanium dioxide via visible-light photoredox catalysis. Specifically, titanium dioxide can interact with triethylamine (TEA) to form a visible-light harvesting surface complex, preluding the ensuing selective redox reaction. Moreover, TEA, whose stability was demonstrated by a turnover number of 32, plays a critical role as a redox mediator by shuttling electrons during the oxidation of sulfide. This work suggests that the addition of a redox mediator is highly functional in establishing visible-light-induced reactions via heterogeneous photoredox catalysis. Royal Society of Chemistry 2015-08-01 2015-06-09 /pmc/articles/PMC5664354/ /pubmed/29142727 http://dx.doi.org/10.1039/c5sc01813g Text en This journal is © The Royal Society of Chemistry 2015 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
Lang, Xianjun
Hao, Wei
Leow, Wan Ru
Li, Shuzhou
Zhao, Jincai
Chen, Xiaodong
Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO(2)
title Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO(2)
title_full Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO(2)
title_fullStr Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO(2)
title_full_unstemmed Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO(2)
title_short Tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on TiO(2)
title_sort tertiary amine mediated aerobic oxidation of sulfides into sulfoxides by visible-light photoredox catalysis on tio(2)
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5664354/
https://www.ncbi.nlm.nih.gov/pubmed/29142727
http://dx.doi.org/10.1039/c5sc01813g
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