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Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation

[Image: see text] The visible-light-promoted catalyst-free condition has been demonstrated for self- and cross-coupling reactions of thiols in an ambient atmosphere. Further, synthesis of β-hydroxysulfides is accomplished under very mild conditions involving the formation of an electron donor–accept...

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Autores principales: Das, Anupam, Thomas, K. R. Justin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10210280/
https://www.ncbi.nlm.nih.gov/pubmed/37251145
http://dx.doi.org/10.1021/acsomega.3c02070
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author Das, Anupam
Thomas, K. R. Justin
author_facet Das, Anupam
Thomas, K. R. Justin
author_sort Das, Anupam
collection PubMed
description [Image: see text] The visible-light-promoted catalyst-free condition has been demonstrated for self- and cross-coupling reactions of thiols in an ambient atmosphere. Further, synthesis of β-hydroxysulfides is accomplished under very mild conditions involving the formation of an electron donor–acceptor (EDA) complex between a disulfide and an alkene. However, the direct reaction of thiol with alkene via the formation of a thiol–oxygen co-oxidation (TOCO) complex failed to produce the desired compounds in high yields. The protocol was successful with several aryl and alkyl thiols for the formation of disulfides. However, the formation of β-hydroxysulfides required an aromatic unit on the disulfide fragment, which supports the formation of the EDA complex during the course of the reaction. The approaches presented in this paper for the coupling reaction of thiols and the synthesis of β-hydroxysulfides are unique and do not require toxic organic or metal catalysts.
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spelling pubmed-102102802023-05-26 Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation Das, Anupam Thomas, K. R. Justin ACS Omega [Image: see text] The visible-light-promoted catalyst-free condition has been demonstrated for self- and cross-coupling reactions of thiols in an ambient atmosphere. Further, synthesis of β-hydroxysulfides is accomplished under very mild conditions involving the formation of an electron donor–acceptor (EDA) complex between a disulfide and an alkene. However, the direct reaction of thiol with alkene via the formation of a thiol–oxygen co-oxidation (TOCO) complex failed to produce the desired compounds in high yields. The protocol was successful with several aryl and alkyl thiols for the formation of disulfides. However, the formation of β-hydroxysulfides required an aromatic unit on the disulfide fragment, which supports the formation of the EDA complex during the course of the reaction. The approaches presented in this paper for the coupling reaction of thiols and the synthesis of β-hydroxysulfides are unique and do not require toxic organic or metal catalysts. American Chemical Society 2023-05-08 /pmc/articles/PMC10210280/ /pubmed/37251145 http://dx.doi.org/10.1021/acsomega.3c02070 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Das, Anupam
Thomas, K. R. Justin
Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation
title Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation
title_full Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation
title_fullStr Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation
title_full_unstemmed Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation
title_short Tuning Selectivity in the Visible-Light-Promoted Coupling of Thiols with Alkenes by EDA vs TOCO Complex Formation
title_sort tuning selectivity in the visible-light-promoted coupling of thiols with alkenes by eda vs toco complex formation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10210280/
https://www.ncbi.nlm.nih.gov/pubmed/37251145
http://dx.doi.org/10.1021/acsomega.3c02070
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