Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives

[Image: see text] Herein, we report a straightforward practical method for efficiently obtaining a diverse range of thiophosphonium salts. This method involves the direct coupling of commercially available thiols and aldehydes with Ph(3)P and TfOH. The setup is simple and carried out in a metal-free...

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Autores principales: Hazra, Gurupada, Masarwa, Ahmad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476193/
https://www.ncbi.nlm.nih.gov/pubmed/37610079
http://dx.doi.org/10.1021/acs.orglett.3c02422
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author Hazra, Gurupada
Masarwa, Ahmad
author_facet Hazra, Gurupada
Masarwa, Ahmad
author_sort Hazra, Gurupada
collection PubMed
description [Image: see text] Herein, we report a straightforward practical method for efficiently obtaining a diverse range of thiophosphonium salts. This method involves the direct coupling of commercially available thiols and aldehydes with Ph(3)P and TfOH. The setup is simple and carried out in a metal-free manner. The synthetic utility of these salts is demonstrated through various examples of C–P bond functionalizations, enabling the synthesis of thioether, deuterated thioether, thioester, and dithioester derivatives. These products, which serve as valuable building blocks, are obtained in high yields.
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spelling pubmed-104761932023-09-05 Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives Hazra, Gurupada Masarwa, Ahmad Org Lett [Image: see text] Herein, we report a straightforward practical method for efficiently obtaining a diverse range of thiophosphonium salts. This method involves the direct coupling of commercially available thiols and aldehydes with Ph(3)P and TfOH. The setup is simple and carried out in a metal-free manner. The synthetic utility of these salts is demonstrated through various examples of C–P bond functionalizations, enabling the synthesis of thioether, deuterated thioether, thioester, and dithioester derivatives. These products, which serve as valuable building blocks, are obtained in high yields. American Chemical Society 2023-08-23 /pmc/articles/PMC10476193/ /pubmed/37610079 http://dx.doi.org/10.1021/acs.orglett.3c02422 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Hazra, Gurupada
Masarwa, Ahmad
Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives
title Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives
title_full Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives
title_fullStr Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives
title_full_unstemmed Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives
title_short Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives
title_sort synthesis and functionalization of thiophosphonium salts: a divergent approach to access thioether, thioester, and dithioester derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476193/
https://www.ncbi.nlm.nih.gov/pubmed/37610079
http://dx.doi.org/10.1021/acs.orglett.3c02422
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