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Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols
Isothiouronium salts are easily accessible and stable compounds. Herein, we report their use as versatile deoxasulfenylating agents enabling a stereoselective, thiol-free protocol for synthesis of thioethers from alcohols. The method is simple, scalable and tolerates a broad range of functional grou...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8188487/ https://www.ncbi.nlm.nih.gov/pubmed/34168830 http://dx.doi.org/10.1039/d1sc01602d |
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author | Merad, Jérémy Matyašovský, Ján Stopka, Tobias Brutiu, Bogdan R. Pinto, Alexandre Drescher, Martina Maulide, Nuno |
author_facet | Merad, Jérémy Matyašovský, Ján Stopka, Tobias Brutiu, Bogdan R. Pinto, Alexandre Drescher, Martina Maulide, Nuno |
author_sort | Merad, Jérémy |
collection | PubMed |
description | Isothiouronium salts are easily accessible and stable compounds. Herein, we report their use as versatile deoxasulfenylating agents enabling a stereoselective, thiol-free protocol for synthesis of thioethers from alcohols. The method is simple, scalable and tolerates a broad range of functional groups otherwise incompatible with other methods. Late-stage modification of several pharmaceuticals provides access to multiple analogues of biologically relevant molecules. Performed experiments give insight into the reaction mechanism. |
format | Online Article Text |
id | pubmed-8188487 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81884872021-06-23 Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols Merad, Jérémy Matyašovský, Ján Stopka, Tobias Brutiu, Bogdan R. Pinto, Alexandre Drescher, Martina Maulide, Nuno Chem Sci Chemistry Isothiouronium salts are easily accessible and stable compounds. Herein, we report their use as versatile deoxasulfenylating agents enabling a stereoselective, thiol-free protocol for synthesis of thioethers from alcohols. The method is simple, scalable and tolerates a broad range of functional groups otherwise incompatible with other methods. Late-stage modification of several pharmaceuticals provides access to multiple analogues of biologically relevant molecules. Performed experiments give insight into the reaction mechanism. The Royal Society of Chemistry 2021-05-06 /pmc/articles/PMC8188487/ /pubmed/34168830 http://dx.doi.org/10.1039/d1sc01602d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Merad, Jérémy Matyašovský, Ján Stopka, Tobias Brutiu, Bogdan R. Pinto, Alexandre Drescher, Martina Maulide, Nuno Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols |
title | Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols |
title_full | Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols |
title_fullStr | Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols |
title_full_unstemmed | Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols |
title_short | Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols |
title_sort | stable and easily available sulfide surrogates allow a stereoselective activation of alcohols |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8188487/ https://www.ncbi.nlm.nih.gov/pubmed/34168830 http://dx.doi.org/10.1039/d1sc01602d |
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