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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...

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Autores principales: Merad, Jérémy, Matyašovský, Ján, Stopka, Tobias, Brutiu, Bogdan R., Pinto, Alexandre, Drescher, Martina, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
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.
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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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