Issue 22, 2021

Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols

Abstract

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.

Graphical abstract: Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols

Supplementary files

Article information

Article type
Edge Article
Submitted
20 mar 2021
Accepted
28 apr 2021
First published
06 maj 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 7770-7774

Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols

J. Merad, J. Matyašovský, T. Stopka, B. R. Brutiu, A. Pinto, M. Drescher and N. Maulide, Chem. Sci., 2021, 12, 7770 DOI: 10.1039/D1SC01602D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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