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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.

SUBMITTER: Merad J

PROVIDER: S-EPMC8188487 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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

Merad Jérémy J Matyašovský Ján J Stopka Tobias T Brutiu Bogdan R BR Pinto Alexandre A Drescher Martina M Maulide Nuno N

Chemical science 20210506 22

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 in ...[more]

PMID: 34168830

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