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Selective formation of heteroaryl thioethers via a phosphonium ion coupling reaction.

ABSTRACT: Heteroaryl thioethers, comprised of pyridines and diazines, are an important class of compounds with relevance to medicinal chemistry. Metal-catalyzed cross-couplings and SNAr are traditionally used to form C-S bonds in these systems but are limited by available halogenated precursors. An alternative approach is presented where pyridines and diazines are transformed into heterocyclic phosphonium salts and then C-S bonds are formed by adding thiolate nucleophiles. The process is 4-selective for pyridines, simple to execute and can be used to make derivatives of complex pharmaceuticals.

SUBMITTER: Anderson RG

PROVIDER: S-EPMC6252084 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Selective formation of heteroaryl thioethers via a phosphonium ion coupling reaction.

Anderson Ryan G RG Jett Brianna M BM McNally Andrew A

Tetrahedron 20171221 25

Heteroaryl thioethers, comprised of pyridines and diazines, are an important class of compounds with relevance to medicinal chemistry. Metal-catalyzed cross-couplings and S<sub>N</sub>Ar are traditionally used to form C-S bonds in these systems but are limited by available halogenated precursors. An alternative approach is presented where pyridines and diazines are transformed into heterocyclic phosphonium salts and then C-S bonds are formed by adding thiolate nucleophiles. The process is 4-sele ...[more]

PMID: 30479455

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