Chiral Selenide-Catalyzed, Highly Regio- and Enantioselective Intermolecular Thioarylation of Alkenes with Phenols

Abstract

Enantioselective electrophilic three-component thioarylation of alkenes by chiral selenide catalysis with free phenols as arylating sources is disclosed. A variety of chiral phenols were achieved in high regio-, enantio-, and diastereoselectivities. Mechanistic studies revealed that this transformation went through carbon nucleophilic attack to give the products rather than the process of intramolecular rearrangement of phenolic ether intermediates. The application of this organocatalytic method in the alkylation of methoxy-substituted benzenes elucidated its generality.