Intermolecular difunctionalization of alkenes: synthesis of β-hydroxy sulfides

Direct difunctionalization of carbon-carbon double bonds is one of the most powerful tools available for concomitant introduction of two functional groups into olefinic substrates. In this context, vicinal hydroxysulfenylation of unactivated alkenes has emerged as a novel and straightforward strategy for the fabrication of β-hydroxy sulfides, which are extremely valuable starting materials in constructing various natural products, pharmaceuticals, and fine chemicals. The aim of this review is to summarize the most representative and important reports on the preparation of β-hydroxy sulfides through intermolecular hydroxysulfenylation of the corresponding alkenes with special emphasis on the mechanistic features of the reactions.