Electrochemical oxidative radical oxysulfuration of styrene derivatives with thiols and nucleophilic oxygen sourcesElectronic supplementary information (ESI) available: General reaction procedures, characterization data, and copies of NMR spectra. See DOI: 10.1039/c8gc01337c

• Main Authors: Wang, Yang, Deng, Lingling, Mei, Haibo, Du, Bingnan, Han, Jianlin, Pan, Yi
• Format: Article
• Language: English
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c8gc01337c

Oxydifunctionalization of olefins represents a powerful tool and yet poses a challenging task. Previous methods have usually required a stoichiometric amount of a strong oxidant and an expensive transition-metal catalyst. This work describes the first example of the electrochemical oxysulfuration reaction of olefins with thiols and nucleophilic oxygen sources. This electrochemical difunctionalization reaction is conducted under catalyst- and oxidant-free conditions, and shows good substrate generality, affording thio-substituted alcohols, ethers and γ-lactones in good chemical yields and with excellent regioselectivities. This work represents a new and green strategy for the difunctionalization of olefins, and also provides a complementary and highly valuable prospect for current methodologies for the synthesis of thio-substituted compounds. The first example of the electrochemical oxysulfuration reaction of alkenes with thiols and nucleophilic oxygen sources has been reported.