Issue 15, 2018

Electrochemical oxidative radical oxysulfuration of styrene derivatives with thiols and nucleophilic oxygen sources

Abstract

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.

Graphical abstract: Electrochemical oxidative radical oxysulfuration of styrene derivatives with thiols and nucleophilic oxygen sources

Supplementary files

Article information

Article type
Communication
Submitted
28 Apr 2018
Accepted
20 Jun 2018
First published
22 Jun 2018

Green Chem., 2018,20, 3444-3449

Electrochemical oxidative radical oxysulfuration of styrene derivatives with thiols and nucleophilic oxygen sources

Y. Wang, L. Deng, H. Mei, B. Du, J. Han and Y. Pan, Green Chem., 2018, 20, 3444 DOI: 10.1039/C8GC01337C

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