Electrochemical Difunctionalization of Alkenes

Abstract

AbstractThe electrochemical alkene difunctionalization reaction has become a powerful and sustainable tool for the efficient construction of vicinal difunctionalized structures in organic synthesis. Since only electrons are used as the redox agents, electrochemical alkene difunctionalization avoids the need for additional redox catalysts, metal catalysts, or chemical oxidants and does not generate chemical waste. Herein we summarize the latest contributions in the electrochemical difunctionalization of alkenes over the last 3–4 years. We discuss in detail the reaction features, scope, limitations, and mechanistic rationalizations of three categories of alkene difunctionalization methods: (1) electrochemical alkene difunctionalization terminated by nucleophiles, (2) electrochemical difunctionalization of alkenes terminated by radicals, and (3) electrochemical alkene difunctionalization terminated by functionality migration.1 Introduction2 Electrochemical Alkene Difunctionalization Terminated by Nucleophiles2.1 Sulfonylative Difunctionalization of Alkenes2.2 Sulfurizative/Sulfoxidative Difunctionalization of Alkenes2.3 Azidotetrazolation of Alkenes2.4 Trifluoromethylative Difunctionalization of Alkenes2.5 Diarylation of Alkenes3 Electrochemical Difunctionalization of Alkenes Terminated by Radicals3.1 Direct Radical-Coupling-Enabled Alkene Difunctionalization3.2 Metal-Mediated Radical Transfer Coupling Enabled Alkene Difunctionalization3.3 Metalloid-Mediated Radical Transfer Coupling Enabled Alkene Difunctionalization4 Electrochemical Alkene Difunctionalization Terminated by Functionality Migration5 Summary and Outlook