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Electroreductive Carbofunctionalization of Alkenes with Alkyl Bromides via a Radical-Polar Crossover Mechanism

Wen Zhang and Song Lin*

*Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14850, United States, Email:

W. Zhang, S. Lin, J. Am. Chem. Soc., 2020, 142, 19844-19849.

DOI: 10.1021/jacs.0c08532 (free Supporting Information)

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An electrochemical reductive functionalization of alkenes with strategic choice of reagents and reaction conditions enables an addition of two distinct electrophiles in a highly chemo- and regioselective fashion. Intermolecular carboformylation, anti-Markovnikov hydroalkylation, and carbocarboxylation of alkenes can be achieved via electroreductive generation of alkyl radical and carbanion intermediates.

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Key Words

formylation, alkylations, multicomponent reactions, electrochemistry

ID: J48-Y2020