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Electrochemical Difluoromethylation of Electron-Rich Olefins

Shinan Luan, Thomas Castanheiro, Thomas Poisson

2023Organic Letters36 citationsDOI

Abstract

The electrochemical difluoromethylation of electron-rich olefins (enamides and styrene derivatives) is disclosed. The addition of the electrogenerated difluoromethyl radical from the corresponding sodium sulfinate (i.e., HCF 2 SO 2 Na) to enamides and styrenes in an undivided cell allowed the formation of a large panel of difluoromethylated building blocks in good to excellent yields (42 examples, 23–87% yields). A plausible unified mechanism was suggested according to control experiments and cyclic voltammetry measurements.

Topics & Concepts

ChemistryElectrochemistryCyclic voltammetryStyreneElectronCombinatorial chemistryOrganic chemistryElectrodePhysical chemistryCopolymerPolymerPhysicsQuantum mechanicsFluorine in Organic ChemistryRadical Photochemical ReactionsInorganic Fluorides and Related Compounds
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