Electrochemical Difluoromethylation of Electron-Rich Olefins
Shinan Luan, Thomas Castanheiro, Thomas Poisson
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