Electrochemical Atom Transfer Radical Addition of Polychloroalkanes to Olefins Promoted by 4,<scp>4‐Di</scp>‐<i>tert</i>‐butyl Bipyridine
Fei Lian, Fei‐Xian Luo, Meng Wang, Kun Xu, Cheng‐Chu Zeng
Abstract
Comprehensive Summary A new electrochemical strategy for the atom transfer radical addition (ATRA) of polychloroalkanes across olefins has been realized by the synergism of paired electrolysis and halogen bonding activation. Notably, readily accessible 4,4‐di‐ tert ‐butyl bipyridine (dtbpy), acting as a halogen bonding acceptor, shifted the reduction potential of C—Cl bonds positively by 110 mV. The decreased operating potential leads to a wide substrate scope and excellent functional group compatibility. A diverse array of terminal and internal alkenes such as (hetero)aryl olefins, unactive aliphatic olefins, and natural products and drugs‐derived olefins were well compatible.
Topics & Concepts
ChemistryElectrochemistryHalogen bondAryl radicalHalogenAcceptorElectrolysisArylBipyridineCombinatorial chemistryPhotochemistryMedicinal chemistryPolymer chemistryOrganic chemistryElectrodePhysical chemistryAlkylCrystal structureElectrolyteCondensed matter physicsPhysicsRadical Photochemical ReactionsCO2 Reduction Techniques and CatalystsCatalytic C–H Functionalization Methods