Dual Nickel- and Photoredox-Catalyzed Reductive Cross-Coupling of Aryl Halides with Dichloromethane via a Radical Process
Wenhao Xu, Purui Zheng, Tao Xu
Abstract
The first catalytic strategy to harness a new chloromethane radical from dichloromethane under dual Ni/photoredox catalytic conditions has been developed. Compared with traditional two-electron reductive process associated with metallic reductants, this method via a single-electron approach can proceed under exceptionally mild conditions (visible light, ambient temperature, no strong base) and exhibits complementary reactivity patterns. It affords a broad scope of many functional groups, including alkenyl, which suffers cyclopropanation in previous routes. The diarylmethane-d2 compounds can be readily available with this transformation.
Topics & Concepts
ChloromethaneChemistryDichloromethaneArylCatalysisAryl radicalCyclopropanationPhotochemistryHalideNickelPhotoredox catalysisReductive eliminationCombinatorial chemistryReactivity (psychology)Catalytic cycleSolventOrganic chemistryAlternative medicineMedicinePhotocatalysisAlkylPathologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsChemical Reactions and Isotopes