Dual Photoredox/Palladium-Catalyzed C–H Acylation of 2-Arylpyridines with Oxime Esters
Xiaopeng Liu, Jia‐Rong Chen, Bin‐Qing He, Yuan Gao, Peng‐Zi Wang, Hong Wu, Hongbin Zhou
Abstract
An unprecedented dual photoredox/palladium-catalyzed iminyl-radical-mediated C–C bond cleavage and directed ortho C–H acylation of 2-arylpyridines by using oxime esters is described. Oxime esters can serve as efficient acyl sources through formation of the corresponding acyl radicals by photoredox-catalyzed iminyl-radical-mediated C–C bond cleavage. This redox-neutral protocol features excellent regioselectivity, a broad substrate scope, and good functional-group tolerance with respect to both components, giving a broad range of aryl ketones with generally good yields.
Topics & Concepts
ChemistryOximeAcylationPalladiumRegioselectivityBond cleavageFunctional groupArylRadicalCatalysisCleavage (geology)Medicinal chemistryCombinatorial chemistryOrganic chemistryPhotochemistryFracture (geology)Geotechnical engineeringEngineeringAlkylPolymerCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques