Benzylic C–H heteroarylation of<i>N</i>-(benzyloxy)phthalimides with cyanopyridines enabled by photoredox 1,2-hydrogen atom transfer
Long‐Jin Zhong, Hongyu Wang, Xuan‐Hui Ouyang, Jin‐Heng Li, Delie An
Abstract
A visible light initiated α-C(sp3)-H arylation of N-(benzyloxy)phthalimides with cyanopyridines for the construction of highly valuable pyridinyl-containing diarylmethanols, including bioactive motif-based analogues, is reported. This method enables arylation of the C(sp3)-H bonds adjacent to an oxygen atom through alkoxy radical formation by O-N bond cleavage, 1,2-hydrogen atom transfer (HAT), arylation and C-CN bond cleavage cascades, and offers a means to exploit 1,2-HAT modes to incorporate functional groups for constructing functionalized alcohols.
Topics & Concepts
PhthalimidesHydrogen atomChemistryMedicinal chemistryPhotoredox catalysisAtom (system on chip)HydrogenTransfer (computing)PhotochemistryPhthalimideOrganic chemistryCatalysisPhotocatalysisComputer scienceGroup (periodic table)Parallel computingCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSynthesis and Catalytic Reactions