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Photoredox/Hydrogen Atom Transfer Cocatalyzed C–H Difluoroallylation of Amides, Ethers, and Alkyl Aldehydes

Yuanqiang Guo, Yifan Wu, Ruiguo Wang, Hongjian Song, Yuxiu Liu, Qingmin Wang

2021Organic Letters94 citationsDOI

Abstract

Herein, we report a method that combines hydrogen atom transfer and photoredox catalysis to achieve the dehydrogenative difluoroallylation of amides, ethers, and alkyl aldehydes. This operationally convenient method transforms a broad scope of substrates into the corresponding gem-difluoroalkenes via the construction of C(sp3)–C(sp3) or C(sp3)–C(sp2) bonds. Excellent functional group compatibility and high selectivity make this method have a wide range of substrate types and render it suitable for late-stage modification of pharmaceutical intermediates.

Topics & Concepts

ChemistryAlkylPhotoredox catalysisHydrogen atomCombinatorial chemistryCatalysisSubstrate (aquarium)Functional groupMoleculeSelectivityOrganic chemistryPhotochemistryPhotocatalysisPolymerOceanographyGeologyFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods