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Visible-Light-Induced Deoxygenation/Defluorination Protocol for Synthesis of γ,γ-Difluoroallylic Ketones

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

2020Organic Letters135 citationsDOI

Abstract

Herein, we describe an efficient, practical photocatalytic deoxygenation/defluorination protocol for the synthesis of γ,γ-difluoroallylic ketones from commercially available aromatic carboxylic acids, triphenylphosphine, and α-trifluoromethyl alkenes. The protocol has good functional group tolerance and a broad substrate scope. Using this method, we accomplished the late-stage functionalization of several bioactive molecules.

Topics & Concepts

DeoxygenationChemistryTrifluoromethylSubstrate (aquarium)Functional groupTriphenylphosphineCombinatorial chemistryPhotocatalysisSurface modificationProtocol (science)Organic chemistryCatalysisMedicinePathologyAlkylOceanographyGeologyPhysical chemistryAlternative medicinePolymerFluorine in Organic ChemistryChemical Synthesis and AnalysisRadical Photochemical Reactions