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Iron-Catalyzed Alkoxyl Radical-Induced C–C Bond Cleavage/<i>gem</i>-Difluoroalkylation Cascade

Tianyu Zhang, Yong Wu, Shuai Liu, Jingqi Tao, Xu Yang, Xueqi Wang, Xin‐Hua Duan, Li‐Na Guo

2023Organic Letters18 citationsDOI

Abstract

-difluoroalkylation cascade is presented. Regulated by the structure of alkoxyl radical precursors, fluorinated distal diketones were synthesized through a ring-opening strategy and difluoroalkylated medium-sized lactones and macrolactones were constructed via a ring-expansion strategy. Both protocols proceeded under mild and redox neutral conditions with a broad substrate scope and good functional group compatibility.

Topics & Concepts

ChemistryCatalysisCascadeCleavage (geology)Alkoxy groupBond cleavageCombinatorial chemistryRing (chemistry)StereochemistryPhotochemistryOrganic chemistryAlkylEngineeringGeotechnical engineeringChromatographyFracture (geology)Fluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Iron-Catalyzed Alkoxyl Radical-Induced C–C Bond Cleavage/<i>gem</i>-Difluoroalkylation Cascade | Litcius