Difluoromethyl Radical Triggered Tandem Reaction of <i>N</i>-Allyl Amides to Difluoromethylated β-Amino Alcohols by Photoredox Catalysis
Wen‐Bing Qin, Wei Xiong, Ya-Shi Zhao, Kai-Zhong Fu, Lei Su, Guo‐Kai Liu
Abstract
An elegant tandem reaction process for transferring N-allyl amide into CF2H-β-amino alcohol is described. This approach proceeded smoothly under visible light irradiation in the presence of a 3 mol % Ir complex, exhibiting a broad substrate scope and functional group tolerance, and a variety of CF2H-β-amino alcohols were readily accessed in good to excellent yields under mild conditions. The reliable mechanistic studies revealed that sequential difluoromethyl radical addition/carbocation trap/rearrangement is involved.
Topics & Concepts
ChemistryAlcoholCatalysisFunctional groupTandemAmideCarbocationSubstrate (aquarium)Photoredox catalysisCascade reactionMedicinal chemistryPhotochemistryOrganic chemistryPhotocatalysisComposite materialOceanographyPolymerMaterials scienceGeologyFluorine in Organic ChemistryRadical Photochemical ReactionsChemical Synthesis and Analysis