Difluoromethylarylation of α,β-unsaturated amides <i>via</i> a photocatalytic radical smiles rearrangement
Siqi Wei, Siya Le, Ziran Lei, Liejin Zhou, Zuxiao Zhang, William R. Dolbier
Abstract
A photocatalytic Smiles rearrangement, triggered by radical difluoromethylation of conjugated arylsulfonylated amides, was developed to construct both β-difluoromethyl amide and heterocyclic scaffolds selectively. This transformation features mild conditions and broad substrate scope. More importantly, the chemoselectivity of the intermediate amidyl radical could be altered completely by simply changing the light source, along with addition of water to the reaction mixture.
Topics & Concepts
PhotocatalysisConjugated systemChemistryRedoxPhotochemistrySmiles rearrangementMedicinal chemistryOrganic chemistryCatalysisPolymerFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques