Litcius/Paper detail

Cooperative NHC/Photoredox Catalysis: Three Component Radical Coupling of Aroyl Fluorides, Styrenes and Alcohols

Nadine Döben, Jannik Reimler, Armido Studer

2022Advanced Synthesis & Catalysis36 citationsDOI

Abstract

Abstract Cooperative NHC/photoredox catalysis has emerged as an important research field in recent years. Herein, the use of tertiary alcohols as alkyl radical precursors to perform three component radical coupling with styrenes and aroyl fluorides for the preparation of α‐arylated alkyl aryl ketones is described. Reaction of an aroyl fluoride with the NHC catalyst provides an acyl azolium ion that can be reduced by the photoredox catalyst to the corresponding ketyl radical anion. Oxidatively generated C‐radicals derived from the alcohol add to the styrene derivative and subsequent cross coupling of the adduct radical with the ketyl radical delivers after NHC fragmentation the targeted ketone. magnified image

Topics & Concepts

KetylChemistryPhotoredox catalysisRadicalAdductAlkylCatalysisArylKetonePhotochemistryAlcoholStyreneOrganic chemistryMedicinal chemistryPolymerCopolymerPhotocatalysisN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization MethodsRadical Photochemical Reactions