Visible‐Light‐Induced Radical Difluoromethylation of Alkynoates by [bis(Difluoroacetoxy)iodo]benzene to Yield 3‐Difluoromethylated Coumarins
Kui Lu, Ting Zhou, Xiaodong Jia, Wei Peng, Lingyu Lei, Xiaolan Xi, Jiang Liu, Xia Zhao
Abstract
Abstract A visible‐light‐induced radical difluoromethylation of alkynoates using [bis(difluoroacetoxy)iodo]benzene as the CF 2 H radical precursor was developed for the first time. 3‐Difluoromethyl‐substituted coumarins were synthesized via a radical difluoromethylation/cyclization/ester migration cascade. The mild and catalyst‐free conditions, as well as the good functional group tolerance, render this protocol an alternative and green strategy for the synthesis of 3‐difluoromethyl‐substituted coumarins.
Topics & Concepts
ChemistryBenzeneYield (engineering)CatalysisMedicinal chemistryRadical cyclizationCombinatorial chemistryOrganic chemistryPhotochemistryMaterials scienceMetallurgyFluorine in Organic ChemistryRadical Photochemical Reactions