Electrochemically Promoted Oxydifluoroethylation of Alkenes for the Synthesis of Difluoroethylated Benzoxazines and Lactones
Yunfei Tian, Luping Zheng, Yuting Yang, Jiayi Liu, Zihan Jing, Zejiang Li, Weijun Fu
Abstract
Abstract An electrochemical oxydifluoroethylation of alkenes involving the anodic oxidative generation of MeCF 2 radical has been achieved, which enabled to construct diversified difluoroethylated benzoxazines and lactones in 35–87% yields. Moreover, the developed protocol was also extended to the synthesis of cyclopropyldifluoromethylated benzoxazines. Detailed mechanistic studies indicated the reaction underwent a radical process concerned with tandem C−CF 2 R and C−O bond formation.
Topics & Concepts
ChemistryTandemElectrochemistryCombinatorial chemistryOrganic chemistryComposite materialPhysical chemistryMaterials scienceElectrodeFluorine in Organic ChemistryRadical Photochemical Reactions