Photocatalytic Remote Oxyfluoroalkylation of Heteroalkynes: Regio-, Stereo-, and Site-Selective Access to Complex Fluoroalkylated (<i>Z</i>)-Alkenes
Tianbo Shang, Junhua Zhang, Yan Zhang, Fang Zhang, Xinsheng Li, Gangguo Zhu
Abstract
A visible-light-induced remote oxyfluoroalkylation, including ketofluoroalkylation and hydroxytrifluoromethylation, of heteroalkynes is developed with dimethyl sulfoxide (DMSO) and H2O as the oxygen source, respectively. It provides a facile access to complex fluoroalkylated (Z)-alkenes in satisfactory yields with excellent regio-, stereo-, and site-selectivity. The reaction involves an uncommon vinyl radical-induced intermolecular C(sp3)–H functionalization, thus offering a good platform for the development of remote difunctionalization of alkynes.
Topics & Concepts
ChemistryPhotocatalysisPhotochemistryOrganic chemistryCatalysisFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods