Catalyzing the Hydrodefluorination of CF<sub>3</sub>-Substituted Alkenes by PhSiH<sub>3</sub>. H• Transfer from a Nickel Hydride
Chengbo Yao, Shuai Wang, Jack R. Norton, Matthew J. Hammond
Abstract
The hydrodefluorination of CF3-substituted alkenes can be catalyzed by a nickel(II) hydride bearing a pincer ligand. The catalyst loading can be as low as 1 mol%. gem-Difluoroalkenes containing a number of functional groups can be formed in good to excellent yields by a radical mechanism initiated by H• transfer from the nickel hydride. The relative reactivity of various substrates supports the proposed mechanism, as does a TEMPO trapping experiment.
Topics & Concepts
ChemistryHydrideNickelPincer ligandReactivity (psychology)CatalysisPincer movementLigand (biochemistry)PhotochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryMetalPathologyMedicineReceptorBiochemistryAlternative medicineFluorine in Organic ChemistryInorganic Fluorides and Related Compounds