Nickel-Catalyzed Allylic Defluorinative Cross-Electrophile Coupling with Cycloalkyl Silyl Peroxides as the Alkyl Source
Haiyan Dong, Zhiyang Lin, Chuan Wang
Abstract
Herein we demonstrate the first successful application of cycloalkyl silyl peroxides (CSP) as an electrophilic coupling partner in the cross-electrophile coupling reaction. Diverse CSP are efficiently cross-coupled with an array of α-trifluoromethyl alkenes under the catalysis of nickel with the assistance of zinc as the reducing agent. This method allows the use of unstrained CSP as the carbonyl-containing alkyl source in the allylic defluorinative reaction, to access a variety of gem-difluoroalkenes bearing a pendent ketone moiety with high functionality tolerance.
Topics & Concepts
ChemistryElectrophileAllylic rearrangementSilylationKetoneAlkylMoietyTrifluoromethylCatalysisCoupling reactionCombinatorial chemistryOrganic chemistryMedicinal chemistryFluorine in Organic ChemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods