Nickel-catalyzed insertions of vinylidenes into Si–H bonds
Sourish Biswas, Sudipta Pal, Christopher Uyeda
Abstract
A nickel-catalyzed reductive cyclization of 1,1-dichloroalkenyl silanes is reported. The products of this reaction are unsaturated five- or six-membered silacycles. Intermolecular variants are also described, providing access to trisubstituted vinyl silanes that are not accessible by alkyne hydrosilylation or sila-Heck-type processes. A variety of silanes can be utilized, including those that serve as nucleophilic partners in Hiyama cross-coupling reactions. Mechanistic studies using deuterium-labelled silanes are described.
Topics & Concepts
SilanesHydrosilylationChemistryCatalysisNickelNucleophileIntermolecular forceAlkyneOrganic chemistryPolymer chemistryCombinatorial chemistrySilaneMoleculeCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistry