Intramolecular Aminocyanation of Alkenes by Cooperative Palladium/Boron Catalysis

A cooperative palladium/triorganoboron
catalyst to accomplish the
intramolecular aminocyanation of alkenes through the cleavage of N–CN
bonds is reported. 4,5-Bis­(diphenylphosphino)-9,9-dimethylxanthene
(Xantphos) is found to be crucial as a ligand for palladium to effectively
catalyze the transformation with high chemo- and regioselectivity.
A range of substituted indolines and pyrrolidines with both tetra-
or trisubstituted carbon and cyano functionalities are readily furnished
by the newly developed cyanofunctionalization reaction. A preliminary
example of enantioselective aminocyanation is also described.