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Intramolecular aminocyanation of alkenes by cooperative palladium/boron catalysis
Yosuke Miyazaki1, Naoki Ohta, Kazuhiko Semba
1Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
Abstract:
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.
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