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.

Citation

Yosuke Miyazaki, Naoki Ohta, Kazuhiko Semba, Yoshiaki Nakao. Intramolecular aminocyanation of alkenes by cooperative palladium/boron catalysis. Journal of the American Chemical Society. 2014 Mar 12;136(10):3732-5

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PMID: 24580141

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