title: Intramolecular aminocyanation of alkenes by cooperative palladium/boron catalysis.
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.
authors.affiliation: Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Miyazaki
authors.forename: Naoki
authors.initials: N
authors.lastname: Ohta
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Semba
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Nakao
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D001895:Boron / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014966:Xanthenes / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007211:Indoles; D009570:Nitriles; D010720:Phosphines; D011759:Pyrrolidines; D014966:Xanthenes; D010165:Palladium; C057812:indoline; D001895:Boron; C519861:xantphos