title: Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β-Ketonitrile Derivatives.
abstract: The highly efficient electrophilic cyanation of boron enolates using readily available cyanating reagents, N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) and p-toluenesulfonyl cyanide (TsCN), is reported. Various β-ketonitriles were prepared by this new protocol, which has a remarkably broad substrate scope compared to existing methods. The present method also allowed efficient synthesis of β-ketonitriles containing a quaternary α-carbon center. In addition, a preliminary result with the use of a chiral boron enolate for the enantioselective cyanation reaction is described.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan. kiyokawa@chem.eng.osaka-u.ac.jp.
authors.forename: Kensuke
authors.initials: K
authors.lastname: Kiyokawa
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan.
authors.forename: Takaya
authors.initials: T
authors.lastname: Nagata
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka, 565-0871, Japan. minakata@chem.eng.osaka-u.ac.jp.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Minakata
keywords: boron; cyanation; nucleophilic addition; reaction mechanisms; synthetic methods