title: Cu-Catalyzed Cyanation of Arylboronic Acids with Acetonitrile: A Dual Role of TEMPO.
abstract: The cyanation of arylboronic acids by using acetonitrile as the "CN" source has been achieved under a Cu(cat.)/TEMPO system (TEMPO=2,2,6,6-tetramethylpiperidine N-oxide). The broad substrate scope includes a variety of electron-rich and electron-poor arylboronic acids, which react well to give the cyanated products in high to excellent yields. Mechanistic studies reveal that TEMPO-CH2 CN, generated in situ, is an active cyanating reagent, and shows high reactivity for the formation of the CN(-) moiety. Moreover, TEMPO acts as a cheap oxidant to enable the reaction to be catalytic in copper.
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 (P.R. China), Fax: (+86) 21-54741297.
authors.forename: Yamin
authors.initials: Y
authors.lastname: Zhu
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 (P.R. China), Fax: (+86) 21-54741297.
authors.forename: Linyi
authors.initials: L
authors.lastname: Li
authors.affiliation: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 (P.R. China), Fax: (+86) 21-54741297. shenzengming@sjtu.edu.cn.
authors.forename: Zengming
authors.initials: Z
authors.lastname: Shen
keywords: CC activation; TEMPO; arylboronic acid; copper; cyanides