title: Radical-mediated divergent cyclization of benzamides toward perfluorinated or cyanated isoquinolinediones.
abstract: A simple and efficient copper-controlled divergent cyclization of benzamides, which leads to perfluorinated or cyanated isoquinolinediones, is developed. In the presence of AIBN, methacryloyl benzamides with perfluoroalkyl iodides undergo cascade radical addition/cyclization to afford perfluoroinated isoquinolinediones as the major product under metal-free conditions, whereas the use of CuI (10 mol%) is able to redirect the cyclization to yield isoquinolinediones bearing an α-cyano quaternary carbon center. The cyclization features controllable divergent synthesis and a broad substrate scope as well as highly practical reaction conditions, thereby making this strategy a highly attractive means to fluorinate or cyanate isoquinolinediones.
authors.affiliation: College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China. stang@jsu.edu.cn.
authors.forename: You-Lin
authors.initials: YL
authors.lastname: Deng
authors.affiliation: College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China. stang@jsu.edu.cn.
authors.forename: Shi
authors.initials: S
authors.lastname: Tang
authors.affiliation: College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China. stang@jsu.edu.cn.
authors.forename: Guo-Liang
authors.initials: GL
authors.lastname: Ding
authors.affiliation: College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China. stang@jsu.edu.cn.
authors.forename: Ming-Wei
authors.initials: MW
authors.lastname: Wang
authors.affiliation: College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China. stang@jsu.edu.cn.
authors.forename: Jie
authors.initials: J
authors.lastname: Li
authors.affiliation: College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China. stang@jsu.edu.cn.
authors.forename: Zeng-Zeng
authors.initials: ZZ
authors.lastname: Li
authors.affiliation: College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China. stang@jsu.edu.cn.
authors.forename: Li
authors.initials: L
authors.lastname: Yuan
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Rui-Long
authors.initials: RL
authors.lastname: Sheng