文献类型：期刊文献

英文题名：Copper-Catalyzed Cascade Transformation of Homopropargyl Azides into Trifluoromethylated Nitriles via C-C Cleavage

作者：Chen, Shuang;Li, Deng-Yuan[1];Jiang, Liang-Liang;Liu, Kai;Liu, Pei-Nian[1]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, Meilong Rd 130, Shanghai 200237, Peoples R China; East China Univ Sci & Technol, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China

年份：2017

卷号：19

期号：8

起止页码：2014

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000400123600020)，CCR-EXPANDED(收录号:WOS:000400123600020)】；

基金：This research was supported by the National Natural Science Foundation of China (Project Nos. 21372072, 21602059, 21561162003, and 21672059), the Eastern Scholar Distinguished Professor Program, the Postdoctoral Fund in China Postdoctoral Science Foundation (2015M581542 and 2016T90341), and the Fundamental Research Funds for the Central Universities.

语种：英文

摘要：A cascade reaction of homopropargyl azides in the presence of a Cu catalyst was achieved, affording 3-(trifluoromethyl)but-3-enenitriles with good yields and excellent regioselectivity. This reaction appears to be the first direct conversion of homopropargyl azides into trifluoromethylated nitriles. Mechanistic studies indicate that the transformation proceeds by addition of a CF3 radical to the alkyne, C-C cleavage by 1,4-aryl radical migration, and nitrile formation. This protocol provides a novel strategy for transforming azides into nitriles via C-C cleavage derived from radical migration.