文献类型：期刊文献

英文题名：Aminochlorination of Alkenes with CFBSA

作者：Pu, Xiao-Qiu[1,2];Zhao, Hai-Yong[1,2];Lu, Ze-Hai[1,2];He, Xiao-Peng[1,2];Yang, Xian-Jin[1,2,3]

机构：[1]East China Univ Sci & Technol, Key Lab Adv Mat, 130 Meilong Rd, Shanghai, Peoples R China;[2]East China Univ Sci & Technol, Inst Fine Chem, 130 Meilong Rd, Shanghai, Peoples R China;[3]Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

年份：2016

卷号：2016

期号：26

起止页码：4526

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000383625600011)，CCR-EXPANDED(收录号:WOS:000383625600011)】；

基金：We are grateful to the National Natural Science Foundation of China (NSFC) (grant number 21372077) for financial support and Dr. Xiao-Peng He for his revision for the manuscript.

语种：英文

外文关键词：Alkenes; Aminochlorination; Sulfonamides; Chlorine

摘要：A novel catalyst-free aminochlorination of alkenes was developed by the direct addition of alkenes to N-chloro-N-fluorobenzenesulfonamide (CFBSA). The reaction produces 2-chloro-3-fluoramino and 3-chloro-2-fluoroamino adducts in 1,2-dichloroethane under reflux and dichloromethane at room temperature, respectively, in a regioselective manner. The electronic and steric effects of the fluorine atom of CFBSA have proven to be crucial for the reactivity and regioselectivity. A variety of transformations have been achieved to form 2-chloroenamines, chloroamines, aziridines and N-phenylbenzenesulfonamides under different conditions. Notably, the N-F bond in the adducts formed could be a useful handle for further transformations to useful compounds in organic synthesis.