期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2016, 期 26, 页码 4526-4533出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201600709
关键词
Alkenes; Aminochlorination; Sulfonamides; Chlorine
资金
- National Natural Science Foundation of China (NSFC) [21372077]
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.
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