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Aminochlorination of Alkenes with CFBSA
Author(s) -
Pu XiaoQiu,
Zhao HaiYong,
Lu ZeHai,
He XiaoPeng,
Yang XianJin
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600709
Subject(s) - regioselectivity , chemistry , steric effects , dichloromethane , reactivity (psychology) , adduct , dichloroethane , catalysis , medicinal chemistry , fluorine , halogenation , electronic effect , organic chemistry , medicine , alternative medicine , pathology , solvent
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.