A structurally simple and reactive chlorinating reagent, N‐chloro‐N‐methoxybenzenesulfonamide, was conveniently and economically prepared in high yield. 1,3‐Diketones, β‐keto esters, benzoyl trifluoroacetones, phenols, anisoles, heteroarenes, and aromatic amines were successfully chlorinated, and the products were obtained in good to high yields.
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.
A novel rearrangement
reaction based on the structure of N-fluoro-N-alkyl benzenesulfonamide was
developed. The reaction proceeded readily at 50 °C in formic
acid and generated a variety of benzenesulfonamides and aldehydes
or ketones simultaneously. The reaction mechanism is believed to be
a concerted mechanism that consist of 1,2-aryl migration with the
departure of fluorine anion via an SN2 mechanism. This
rearrangement reaction features an interesting reaction mechanism,
mild reaction conditions, simple operations, and a broad substrate
scope.
A novel method for the synthesis of 2‐chloro enesulfonamides via the one‐pot addition‐elimination of N‐chloro‐N‐fluorobenzenesulfonamides (CFBSA) to styrenes in the presence of Et3N is described. A total of 20 examples are presented to illustrate this concept including various of styrenes.
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