Intramolecular Arylation of 2‐Bromobenzenesulfonamides Using DMSO/HCOONa ⋅ 2H₂O System: An Access To Dibenzosultams

Abstract

Six-or seven-membered dibenzosultams were synthesized upon treatment of N-aryl-or N-benzyl-2halobenzenesulfonamides with HCOONa • 2H 2 O in DMSO without using additional measures and additives, such as light irradiation, electrochemical apparatus, transition metals, and oxidants. Further functionalization of the free NH group of the resultant dibenzosultams demonstrates the synthetic practicability of this method.

Reductive Hydrodehalogenation of Halogenated Carboxylic Acid Derivatives Using a DMSO/HCOONa·2H2O System

“…13 Additionally, an intramolecular arylation of N-aryl-or N-benzyl-2-halobenzenesulfonamides using a DMSO/HCOONa•2H 2 O system was also developed to afford six-or seven-membered dibenzosultams. 14 Herein, we report a novel reductive hydrodehalogenation of halogenated carboxylic acid derivatives by using a DMSO/HCOONa•2H 2 O system (Scheme 1). To the best of our knowledge, there have been very few reports with regard to the light-, electrolysis-, strong base-, and metal-free hydrodehalogenation of halo- genated carboxylic acid derivatives.…”

“…Indeed, we have already disclosed a catalyst- and additive-free chemoselective transfer hydrogenation of α-keto amides to α-hydroxy amides by using a DMSO/HCOONa·2H 2 O system . Additionally, an intramolecular arylation of N -aryl- or N -benzyl-2-halobenzenesulfonamides using a DMSO/HCOONa·2H 2 O system was also developed to afford six- or seven-membered dibenzosultams . Herein, we report a novel reductive hydrodehalogenation of halogenated carboxylic acid derivatives by using a DMSO/HCOONa·2H 2 O system (Scheme ).…”