Synthesis of Dibenzosultams by “Transition-Metal-Free” Photoinduced Intramolecular Arylation of N-Aryl-2-halobenzenesulfonamides

• DOI: 10.1021/acs.joc.6b00330
• Publication Date: 2016-05-11T17:56:27Z
• Authors: Walter D. Guerra; Roberto A. Rossi; Adriana B. Pierini; Silvia M. Barolo
• Keywords: Intramolecular reaction

A new and general synthetic route to prepare dibenzosultams is here reported. This approach involves the synthesis of N-aryl-2-halobenzenesulfonamides (3), followed by intramolecular C-C photoinduced arylation under soft conditions without use "Transition Metal". The photostimulated reactions exhibit very good tolerance different substituent groups with excellent isolated yields (42-98%) products. Moreover, it shown that LED (λ = 395 nm) an efficient light energy source initiate efficiently reactions. Theoretical inspection mechanism was made probe involvement radical-anion SRN1 process.