Synthesis of Dibenzosultams by ?Transition-Metal-Free? Photoinduced Intramolecular Arylation of N‑Aryl-2- halobenzenesulfonamides

WALTER D. GUERRA; SILVIA M. BAROLO; ADRIANA B. PIERINI; R. A. ROSSI,

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2016 vol. 81 p. 4965 - 4973

0022-3263

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 the use of ?Transition Metal?. The photostimulated reactions exhibit very good tolerance to different substituent groups with good to excellent isolated yields (42−98%) of products. Moreover, it is shown that LED (λ = 395nm) is an efficient light energy source to initiate efficiently the reactions. Theoretical inspection of the mechanism was made to probe the involvement of the radical-anion SRN1 process.