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

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journal contribution
posted on 11.05.2016 by Walter D. Guerra, Roberto A. Rossi, Adriana B. Pierini, Silvia M. Barolo
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 = 395 nm) 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.