Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 12, Pages 4965-4973Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00330
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- Agencia Cordoba Ciencia
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET)
- Secretaria de Ciencia y Tecnologia, Universidad Nacional de Cordoba (SECyT)
- Agencia Nacional de Promocion Cientifica y Tecnica (ANPCyT)
- CONICET
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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 (lambda = 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 S(RN)1 process.
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