A variety of arenes and heteroarenes are brominated in good to excellent yields using N -bromosuccinimide (NBS) under mild and practical conditions. According to mechanistic investigations described within, the reaction is speculated to proceed via activation of NBS through a visible-light photoredox pathway utilizing erythrosine B as a photocatalyst. A photo-oxidative approach effectively amplifies the positive polarization on the bromine atom of the NBS reagent. This increase in the electrophilic nature of NBS results in drastically reduced reaction times and diversion from competing light-promoted reactive pathways.

A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhI[double bond, length as m-dash]NZ) and I has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.

The regioselective incorporation of a sulfonamide unit to a broad range of heteroarene scaffolds has been developed. Synthesized N-benzyl sulfonamides have been screened against a variety of cancer cell lines for cytotoxicity effects.