Greener Synthesis of 4-Selanyl-Isocoumarins Mediated by TCCA: Electrochemical Insights and DNA Interaction Studies

We present a straightforward and sustainable approach for the synthesis of 4-selanyl-isocoumarins from 2-(alkynyl)-aryl or -heteroaryl and diorganoyl diselenides. This transformation employs trichloroisocyanuric acid (TCCA) as a low-cost, metal-free oxidant under ambient conditions, delivering the desired products in yields of up to 98%. Mechanistic investigations support an electrophilic activation of the alkyne followed by a 6-endo-dig cyclization. Electrochemical and DFT analyses confirm the redox activity and structural stability of the resulting compounds. Additionally, DNA binding studies, combining UV-vis spectroscopy and molecular docking, reveal dual interaction modes (intercalation and groove binding), underscoring their potential in DNA-targeted drug design.