Tunable selective electrochemical selenization of tetrahydroquinolines with diselenides

Abstract

A simple and environmentally friendly electrochemical synthesis method is presented for the selenylation of tetrahydroquinolines with diselenides. By adjusting the reaction conditions, different products can be synthesized. Using NaI as the electrolyte and 2,2,6,6-tetramethylpiperidinooxy (TEMPO) as a redox mediator, C-3 selenylated quinolines were successfully synthesized, achieving the challenging C-3 substitution of quinolines. In the absence of TEMPO, C-6 selenylated tetrahydroquinolines were obtained. This green method offers excellent selectivity and a broad substrate scope, with reaction conditions that can be easily tuned to achieve different outcomes.