Mild synthesis of benzo[d]thiazoles and chalcogenol esters through reduction of disulfides and diselenides promoted by enamine-based organic electron donors

Abstract

The reduction of disulfide bridges (S–S) has attracted growing attention, as they serve as stable and non-odoriferous thiol precursors. To prove the ability of enamine-based organic electron donors (OEDs) in original S–S bond cleavage reactivities, we undertook here the synthesis of benzothiazoles through OED-promoted reduction of disulfide bridges. The metal-free and mild conditions enabled the synthesis of benzothiazoles with a wide tolerance to different functional groups and good yields. Synthesis of thio- or seleno-benzoates from the reduction of disulfide or diselenide was also obtained.