Synthesis of substituted 2H-Chromenes via Pd-catalyzed C-H activation and thermal cyclization

Abstract

A proficient approach has been developed for the synthesis of substituted 2H-chromenes from C1-substituted glucal. The key step of our synthetic methodology was C-H activation in propylene carbonate solvent followed by 6π-electrocyclization aromatization in ethylene glycol as greener substitutes to toxic aprotic solvents, to obtain 2H-chromenes in a stepwise manner. The application of the developed methodology was further explored with the synthesis of a small library of substituted 2H-chromenes in good yields.

Keywords: 2H-chromenes; 6π-electrocyclization aromatization reaction; Cross dehydrogenative coupling (CDC); C–H activation.