Synthesis of 2,5-disubstituted selenophenes via a copper-catalyzed regioselective [2+2+1] cyclization of terminal alkynes and selenium

Abstract

Herein, a straightforward method for the synthesis of 2,5-disubstituted selenophenes via [2+2+1] cyclization of easily accessible terminal alkynes and elemental selenium has been developed. This reaction features high atom- and step-economy, excellent regioselectivity, good functional group tolerance and the use of stable and non-toxic selenium as a selenium source. A series of control experiments suggests that the reaction might undergo Glaser coupling reaction of two molecules of alkynes, followed by insertion of H₂Se and subsequent cyclization. Moreover, the newly formed products can be further converted to diverse conjugated selenophene-based derivatives, demonstrating their potential applications in organic synthesis and materials science.