Diamine-mediated N2-selective β-selenoalkylation of triazoles with alkenes

Abstract

A N²-selective β-selenoalkylation of 1,2,3-triazoles with alkenes mediated by diamines has been developed. The reaction proceeds presumably via the interaction of diamines with both the triazole moiety and selenium/alkene complex to construct a U-shaped reaction intermediate. This activation mode will block the N¹ position on triazoles and thus favor the N²-selective selenoamination. This stereospecific anti-addition method enables an efficient N²-selective β-selenoalkylation of 1,2,3-triazoles under mild and open-air conditions and might find applications in the synthesis of biologically active molecules.