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


School of Chemistry and Chemical Engineering, Zhoukou Normal University, Wenchang Road, Zhoukou, 466001, China. [Email]


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.

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