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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 diamine 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 provides 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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Article information


Submitted
22 Jan 2020
Accepted
12 Feb 2020
First published
12 Feb 2020

Chem. Commun., 2020, Accepted Manuscript
Article type
Communication

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

L. Zhu, L. Tian, B. Cai, G. Liu, H. Zhang and Y. Wang, Chem. Commun., 2020, Accepted Manuscript , DOI: 10.1039/D0CC00601G

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