Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air

Jian Ji; Cong Guan; Qinghua Wei; Xuwen Chen; Yun Zhao; Shunying Liu

doi:10.1021/acs.orglett.1c03743

Base-Induced Highly Regioselective Synthesis of N²-Substituted 1,2,3-Triazoles under Mild Conditions in Air

Org Lett. 2022 Jan 14;24(1):132-136. doi: 10.1021/acs.orglett.1c03743. Epub 2021 Dec 20.

Authors

Jian Ji¹, Cong Guan¹, Qinghua Wei¹, Xuwen Chen¹, Yun Zhao¹, Shunying Liu¹

Affiliation

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China.

PMID: 34928620
DOI: 10.1021/acs.orglett.1c03743

Abstract

We developed a highly regioselective base-induced synthesis of N²-substituted 1,2,3-triazoles from N-sulfonyl-1,2,3-triazoles and alkyl bromides/alkyl iodides at room temperature. We propose an S_N2-like mechanistic pathway to explain the high N²-regioselectivity. The protocol features a broad substrate scope and generates products in good to excellent yields (72-90%).