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

Jian Ji
, Cong Guan
, Qinghua Wei
, Xuwen Chen
, Yun Zhao
, Shunying Liu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

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%).

Original language	English
Pages (from-to)	132-136
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.1c03743
State	Published - 14 Jan 2022

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

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 SN2-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\%).",

author = "Jian Ji and Cong Guan and Qinghua Wei and Xuwen Chen and Yun Zhao and Shunying Liu",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society",

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T1 - Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air

AU - Ji, Jian

AU - Guan, Cong

AU - Wei, Qinghua

AU - Chen, Xuwen

AU - Zhao, Yun

AU - Liu, Shunying

PY - 2022/1/14

Y1 - 2022/1/14

N2 - 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 SN2-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%).

AB - 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 SN2-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%).

UR - https://www.scopus.com/pages/publications/85122020756

U2 - 10.1021/acs.orglett.1c03743

DO - 10.1021/acs.orglett.1c03743

M3 - 文章

C2 - 34928620

AN - SCOPUS:85122020756

SN - 1523-7060

VL - 24

SP - 132

EP - 136

JO - Organic Letters

JF - Organic Letters

IS - 1

ER -

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

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