Highly Regioselective Butylation of N-Sulfonyl-1,2,3-triazoles by the Formation of Quaternary Carbon-Centered C(sp3)─N Bonds

Jian Ji; Jinhua Liu; Yaqi Deng; Zongjing Hu; Shunying Liu

doi:10.1002/ajoc.202500353

Highly Regioselective Butylation of N-Sulfonyl-1,2,3-triazoles by the Formation of Quaternary Carbon-Centered C(sp³)─N Bonds

Jian Ji
, Jinhua Liu
, Yaqi Deng
, Zongjing Hu
, 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

Abstract

An efficient example of quaternary carbon-centered C(sp³)─N bond formation has been developed using N-sulfonyl-1,2,3-triazoles and tert-butyl hydroperoxide with a high regioselectivity in good yields (71%–83%) without any additional catalysts or additives. The unprecedented reaction was possibly promoted by a radical addition to triazoles followed by an aromatic desulfonation process.

Original language	English
Article number	e00353
Journal	Asian Journal of Organic Chemistry
Volume	14
Issue number	10
DOIs	https://doi.org/10.1002/ajoc.202500353
State	Published - Oct 2025

Keywords

C(sp)─N bond
Desulfonation
N-Sulfonyl-1,2,3-triazoles

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10.1002/ajoc.202500353

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title = "Highly Regioselective Butylation of N-Sulfonyl-1,2,3-triazoles by the Formation of Quaternary Carbon-Centered C(sp3)─N Bonds",

abstract = "An efficient example of quaternary carbon-centered C(sp3)─N bond formation has been developed using N-sulfonyl-1,2,3-triazoles and tert-butyl hydroperoxide with a high regioselectivity in good yields (71\%–83\%) without any additional catalysts or additives. The unprecedented reaction was possibly promoted by a radical addition to triazoles followed by an aromatic desulfonation process.",

keywords = "C(sp)─N bond, Desulfonation, N-Sulfonyl-1,2,3-triazoles",

author = "Jian Ji and Jinhua Liu and Yaqi Deng and Zongjing Hu and Shunying Liu",

note = "Publisher Copyright: {\textcopyright} 2025 Wiley-VCH GmbH.",

year = "2025",

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doi = "10.1002/ajoc.202500353",

language = "英语",

volume = "14",

journal = "Asian Journal of Organic Chemistry",

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T1 - Highly Regioselective Butylation of N-Sulfonyl-1,2,3-triazoles by the Formation of Quaternary Carbon-Centered C(sp3)─N Bonds

AU - Ji, Jian

AU - Liu, Jinhua

AU - Deng, Yaqi

AU - Hu, Zongjing

AU - Liu, Shunying

PY - 2025/10

Y1 - 2025/10

N2 - An efficient example of quaternary carbon-centered C(sp3)─N bond formation has been developed using N-sulfonyl-1,2,3-triazoles and tert-butyl hydroperoxide with a high regioselectivity in good yields (71%–83%) without any additional catalysts or additives. The unprecedented reaction was possibly promoted by a radical addition to triazoles followed by an aromatic desulfonation process.

AB - An efficient example of quaternary carbon-centered C(sp3)─N bond formation has been developed using N-sulfonyl-1,2,3-triazoles and tert-butyl hydroperoxide with a high regioselectivity in good yields (71%–83%) without any additional catalysts or additives. The unprecedented reaction was possibly promoted by a radical addition to triazoles followed by an aromatic desulfonation process.

KW - C(sp)─N bond

KW - Desulfonation

KW - N-Sulfonyl-1,2,3-triazoles

UR - https://www.scopus.com/pages/publications/105011938260

U2 - 10.1002/ajoc.202500353

DO - 10.1002/ajoc.202500353

M3 - 文章

AN - SCOPUS:105011938260

SN - 2193-5807

VL - 14

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 10

M1 - e00353

ER -

Highly Regioselective Butylation of N-Sulfonyl-1,2,3-triazoles by the Formation of Quaternary Carbon-Centered C(sp³)─N Bonds

Abstract

Keywords

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