Copper-Catalyzed Intermolecular 1,2-Carbotriazolization of Alkenes with N-Sulfonyl-1,2,3-Triazoles and Aldehydes

Jian Ji; Zongjing Hu; Cong Guan; Jinhua Liu; Yaqi Deng; Xuwen Chen; Shunying Liu

doi:10.1021/acssuschemeng.3c04487

Copper-Catalyzed Intermolecular 1,2-Carbotriazolization of Alkenes with N-Sulfonyl-1,2,3-Triazoles and Aldehydes

Jian Ji
, Zongjing Hu
, Cong Guan
, Jinhua Liu
, Yaqi Deng
, Xuwen Chen
, 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

11 Scopus citations

Abstract

The first efficient example of the 1,2-carbotriazolization of alkenes with N-sulfonyl-1,2,3-triazoles and aldehydes was developed as an appealing strategy for producing β-triazolized ketones via a copper-catalyzed radical relay process. The products were constructed in one pot with high regioselectivity and chemoselectivity as well as a wide range of substrate scopes, including aromatic and aliphatic aldehydes and alcohols. Preliminary mechanistic study indicates that the reaction proceeds via an S_N2-like tandem radical relay desulfonation process. The resulting β-triazolized ketone scaffold shows a good and selective inhibitory activity on osteosarcoma (OS) cell lines at 10 μM, which is promising for use as an efficient pharmacophore for drug discovery.

Original language	English
Pages (from-to)	16240-16248
Number of pages	9
Journal	ACS Sustainable Chemistry and Engineering
Volume	11
Issue number	45
DOIs	https://doi.org/10.1021/acssuschemeng.3c04487
State	Published - 13 Nov 2023

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Keywords

1,2,3-triazoles
1,2-carboamination
1,2-carbotriazolization
desulfonation
radical relay

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10.1021/acssuschemeng.3c04487

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title = "Copper-Catalyzed Intermolecular 1,2-Carbotriazolization of Alkenes with N-Sulfonyl-1,2,3-Triazoles and Aldehydes",

abstract = "The first efficient example of the 1,2-carbotriazolization of alkenes with N-sulfonyl-1,2,3-triazoles and aldehydes was developed as an appealing strategy for producing β-triazolized ketones via a copper-catalyzed radical relay process. The products were constructed in one pot with high regioselectivity and chemoselectivity as well as a wide range of substrate scopes, including aromatic and aliphatic aldehydes and alcohols. Preliminary mechanistic study indicates that the reaction proceeds via an SN2-like tandem radical relay desulfonation process. The resulting β-triazolized ketone scaffold shows a good and selective inhibitory activity on osteosarcoma (OS) cell lines at 10 μM, which is promising for use as an efficient pharmacophore for drug discovery.",

keywords = "1,2,3-triazoles, 1,2-carboamination, 1,2-carbotriazolization, desulfonation, radical relay",

author = "Jian Ji and Zongjing Hu and Cong Guan and Jinhua Liu and Yaqi Deng and Xuwen Chen and Shunying Liu",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society",

year = "2023",

month = nov,

day = "13",

doi = "10.1021/acssuschemeng.3c04487",

language = "英语",

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pages = "16240--16248",

journal = "ACS Sustainable Chemistry and Engineering",

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TY - JOUR

T1 - Copper-Catalyzed Intermolecular 1,2-Carbotriazolization of Alkenes with N-Sulfonyl-1,2,3-Triazoles and Aldehydes

AU - Ji, Jian

AU - Hu, Zongjing

AU - Guan, Cong

AU - Liu, Jinhua

AU - Deng, Yaqi

AU - Chen, Xuwen

AU - Liu, Shunying

PY - 2023/11/13

Y1 - 2023/11/13

N2 - The first efficient example of the 1,2-carbotriazolization of alkenes with N-sulfonyl-1,2,3-triazoles and aldehydes was developed as an appealing strategy for producing β-triazolized ketones via a copper-catalyzed radical relay process. The products were constructed in one pot with high regioselectivity and chemoselectivity as well as a wide range of substrate scopes, including aromatic and aliphatic aldehydes and alcohols. Preliminary mechanistic study indicates that the reaction proceeds via an SN2-like tandem radical relay desulfonation process. The resulting β-triazolized ketone scaffold shows a good and selective inhibitory activity on osteosarcoma (OS) cell lines at 10 μM, which is promising for use as an efficient pharmacophore for drug discovery.

AB - The first efficient example of the 1,2-carbotriazolization of alkenes with N-sulfonyl-1,2,3-triazoles and aldehydes was developed as an appealing strategy for producing β-triazolized ketones via a copper-catalyzed radical relay process. The products were constructed in one pot with high regioselectivity and chemoselectivity as well as a wide range of substrate scopes, including aromatic and aliphatic aldehydes and alcohols. Preliminary mechanistic study indicates that the reaction proceeds via an SN2-like tandem radical relay desulfonation process. The resulting β-triazolized ketone scaffold shows a good and selective inhibitory activity on osteosarcoma (OS) cell lines at 10 μM, which is promising for use as an efficient pharmacophore for drug discovery.

KW - 1,2,3-triazoles

KW - 1,2-carboamination

KW - 1,2-carbotriazolization

KW - desulfonation

KW - radical relay

UR - https://www.scopus.com/pages/publications/85178329218

U2 - 10.1021/acssuschemeng.3c04487

DO - 10.1021/acssuschemeng.3c04487

M3 - 文章

AN - SCOPUS:85178329218

SN - 2168-0485

VL - 11

SP - 16240

EP - 16248

JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

IS - 45

ER -

Copper-Catalyzed Intermolecular 1,2-Carbotriazolization of Alkenes with N-Sulfonyl-1,2,3-Triazoles and Aldehydes

Abstract

UN SDGs

Keywords

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