Catalyst-Free Radical Carbosulfonylation of Enamides with Indoles, Aryldiazonium Tetrafluoroborates, and DABCO·(SO<sub>2</sub>)<sub>2</sub>

Herein, we have developed a catalyst-free four-component carbosulfonylation of enamides involving indoles, DABCO·(SO<sub>2</sub>)<sub>2</sub>, and aryldiazonium tetrafluoroborates for the preparation of various β-amidosulfone products in moderate to excellent yields. This approach features mild reaction conditions, high step-efficiency, and broad substrate scope, which provides a green and efficient strategy for carbosulfonyl difunctionalization of enamides. Based on the results of mechanism studies, a radical tandem reaction process is proposed for the transformation.

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Publication Details

Journal
Organic Letters
Published
2024-09-23
DOI
https://doi.org/10.1021/acs.orglett.4c03009
Citations
8
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.00

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article

Catalyst-Free Radical Carbosulfonylation of Enamides with Indoles, Aryldiazonium Tetrafluoroborates, and DABCO·(SO2)2

Hao Cheng, Jie Wu, Changmei Zhang, Danqing Zheng et al.
8 citations
Organic Letters
Sulfur-Based Synthesis Techniques
2.00
article

Catalyst-Free Radical Carbosulfonylation of Enamides with Indoles, Aryldiazonium Tetrafluoroborates, and DABCO·(SO2)2

Hao Cheng, Jie Wu, Changmei Zhang, Danqing Zheng, Shaoyu Li, Yuanyuan An
article en
8 citations

Abstract

Herein, we have developed a catalyst-free four-component carbosulfonylation of enamides involving indoles, DABCO·(SO<sub>2</sub>)<sub>2</sub>, and aryldiazonium tetrafluoroborates for the preparation of various β-amidosulfone products in moderate to excellent yields. This approach features mild reaction conditions, high step-efficiency, and broad substrate scope, which provides a green and efficient strategy for carbosulfonyl difunctionalization of enamides. Based on the results of mechanism studies, a radical tandem reaction process is proposed for the transformation.

Organic LettersVol. 26(39)
Nanjing Tech University (CN), Chinese Academy of Sciences (CN), Shanghai Institute of Organic Chemistry (CN), Taizhou University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Jiangsu Province, China Academy of Space Technology
Openalex Percentile: Top 14%
Sulfur-Based Synthesis Techniques
2.00
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