Photocatalytic Three-Component Radical Sulfonarylation of Alkenes: Preparation of γ-Keto-Sulfone-Substituted Oxindoles

A photocatalytic radical sulfonarylation of <i>N</i>-arylacrylamides via a three-component cascade cyclopropyl alcohol ring opening/sulfur dioxide insertion/sulfonyl radical addition/cyclization sequence has been developed. This method employs cyclopropyl alcohols as the precursors of β-carbonyl alkyl radicals and Na<sub>2</sub>S<sub>2</sub>O<sub>5</sub> as a cheap source of sulfur dioxide. By using this cascade procedure, a wide variety of γ-keto-sulfone-substituted oxindoles were facilely synthesized.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-17
DOI
https://doi.org/10.1021/acs.joc.4c03174
Citations
6
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
5.62

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article

Photocatalytic Three-Component Radical Sulfonarylation of Alkenes: Preparation of γ-Keto-Sulfone-Substituted Oxindoles

Yunhong Jia, Yunhe Lv, Zheng Yang, Shu-Man Wang et al.
6 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
5.62
article

Photocatalytic Three-Component Radical Sulfonarylation of Alkenes: Preparation of γ-Keto-Sulfone-Substituted Oxindoles

Yunhong Jia, Yunhe Lv, Zheng Yang, Shu-Man Wang, Yixin Zhu, Fei Chen, Yinan Zhang, Yu-Xin Lai, Shuliao Tian, J. Li, Jun-Ya Guo
article en
6 citations

Abstract

A photocatalytic radical sulfonarylation of <i>N</i>-arylacrylamides via a three-component cascade cyclopropyl alcohol ring opening/sulfur dioxide insertion/sulfonyl radical addition/cyclization sequence has been developed. This method employs cyclopropyl alcohols as the precursors of β-carbonyl alkyl radicals and Na<sub>2</sub>S<sub>2</sub>O<sub>5</sub> as a cheap source of sulfur dioxide. By using this cascade procedure, a wide variety of γ-keto-sulfone-substituted oxindoles were facilely synthesized.

The Journal of Organic ChemistryVol. 90(12)
Shanghai Normal University (CN), Institute of Molecular Functional Materials (CN), Anyang Normal University (CN)
National Natural Science Foundation of China, Foundation of Henan Educational Committee, Natural Science Foundation of Henan Province, Anyang Normal University
Clean water and sanitation
Openalex Percentile: Top 5%
Sulfur-Based Synthesis Techniques
5.62
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