Transition-Metal Free Photocatalytic Synthesis of Acylsulfonamides

We have developed a transition-metal-free photocatalytic S-N coupling reaction utilizing sodium organosulfinate and hydroxamic acid to synthesize acylsulfonamides. Employing 2,3,5,6-tetra(9H-carbazol-9-yl)benzonitrile (4CzBN) as a photocatalyst, this method enables the preparation of a wide range of acylsulfonamides from arylhydroxamic acids or <i>N</i>-hydroxycarbamates. Mechanistic studies indicate that the generation of singlet oxygen (<sup>1</sup>O<sub>2</sub>) via the Energy Transfer Process (EnT) is crucial for facilitating the reaction. This approach offers a sustainable and efficient pathway for acylsulfonamide synthesis under mild conditions.

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Publication Details

Journal
Organic Letters
Published
2025-04-30
DOI
https://doi.org/10.1021/acs.orglett.5c01129
Citations
5
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
4.68

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article

Transition-Metal Free Photocatalytic Synthesis of Acylsulfonamides

Cong Ma, Long Yin Lam
5 citations
Organic Letters
Sulfur-Based Synthesis Techniques
4.68
article

Transition-Metal Free Photocatalytic Synthesis of Acylsulfonamides

Cong Ma, Long Yin Lam
article en
5 citations

Abstract

We have developed a transition-metal-free photocatalytic S-N coupling reaction utilizing sodium organosulfinate and hydroxamic acid to synthesize acylsulfonamides. Employing 2,3,5,6-tetra(9H-carbazol-9-yl)benzonitrile (4CzBN) as a photocatalyst, this method enables the preparation of a wide range of acylsulfonamides from arylhydroxamic acids or <i>N</i>-hydroxycarbamates. Mechanistic studies indicate that the generation of singlet oxygen (<sup>1</sup>O<sub>2</sub>) via the Energy Transfer Process (EnT) is crucial for facilitating the reaction. This approach offers a sustainable and efficient pathway for acylsulfonamide synthesis under mild conditions.

Organic LettersVol. 27(18)
Hong Kong Polytechnic University (HK)
Research Grants Council, University Grants Committee, Hong Kong Polytechnic University
Openalex Percentile: Top 6%
Sulfur-Based Synthesis Techniques
4.68
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Transition-Metal Free Photocatalytic Synthesis of Acylsulfonamides — Cong Ma, Long Yin Lam · Organic Letters (2025) | TGRS Research Map | TGRS