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无过渡金属光催化合成酰基磺酰胺

Transition-Metal Free Photocatalytic Synthesis of Acylsulfonamides.

作者信息

Lam Long Yin, Ma Cong

机构信息

State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, PolyU Marshall Research Centre for Medical Microbial Biotechnology, The Hong Kong Polytechnic University, Kowloon, Hong Kong SAR, China.

出版信息

Org Lett. 2025 May 9;27(18):4732-4736. doi: 10.1021/acs.orglett.5c01129. Epub 2025 Apr 30.

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 -hydroxycarbamates. Mechanistic studies indicate that the generation of singlet oxygen (O) 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.

摘要

我们开发了一种无过渡金属的光催化S-N偶联反应,利用有机亚磺酸钠和异羟肟酸合成酰基磺酰胺。以2,3,5,6-四(9H-咔唑-9-基)苯甲腈(4CzBN)作为光催化剂,该方法能够从芳基异羟肟酸或羟基氨基甲酸酯制备多种酰基磺酰胺。机理研究表明,通过能量转移过程(EnT)产生单线态氧(O)对于促进反应至关重要。该方法为在温和条件下合成酰基磺酰胺提供了一条可持续且高效的途径。

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