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将伯磺酰胺无金属引入富电子芳烃。

Metal-free introduction of primary sulfonamide into electron-rich aromatics.

作者信息

Wang Ming-Ming, Johnsson Kai

机构信息

Department of Chemical Biology, Max Planck Institute for Medical Research Jahnstrasse 29 69120 Heidelberg Germany

Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL) 1015 Lausanne Switzerland.

出版信息

Chem Sci. 2024 Jul 5;15(31):12310-12315. doi: 10.1039/d4sc03075c. eCollection 2024 Aug 7.

Abstract

We report herein a direct and practical synthesis of arylsulfonamides from electron-rich aromatic compounds by using generated -sulfonylamine as the active electrophile. Substrates include derivatives of aniline, indole, pyrrole, furan, styrene and so on. The reaction proceeds under mild conditions and tolerates many sensitive functional groups such as alkyne, acetate, the trifluoromethoxy group or acetoxymethyl ester. Applications of this method for the construction of metal ion sensors and fluorogenic dye have been demonstrated, thus highlighting the potential of this method for probe development.

摘要

我们在此报告一种直接且实用的方法,即利用生成的磺酰胺作为活性亲电试剂,从富电子芳香化合物合成芳基磺酰胺。底物包括苯胺、吲哚、吡咯、呋喃、苯乙烯等的衍生物。该反应在温和条件下进行,并且能耐受许多敏感官能团,如炔基、乙酸酯基、三氟甲氧基或乙酰氧基甲酯。已证明该方法在构建金属离子传感器和荧光染料方面的应用,从而突出了该方法在探针开发方面的潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7073/11304520/4bc543cea138/d4sc03075c-s1.jpg

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