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

Wang, Ming-Ming; Johnsson, Kai

doi:10.1039/D4SC03075C

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

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Wang, Ming-Ming
Chemical Biology, Max Planck Institute for Medical Research, Max Planck Society;

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Johnsson, Kai
Chemical Biology, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Wang, M.-M., & Johnsson, K. (2024). Metal-free introduction of primary sulfonamide into electron-rich aromatics. Chemical Science, 15(31), 12310-12315. doi:10.1039/D4SC03075C.

Cite as: https://hdl.handle.net/21.11116/0000-000F-8658-7

Abstract

We report herein a direct and practical synthesis of arylsulfonamides from electron-rich aromatic compounds by using in-situ generated N-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, 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.