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Updated: Jun 17, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Metal-free introduction of primary sulfonamide into electron-rich aromatics
Ming-Ming Wang1, Kai Johnsson1,2
1Department of Chemical Biology, Max Planck Institute for Medical Research Jahnstrasse 29 69120 Heidelberg Germany mingming.wang@mr.mpg.de johnsson@mr.mpg.de.
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, 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.
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