Issue 31, 2024

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

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.

Graphical abstract: Metal-free introduction of primary sulfonamide into electron-rich aromatics

Supplementary files

Article information

Article type
Edge Article
Submitted
10 maj 2024
Accepted
04 jul 2024
First published
05 jul 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 12310-12315

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

M. Wang and K. Johnsson, Chem. Sci., 2024, 15, 12310 DOI: 10.1039/D4SC03075C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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