Iron-Mediated Nitrate Reduction at Ambient Temperature for Deaminative Sulfonylation and Fluorination of Anilines
Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Preparation of arylsulfonic acids and derivatives can be achieved under mild conditions from aryldiazonium salts, although conventional methods often require isolation or accumulation of these potentially hazardous intermediates. Herein, we present that iron nitrate reduction at 25 °C enables the in situ generation of diazonium salts, which allows direct deaminative chlorosulfonylation and fluorination from anilines via aryldiazonium salts as fleeting intermediates. Other sulfonic acid derivatives, such as sulfonamides, sulfonyl fluorides, and sulfonic acids, are readily accessible from this method.
DOI: 10.1021/jacs.4c17981
Authors: Tim Schulte, Deepak Behera, Davide Carboni, Annika Höppner, Felix Waldbach, Javier Mateos, Ahmet Altun, Markus Leutzsch, Moritz L. Krebs, Tobias Ritter
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Award: G230394868
OpenAlex ID: W4410243603