Iron-Mediated Nitrate Reduction at Ambient Temperature for Deaminative Sulfonylation and Fluorination of Anilines
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 <i>in situ</i> 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.
Authors
- Tobias Ritter (ORCID: https://orcid.org/0000-0002-6957-450X)
- Ahmet Altun (ORCID: https://orcid.org/0000-0001-8818-9925)
- Moritz Krebs (ORCID: https://orcid.org/0000-0002-0908-4816)
- Davide Carboni (ORCID: https://orcid.org/0000-0003-2499-4567)
- Javier Mateos (ORCID: https://orcid.org/0000-0002-2358-9183)
- Markus Leutzsch (ORCID: https://orcid.org/0000-0001-8171-9399)
- Annika Höppner
- Felix Waldbach (ORCID: https://orcid.org/0009-0001-2030-0874)
- Deepak Behera (ORCID: https://orcid.org/0009-0007-9351-6282)
- Tim Schulte (ORCID: https://orcid.org/0009-0003-3976-1907)
Institutions
- Max-Planck-Institut für Kohlenforschung (DE)
- RWTH Aachen University (DE)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-05-09
- DOI
- https://doi.org/10.1021/jacs.4c17981
- Citations
- 7
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 6.55
Funders
- Deutsche Forschungsgemeinschaft
- Max-Planck-Gesellschaft