Generation of Sulfamoyl Radicals via Visible‐Light Mediated Fixation of Sulfur Dioxide for the Synthesis of Sulfonamides
Abstract Herein, we report a new approach for the light‐mediated generation of sulfamoyl radicals using sulfur dioxide as key building block and the direct application of these radicals in the synthesis of sulfonamides. In the presence of different photoredox catalysts, sulfamoyl radicals can be generated directly from SO 2 or the SO 2 surrogate DABSO (1,4‐diazabicyclo[2.2.2]octane⋅bis (sulfur dioxide) adduct) and N ‐aminopyridinium salts as nitrogen radical precursors. Trapping of the in situ generated sulfamoyl radicals with selected electron‐rich olefins affords different sulfonamides in up to 86% yield in a three‐component procedure. This transformation provides a complementary approach for the in situ generation of sulfamoyl radicals as synthetic intermediates for the assembly of the sulfonamide functionality, a privileged motif in active pharmaceutical ingredients.
Authors
- Katja Heinze (ORCID: https://orcid.org/0000-0003-1483-4156)
- Thais R. Arroio (ORCID: https://orcid.org/0000-0001-6998-0762)
- Giuliano C. Clososki (ORCID: https://orcid.org/0000-0001-7605-4150)
- Georg Manolikakes (ORCID: https://orcid.org/0000-0002-4013-5757)
- Jan Philipp Nau
- Christoph Förster (ORCID: https://orcid.org/0000-0003-4971-5368)
- Kamil Hofman
- Jonathan Becker (ORCID: https://orcid.org/0000-0001-8566-5690)
- Stephanie L. Faber
Institutions
- Universidade de Ribeirão Preto (BR)
- University of Kaiserslautern (DE)
- Universidade de São Paulo (BR)
- Johannes Gutenberg University Mainz (DE)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-10-18
- DOI
- https://doi.org/10.1002/adsc.202401065
- Citations
- 2
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Fundação de Amparo à Pesquisa do Estado de São Paulo
- Johannes Gutenberg-Universität Mainz