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.

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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

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article

Generation of Sulfamoyl Radicals via Visible‐Light Mediated Fixation of Sulfur Dioxide for the Synthesis of Sulfonamides

Katja Heinze, Thais R. Arroio, Giuliano C. Clososki, Georg Manolikakes et al.
2 citations
Advanced Synthesis & Catalysis
Sulfur-Based Synthesis Techniques
0.50
article

Generation of Sulfamoyl Radicals via Visible‐Light Mediated Fixation of Sulfur Dioxide for the Synthesis of Sulfonamides

Katja Heinze, Thais R. Arroio, Giuliano C. Clososki, Georg Manolikakes, Jan Philipp Nau, Christoph Förster, Kamil Hofman, Jonathan Becker, Stephanie L. Faber
article en
2 citations

Abstract

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.

Advanced Synthesis & CatalysisVol. 367(1)
Universidade de Ribeirão Preto (BR), University of Kaiserslautern (DE), Universidade de São Paulo (BR), Johannes Gutenberg University Mainz (DE)
Fundação de Amparo à Pesquisa do Estado de São Paulo, Johannes Gutenberg-Universität Mainz
Openalex Percentile: Top 38%
Sulfur-Based Synthesis Techniques
0.50
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Generation of Sulfamoyl Radicals via Visible‐Light Mediated Fixation of Sulfur Dioxide for the Synthesis of Sulfonamides — Katja Heinze, Thais R. Arroio, et al. · Advanced Synthesis & Catalysis (2024) | TGRS Research Map | TGRS