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

Author(s)

Arroio, Thais Rodrigues ; Nau, Jan Philipp ; Hofman, Kamil ; Foerster, Christoph ; Faber, Stephanie L. ; Becker, Sabine ; Heinze, Katja ; Clososki, Giuliano Cesar ; Manolikakes, Georg

• Document type: Journal article
• Source: ADVANCED SYNTHESIS & CATALYSIS; v. 367, n. 1, p. 6-pg., 2024-11-20.

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 SO2 or the SO2 surrogate DABSO (1,4-diazabicyclo[2.2.2]octane & sdot;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. (AU)

• FAPESP's process: 20/13962-9 - Synthetic studies aiming at the preparation of new pyridoindois of medicinal interest
• Grantee: Thais Rodrigues Arroio
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 22/08837-6 - Synthesis of (Hetero)Arylsulfonamides via photocatalytic C-H-sulfamoylation using sulfamoyl radicals
• Grantee: Thais Rodrigues Arroio
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate