Visible‐Light‐Promoted, (Photo)catalyst‐Free Synthesis of 3‐Sulfonyl‐Azaspiro[4.5]trienones via Arylazo Sulfones
Here, 3‐sulfonyl‐azaspiro[4.5]trienones are now accessible via a versatile visible‐light‐driven dearomative strategy under metal‐ and (photo)catalyst‐free conditions, starting from differently substituted N ‐aryl propiolamides and arylazo sulfones. The protocol employs ethyl acetate as a benign solvent and tert‐butyl hydroperoxide as the oxidant. The reaction proceeds through direct photoexcitation of the arylazo sulfone, which acts simultaneously as a light absorber and a sulfonyl‐radical source, enabling ipso‐spirocyclization of aromatic amides. This transformation combines a broad substrate scope with mild conditions and operational simplicity, providing a valuable synthetic entry to sulfur‐containing spiroheterocycles of pharmacological interest.
Authors
- Luc Neuville (ORCID: https://orcid.org/0000-0002-4648-2469)
- Maurizio Fagnoni (ORCID: https://orcid.org/0000-0003-0247-7585)
- Stefano Protti (ORCID: https://orcid.org/0000-0002-5313-5692)
- Géraldine Masson (ORCID: https://orcid.org/0000-0003-2333-7047)
- Luca Nicchio (ORCID: https://orcid.org/0000-0002-8467-2589)
- Giulia Pompilio
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut de Chimie des Substances Naturelles (FR)
- University of Pavia (IT)
- Joint Research Center (ES)
Publication Details
- Journal
- European Journal of Organic Chemistry
- Published
- 2026-04-17
- DOI
- https://doi.org/10.1002/ejoc.70410
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00