Sustainable Photocatalytic Synthesis of Glitazones via Riboflavin Tetraacetate
A more sustainable and versatile method to access antidiabetic glitazones is demanded. Herein, we report the unprecedented photocatalytic coupling of <i>N</i>-protected methylene thiazolidinediones with radical precursors (organoborates or carboxylic acids) under riboflavin tetraacetate catalysis. The methodology accepts various functional groups and affords (Het)Ar-(CH<sub>2</sub>)<sub>n</sub>-thiazolidinediones by transition-metal-free organic photoredox catalysis under mild conditions. The applicability of the developed protocol is showcased by the three-step preparation of the antidiabetic pioglitazone drug.
Authors
- Tracey Pirali (ORCID: https://orcid.org/0000-0003-3936-4787)
- Gianluca Papeo (ORCID: https://orcid.org/0000-0002-4773-4437)
- Rita Maria Concetta Di Martino (ORCID: https://orcid.org/0000-0003-2287-3331)
- Marina Caldarelli (ORCID: https://orcid.org/0000-0002-2492-8327)
- Sarah Jane Rezzi (ORCID: https://orcid.org/0009-0004-9471-0536)
- Marco Koten
Institutions
- Università degli Studi del Piemonte Orientale “Amedeo Avogadro” (IT)
- Nerviano Medical Sciences (IT)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-07-05
- DOI
- https://doi.org/10.1021/acs.joc.5c01306
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Associazione Italiana per la Ricerca sul Cancro
- Ministero dell'Università e della Ricerca