Thermal CO Release Reactivity of a π-Extended Flavonol Anion
The π-extended flavonol Flav-1 (<b>1</b>) undergoes reaction with KOH or KO<sub>2</sub> to form <b>1</b><sup><b>-</b></sup>, which reacts with O<sub>2</sub> at ambient temperature, resulting in CO release and depside formation. Mechanistic and DFT studies support a reaction pathway involving reaction of <b>1</b><sup><b>-</b></sup> with O<sub>2</sub> on the triplet energy surface in the rate-determining step. Formation of a cyclic peroxide leads to CO extrusion. These studies indicate that if formed in biological environments, <b>1</b><sup><b>-</b></sup> will release CO in the absence of light illumination.
Authors
- Tomasz Borowski (ORCID: https://orcid.org/0000-0002-3450-3576)
- Stephen N. Anderson (ORCID: https://orcid.org/0000-0002-7773-4761)
- Lisa M. Berreau (ORCID: https://orcid.org/0000-0001-9599-5239)
- C. Taylor Dederich (ORCID: https://orcid.org/0000-0002-8245-7914)
Institutions
- Utah State University (US)
- Jerzy Haber Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences (PL)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-21
- DOI
- https://doi.org/10.1021/acs.orglett.4c03651
- Citations
- 1
- Primary Topic
- Heme Oxygenase-1 and Carbon Monoxide
- Type
- article
- Field-Weighted Citation Impact
- 0.23
Funders
- Infrastruktura PL-Grid
- National Institutes of Health
- Academic Computer Centre Cyfronet, AGH University of Science and Technology
- National Institute of General Medical Sciences