Synthesis of Acyclic Quaternary α-CF <sub>3</sub> -β-Oxo Carbonyls via Nucleophilic Substitution Induced by Single-Electron Transfer
The development of efficient methods for the formation of quaternary centers in organic compounds has been a constant challenge in synthetic chemistry. Quaternary β-oxo esters are fundamental structures in the synthesis of natural products, pharmaceutical compounds, and other bioactive molecules. In this work, a direct and versatile approach to quaternary noncyclic β-oxo esters is reported using trifluoromethyl thianthrenium salt as highly reactive and selective reagent under mild conditions. Mechanistic investigations supported the operation via single-electron transfer-induced nucleophilic substitution.
Authors
- Albert Granados (ORCID: https://orcid.org/0000-0002-5362-5966)
- Carolina Gimbert‐Suriñach (ORCID: https://orcid.org/0000-0002-4412-7607)
- Xiangyu Tan
- Adelina Vallribera (ORCID: https://orcid.org/0000-0002-6452-4589)
- Pau Sarró (ORCID: https://orcid.org/0000-0002-0957-2481)
- Elı́es Molins (ORCID: https://orcid.org/0000-0003-1012-0551)
- Roser Pleixats (ORCID: https://orcid.org/0000-0003-2544-732X)
Institutions
- Universitat Autònoma de Barcelona (ES)
- Institut de Ciència de Materials de Barcelona (ES)
- ORFEO-CINQA Research Network (ES)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-11-06
- DOI
- https://doi.org/10.1021/acs.joc.5c01559
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79