Electrochemical oxidative CF <sub>3</sub> radical-induced lactonization and etherification of terminal and internal alkenes
Introducing trifluoromethyl (CF<sub>3</sub>) groups enhances drug candidates' properties, improving metabolic stability and bioavailability. This study reports the electrochemical oxidation of Langlois' reagent for CF<sub>3</sub> radical-promoted cyclization, synthesizing functionalized lactones and cyclic ethers from terminal and internal alkenes with good to high yields. Mechanistic insights were supported by cyclic voltammetry, radical scavenger experiments, and DFT calculations. The protocol's efficiency highlights its potential in medicinal chemistry for developing pharmacologically valuable compounds avoiding the use of rare metal electrodes.
Authors
- Tommaso Fantoni (ORCID: https://orcid.org/0000-0002-9052-3432)
- Lucia Ferrazzano (ORCID: https://orcid.org/0000-0002-7083-2211)
- Walter Cabri (ORCID: https://orcid.org/0000-0001-7865-0474)
- Maria Lattanzi (ORCID: https://orcid.org/0000-0002-3457-426X)
- Alessandra Tolomelli (ORCID: https://orcid.org/0000-0003-4202-1136)
- Giuseppe Autuori
- Riccardo Grigolato
Institutions
- University of Bologna (IT)
Publication Details
- Journal
- RSC Advances
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ra01852h
- Citations
- 3
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 2.37
Funders
- Università di Bologna