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.

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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

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article

Electrochemical oxidative CF 3 radical-induced lactonization and etherification of terminal and internal alkenes

Tommaso Fantoni, Lucia Ferrazzano, Walter Cabri, Maria Lattanzi et al.
3 citations
RSC Advances
Fluorine in Organic Chemistry
2.37
article

Electrochemical oxidative CF 3 radical-induced lactonization and etherification of terminal and internal alkenes

Tommaso Fantoni, Lucia Ferrazzano, Walter Cabri, Maria Lattanzi, Alessandra Tolomelli, Giuseppe Autuori, Riccardo Grigolato
article en
3 citations

Abstract

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.

RSC AdvancesVol. 15(19)
University of Bologna (IT)
Università di Bologna
Clean water and sanitation
Openalex Percentile: Top 12%
Fluorine in Organic Chemistry
2.37
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