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Electrochemical oxidative CF3 radical-induced lactonization and etherification of terminal and internal alkenes
Riccardo Grigolato1, Tommaso Fantoni1, Giuseppe Autuori1
1Tolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry "Giacomo Ciamician", University of Bologna Via Gobetti 85-40129 Bologna Italy tommaso.fantoni3@unibo.it walter.cabri@unibo.it.
Abstract:
Introducing trifluoromethyl (CF3) groups enhances drug candidates' properties, improving metabolic stability and bioavailability. This study reports the electrochemical oxidation of Langlois' reagent for CF3 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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