Electrochemical oxidative CF₃ radical-induced lactonization and etherification of terminal and internal alkenes

Grigolato, Riccardo ; Fantoni, Tommaso ; Autuori, Giuseppe ; Lattanzi, Matteo ; Ferrazzano, Lucia ; Cabri, Walter ; Tolomelli, Alessandra (2025) Electrochemical oxidative CF₃ radical-induced lactonization and etherification of terminal and internal alkenes. University of Bologna. DOI 10.6092/unibo/amsacta/8336. [Dataset]
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Abstract

The dataset contains all the NMR spectra of the CF3 containing lactones and cyclic ethers synthetized with an electrochemical strategy. The protocol developed facilitates the synthesis of functionalized lactones and cyclic ethers from both terminal and internal alkenes exploiting the advantages of electrochemistry. Mechanistic insights, supported by cyclic voltammetry, radical trapping experiments, and DFT calculations, confirm the involvement of CF3 radicals. This metal-free protocol offers a sustainable and practical approach for accessing pharmacologically relevant scaffolds, underlining its potential for applications in medicinal chemistry.

Abstract
Document type
Dataset
Creators
CreatorsAffiliationORCID
Grigolato, RiccardoTolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry “Giacomo Ciamician”, University of Bologna, via Gobetti, 85-40129 Bologna, Italy
Fantoni, TommasoTolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry “Giacomo Ciamician”, University of Bologna, via Gobetti, 85-40129 Bologna, Italy0000-0002-9052-3432
Autuori, GiuseppeTolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry “Giacomo Ciamician”, University of Bologna, via Gobetti, 85-40129 Bologna, Italy
Lattanzi, MatteoTolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry “Giacomo Ciamician”, University of Bologna, via Gobetti, 85-40129 Bologna, Italy
Ferrazzano, LuciaTolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry “Giacomo Ciamician”, University of Bologna, via Gobetti, 85-40129 Bologna, Italy0000-0002-7083-2211
Cabri, WalterTolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry “Giacomo Ciamician”, University of Bologna, via Gobetti, 85-40129 Bologna, Italy0000-0001-7865-0474
Tolomelli, AlessandraTolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry “Giacomo Ciamician”, University of Bologna, via Gobetti, 85-40129 Bologna, Italy0000-0003-4202-1136
Keywords
Lactones, Cyclic ethers, Langlois, CF3, Electrochemistry
Subjects
DOI
Contributors
Name
Affiliation
ORCID
Type
Fantoni, Tommaso
Tolomelli-Cabri Lab, Center for Chemical Catalysis, Department of Chemistry “Giacomo Ciamician”, University of Bologna, via Gobetti, 85-40129 Bologna, Italy
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Deposit date
07 May 2025 09:32
Last modified
07 May 2025 09:46
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