Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 19, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200123
Keywords
Electrochemistry; Mechanistic investigations; Method development; Nucleophilic substitutions; Trifluoromethylselenolation
Categories
Funding
- French National Research Agency [ANR 18-CE07-0039-01]
- CNRS
- Universite Claude Bernard Lyon 1
- French Ministry of Research
- French Fluorine Network (GIS-FLUOR)
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A practical electrochemical method is reported in this study for the generation of CF3Se- anion from a stable reagent (TsSeCF3), enabling metal-free trifluoromethylselenolation of activated alkyl halides. Trifluoromethylselenolated compounds were obtained in moderate to excellent yields under optimized reaction conditions. Finally, cyclic voltammetric and F-19 NMR studies were conducted to gain insight into the reaction mechanism.
A practical electrochemical method for the generation of CF3Se- anion from a shelf-stable reagent (TsSeCF3) is reported allowing the metal-free trifluoromethylselenolation of activated alkyl halides. Trifluoromethylselenolated compounds have been obtained in modest to excellent yields under the optimized reaction conditions. Finally, cyclic voltammetric and F-19 NMR studies are presented and allowed to gain insight into the reaction mechanism.
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