The anodic oxidation of tetrafluoroborate anion yields the Lewis acid BF3. If this reaction is carried out in an imidazolium ionic liquid, a quite stable system containing BF3 is obtained, whose reactivity is similar to the one of BF3·Et2O, but less harmful. The two reagents' stabilities were compared by computational analysis, strongly suggesting a higher stability for BF3/BMIm-BF4 system. The effect of substituents on the imidazolium ring and of the electrochemical configuration on BF3 reactivity were studied in a model reaction, styrene oxide isomerization. The experimental conditions were defined for the selective formation of phenylacetaldehyde or of 2-benzyl-4-phenyl-1,3-dioxolane. Moreover, the formation of N-heterocyclic carbene-BF3 adduct was confirmed when carrying out the electrolysis in an undivided cell. Electrogenerated BF3/BMIm-BF4 system demonstrated to be a valid alternative to commercial BF3·Et2O.

Electrogenerated {BF}3 from tetrafluoroborate-based ionic liquids: theoretical and experimental studies towards selective styrene oxide isomerization / Bortolami, Martina; Magboo, Fernando Junior Piamonte; Petrucci, Rita; Vetica, Fabrizio; Zollo, Giuseppe; Feroci, Marta. - In: JOURNAL OF THE ELECTROCHEMICAL SOCIETY. - ISSN 0013-4651. - 168:11(2021). [10.1149/1945-7111/ac39e2]

Electrogenerated {BF}3 from tetrafluoroborate-based ionic liquids: theoretical and experimental studies towards selective styrene oxide isomerization

Martina Bortolami
Primo
;
Fernando Piamonte Magboo
Secondo
;
Rita Petrucci;Fabrizio Vetica;Giuseppe Zollo
Penultimo
;
Marta Feroci
Ultimo
2021

Abstract

The anodic oxidation of tetrafluoroborate anion yields the Lewis acid BF3. If this reaction is carried out in an imidazolium ionic liquid, a quite stable system containing BF3 is obtained, whose reactivity is similar to the one of BF3·Et2O, but less harmful. The two reagents' stabilities were compared by computational analysis, strongly suggesting a higher stability for BF3/BMIm-BF4 system. The effect of substituents on the imidazolium ring and of the electrochemical configuration on BF3 reactivity were studied in a model reaction, styrene oxide isomerization. The experimental conditions were defined for the selective formation of phenylacetaldehyde or of 2-benzyl-4-phenyl-1,3-dioxolane. Moreover, the formation of N-heterocyclic carbene-BF3 adduct was confirmed when carrying out the electrolysis in an undivided cell. Electrogenerated BF3/BMIm-BF4 system demonstrated to be a valid alternative to commercial BF3·Et2O.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11573/1585434
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