The anodic oxidation of 1-butyl-3-methylimidazolium tetrafluoroborate (BMIm-BF4) efficiently generates BF3 from BF4-. This Lewis acid, strongly bound to the ionic liquids, can be efficiently used in classical BF3-catalyzed reactions. We demonstrated the BF3/BMIm-BF4 reactivity in four reactions, namely, a domino Friedel-Crafts/lactonization of phenols, the Povarov reaction, the Friedel-Crafts benzylation of anisole, and the multicomponent synthesis of tetrahydro-11H-benzo[a]xanthen-11-ones. In comparison with literature data using BF3-Et2O in organic solvents, in all the presented cases, analogous or improved results were obtained. Moreover, the noteworthy advantages of the developed method are the in situ generation of BF3 (no storing necessity) in the required amount, using only the electron as redox reagent, and the recycling of BMIm-BF4 for multiple subsequent runs.

In situ anodically oxidized BMIm-BF4: a safe and recyclable BF3 source / Bortolami, Martina; Mattiello, Leonardo; Scarano, Vincenzo; Vetica, Fabrizio; Feroci, Marta. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 86:22(2021), pp. 16151-16157. [10.1021/acs.joc.1c00932]

In situ anodically oxidized BMIm-BF4: a safe and recyclable BF3 source

Bortolami, Martina
Primo
;
Mattiello, Leonardo;Scarano, Vincenzo;Vetica, Fabrizio
Penultimo
;
Feroci, Marta
Ultimo
2021

Abstract

The anodic oxidation of 1-butyl-3-methylimidazolium tetrafluoroborate (BMIm-BF4) efficiently generates BF3 from BF4-. This Lewis acid, strongly bound to the ionic liquids, can be efficiently used in classical BF3-catalyzed reactions. We demonstrated the BF3/BMIm-BF4 reactivity in four reactions, namely, a domino Friedel-Crafts/lactonization of phenols, the Povarov reaction, the Friedel-Crafts benzylation of anisole, and the multicomponent synthesis of tetrahydro-11H-benzo[a]xanthen-11-ones. In comparison with literature data using BF3-Et2O in organic solvents, in all the presented cases, analogous or improved results were obtained. Moreover, the noteworthy advantages of the developed method are the in situ generation of BF3 (no storing necessity) in the required amount, using only the electron as redox reagent, and the recycling of BMIm-BF4 for multiple subsequent runs.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11573/1559777
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