Deep eutectic solvent-catalyzed Meyer–Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions
Nicolás Ríos‐Lombardía, Luciana Cicco, Kota Yamamoto, José A. Hernández-Fernández, Francisco Morís, Vito Capriati, Joaquín García‐Álvarez, Javier González‐Sabín
Abstract
The Meyer-Schuster rearrangement of propargylic alcohols into α,β-unsaturated carbonyl compounds has been revisited by setting up an atom-economic process catalyzed by a deep eutectic solvent FeCl3·6H2O/glycerol. Isomerizations take place smoothly, at room temperature, under air and with short reaction times. The unique solubilizing properties of the eutectic mixture enabled the use of a substrate concentration up to 1.0 M with the medium being recycled up to ten runs without any loss of catalytic activity.
Topics & Concepts
Deep eutectic solventEutectic systemSolventCatalysisChemistryGlycerolMedicinal chemistryRearrangement reactionOrganic chemistryAlloyIonic liquids properties and applicationsCatalytic Alkyne ReactionsOxidative Organic Chemistry Reactions