The Mechanochemical Beckmann Rearrangement: An Eco-efficient “Cut-and-Paste” Strategy to Design the “Good Old Amide Bond” - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue ACS Sustainable Chemistry & Engineering Année : 2021

The Mechanochemical Beckmann Rearrangement: An Eco-efficient “Cut-and-Paste” Strategy to Design the “Good Old Amide Bond”

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Discovered over a century ago, Beckmann rearrangement is still today fully compliant with all the green chemistry principles and consistent with the key aspects of sustainable development. Herein, we report on a sustainable mechanochemical procedure allowing the design of new amide frameworks via an eco-efficient "cut-and-paste" process of C-C and C-N bonds on the oxime backbone. We combined inexpensive and readily available reagents, such as p-tosyl imidazole (p-Ts-Im) and oxalic acid, to prepare smoothly and in good to high yields a library of structurally different amides, including value-added marketed compounds such as epsilon-caprolactam and the active pharmaceutical ingredient (API) paracetamol. This solvent-free mechanochemical procedure has also been optimized and successfully extended to several ketones serving as oxime precursors.
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hal-03166332 , version 1 (30-05-2022)

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Rita Mocci, Evelina Colacino, Lidia De Luca, Claudia Fattuoni, Andrea Porcheddu, et al.. The Mechanochemical Beckmann Rearrangement: An Eco-efficient “Cut-and-Paste” Strategy to Design the “Good Old Amide Bond”. ACS Sustainable Chemistry & Engineering, 2021, 9 (5), pp.2100-2114. ⟨10.1021/acssuschemeng.0c07254⟩. ⟨hal-03166332⟩
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