NDLI: Comprehensive Study of the Organic-Solvent-Free CDI-Mediated Acylation of Various Nucleophiles by $Mechanochemistry^{†}$

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Lamaty, Frédéric Martinez, Jean Bonnamour, Julien Duprez, Anthony Reidon, Thomas Sarpoulet, Jordi Métro, Thomas-xavier
Description	Author Affiliation: Métro TX ( Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Campus Triolet, Place Eugène Bataillon, 34095 Montpellier Cedex 5 (France). txmetro@univ-montp2.fr.); Bonnamour J ( Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Campus Triolet, Place Eugène Bataillon, 34095 Montpellier Cedex 5 (France).); Reidon T ( Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Campus Triolet, Place Eugène Bataillon, 34095 Montpellier Cedex 5 (France).); Duprez A ( Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Campus Triolet, Place Eugène Bataillon, 34095 Montpellier Cedex 5 (France).); Sarpoulet J ( Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Campus Triolet, Place Eugène Bataillon, 34095 Montpellier Cedex 5 (France).); Martinez J ( Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Campus Triolet, Place Eugène Bataillon, 34095 Montpellier Cedex 5 (France).); Lamaty F ( Institut des Biomolécules Max Mousseron (IBMM), UMR 5247, CNRS, Université Montpellier, ENSCM, Université de Montpellier, Campus Triolet, Place Eugène Bataillon, 34095 Montpellier Cedex 5 (France). frederic.lamaty@univ-montp2.fr.)
Abstract	Acylation reactions are ubiquitous in the synthesis of natural products and biologically active compounds. Unfortunately, these reactions often require the use of large quantities of volatile and/or toxic solvents, either for the reaction, purification or isolation of the products. Herein we describe and discuss the possibility of completely eliminating the use of organic solvents for the synthesis, purification and isolation of products resulting from the acylation of amines and other nucleophiles. Thus, utilisation of N,N′-carbonyldiimidazole (CDI) allows efficient coupling between carboxylic acids and various nucleophiles under solvent-free mechanical agitation, and water-assisted grinding enables both the purification and isolation of pure products. Critical parameters such as the physical state and water solubility of the products, milling material, type of agitation (vibratory or planetary) as well as contamination from wear are analysed and discussed. In addition, original organic-solvent-free conditions are proposed to overcome the limitations of this approach. The calculations of various green metrics are included, highlighting the particularly low environmental impact of this strategy.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	36
Volume Number	21
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2015-09-01
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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