| Title: | Comprehensive study of the organic-solvent-free CDI-mediated acylation of various nucleophiles by mechanochemistry |
| Author(s): | Metro TX; Bonnamour J; Reidon T; Duprez A; Sarpoulet J; Martinez J; Lamaty F; |
| Address: | "Institut des Biomolecules Max Mousseron (IBMM), UMR 5247, CNRS, Universite Montpellier, ENSCM, Universite de Montpellier, Campus Triolet, Place Eugene Bataillon, 34095 Montpellier Cedex 5 (France). txmetro@univ-montp2.fr. Institut des Biomolecules Max Mousseron (IBMM), UMR 5247, CNRS, Universite Montpellier, ENSCM, Universite de Montpellier, Campus Triolet, Place Eugene Bataillon, 34095 Montpellier Cedex 5 (France). Institut des Biomolecules Max Mousseron (IBMM), UMR 5247, CNRS, Universite Montpellier, ENSCM, Universite de Montpellier, Campus Triolet, Place Eugene Bataillon, 34095 Montpellier Cedex 5 (France). frederic.lamaty@univ-montp2.fr" |
| ISSN/ISBN: | 1521-3765 (Electronic) 0947-6539 (Linking) |
| 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" |
| Keywords: | acylation amides green chemistry mechanochemistry solvent-free synthesis; |
| Notes: | "PubMed-not-MEDLINEMetro, Thomas-Xavier Bonnamour, Julien Reidon, Thomas Duprez, Anthony Sarpoulet, Jordi Martinez, Jean Lamaty, Frederic eng Research Support, Non-U.S. Gov't Germany 2015/07/17 Chemistry. 2015 Sep 1; 21(36):12787-96. doi: 10.1002/chem.201501325. Epub 2015 Jul 14" |
