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© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.

Abstract

The Michael addition reaction was revisited with a full focus on sustainability combined with efficiency, using mechanochemistry in mild conditions. First, the synthesis of cyclopentenone derivatives was chosen as a model reaction to find optimal conditions in mechanochemistry while using classical but weak bases. The reaction was efficient (84–95% yields), fast (2–6 h), solvent free, and required 0.1 equivalent of base. Aiming to reach greener conditions, classical bases were then replaced using new bio-sourced bases, called Eco-bases, that were easily prepared from plants and led to heterogeneous catalysts. The composition and structure of Eco-bases were characterized by MP-AES, XRPD, EBSD/EDS, HRTEM/EDX and ion chromatography. Interestingly, a high ratio of potassium was observed with the presence of K2Ca(CO3)2 for the most effective Eco-base. The new Eco-bases were used for the mechanical-assisted construction of functionalized alkenone derivatives. The versatility of the method has been successfully applied with good to excellent yields to different Michael donors and acceptors. Eco-bases were recycled and reused four times with the same performances. Combining Eco-bases and mechanochemistry in Michael addition reactions allowed reaching a maximum degree of sustainability (efficient, rapid, low catalyst loading, solvent-free reactions with bio-sourced catalysts) and participating in the development of mechanochemistry in sustainable chemistry.

Details

Title
Mechanochemistry and Eco-Bases for Sustainable Michael Addition Reactions
Author
Yvette Lock Toy Ki 1   VIAFID ORCID Logo  ; Garcia, Armelle 1 ; Pelissier, Franck 1 ; Olszewski, Tomasz K 2   VIAFID ORCID Logo  ; Babst-Kostecka, Alicja 3   VIAFID ORCID Logo  ; Legrand, Yves-Marie 1   VIAFID ORCID Logo  ; Grison, Claude 1   VIAFID ORCID Logo 

 Laboratory of Bio-inspired Chemistry and Ecological Innovations (ChimEco), UMR 5021, CNRS, University of Montpellier, Cap Delta, 1682 rue de la Valsière, 34790 Grabels, France; [email protected] (Y.L.T.K.); [email protected] (A.G.); [email protected] (F.P.); [email protected] (Y.-M.L.) 
 Department of Physical and Quantum Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, Wybrzeze Wyspianskiego 29, 50-370 Wroclaw, Poland; [email protected] 
 Department of Environmental Science, The University of Arizona, 1110 E. South Campus Drive, Saguaro Hall, Building 33, Tucson, AZ 85721, USA; [email protected] 
First page
3306
Publication year
2022
Publication date
2022
Publisher
MDPI AG
e-ISSN
14203049
Source type
Scholarly Journal
Language of publication
English
ProQuest document ID
2670328262
Copyright
© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.