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Journal Articles Molecules Year : 2022

Mechanochemistry and Eco-Bases for Sustainable Michael Addition Reactions

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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.
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Origin : Publication funded by an institution

Dates and versions

hal-03675311 , version 1 (23-05-2022)

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Attribution - CC BY 4.0

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Yvette Lock Toy Ki, Armelle Garcia, Franck Pelissier, Tomasz Olszewski, Alicja Babst-Kostecka, et al.. Mechanochemistry and Eco-Bases for Sustainable Michael Addition Reactions. Molecules, 2022, Sustainable Chemistry in France, 27 (10), pp.3306. ⟨10.3390/molecules27103306⟩. ⟨hal-03675311⟩
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