Green and Effective Preparation of α-Hydroxyphosphonates by Ecocatalysis
Pola Cybulska,
Yves-Marie Legrand,
Alicja Babst-Kostecka,
Sébastien Diliberto,
Anna Leśniewicz,
Erwan Oliviero,
Valérie Bert,
Clotilde Boulanger,
Claude Grison,
Tomasz K. Olszewski
Affiliations
Pola Cybulska
Department of Physical and Quantum Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
Yves-Marie Legrand
Bio-Inspired Chemistry and Ecological Innovations (ChimEco), UMR 5021 CNRS, University of Montpellier, Cap Delta, 1682 rue de la Valsière, 34790 Grabels, France
Alicja Babst-Kostecka
Department of Environmental Science, The University of Arizona, Tucson, AZ 85721, USA
Sébastien Diliberto
Institut Jean Lamour, UMR 7198 CNRS, University of Lorraine, 57000 Metz, France
Anna Leśniewicz
Analytical Chemistry and Chemical Metallurgy Division, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
Erwan Oliviero
ICGM, University of Montpellier, CNRS, 34090 Montpellier, France
Valérie Bert
Clean Technologies and Circular Economy Unit, SIT Department, INERIS, Parc Technologique Alata BP 2, 60550 Verneuil en Halatte, France
Clotilde Boulanger
Institut Jean Lamour, UMR 7198 CNRS, University of Lorraine, 57000 Metz, France
Claude Grison
Bio-Inspired Chemistry and Ecological Innovations (ChimEco), UMR 5021 CNRS, University of Montpellier, Cap Delta, 1682 rue de la Valsière, 34790 Grabels, France
Tomasz K. Olszewski
Department of Physical and Quantum Chemistry, Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland
A green and effective approach for the synthesis of structurally diversed α-hydroxyphosphonates via hydrophosphonylation of aldehydes under solventless conditions and promoted by biosourced catalysts, called ecocatalysts “Eco-MgZnOx” is presented. Ecocatalysts were prepared from Zn-hyperaccumulating plant species Arabidopsis halleri, with simple and benign thermal treatment of leaves rich in Zn, and without any further chemical treatment. The elemental composition and structure of Eco-MgZnOx were characterized by MP–AES, XRPD, HRTEM, and STEM–EDX techniques. These analyses revealed a natural richness in two unusual and valuable mixed zinc–magnesium and iron–magnesium oxides. The ecocatalysts were employed in this study to demonstrate their potential use in hydrophosphonylation of aldehydes, leading to various α-hydroxyphosphonate derivatives, which are critical building blocks in the modern chemical industry. Computational chemistry was performed to help discriminate the role of some of the constituents of the mixed oxide ecocatalysts. High conversions, broad substrate scope, mild reaction conditions, and easy purification of the final products together with simplicity of the preparation of the ecocatalysts are the major advantages of the presented protocol. Additionally, Eco-MgZnOx-P could be recovered and reused for up to five times.