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

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

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.

Original languageEnglish (US)
Article number3075
JournalMolecules
Volume27
Issue number10
DOIs
StatePublished - May 1 2022

Keywords

  • aldehydes
  • biomass
  • green chemistry
  • hydrophosphonylation
  • hydroxyphosphonates

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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