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Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants

  • Combining Phytoextraction and Ecological Catalysis: an Environmental, Ecological, Ethic and Economic Opportunity
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Abstract

Among the phytotechnologies used for the reclamation of degraded mining sites, phytoextraction aims to diminish the concentration of polluting elements in contaminated soils. However, the biomass resulting from the phytoextraction processes (highly enriched in polluting elements) is too often considered as a problematic waste. The manganese-enriched biomass derived from native Mn-hyperaccumulating plants of New Caledonia was presented here as a valuable source of metallic elements of high interest in chemical catalysis. The preparation of the catalyst Eco-Mn1 and reagent Eco-Mn2 derived from Grevillea exul exul and Grevillea exul rubiginosa was investigated. Their unusual polymetallic compositions allowed to explore new reactivity of low oxidative state of manganese—Mn(II) for Eco-Mn1 and Mn(IV) for Eco-Mn2. Eco-Mn1 was used as a Lewis acid to catalyze the acetalization/elimination of aldehydes into enol ethers with high yields; a new green and stereoselective synthesis of (−)-isopulegol via the carbonyl-ene cyclization of (+)-citronellal was also performed with Eco-Mn1. Eco-Mn2 was used as a mild oxidative reagent and controlled the oxidation of aliphatic alcohols into aldehydes with quantitative yields. Oxidative cleavage was interestingly noticed when Eco-Mn2 was used in the presence of a polyol. Eco-Mn2 allowed direct oxidative iodination of ketones without using iodine, which is strongly discouraged by new environmental legislations. Finally, the combination of the properties in the Eco-Mn catalysts and reagents gave them an unprecedented potential to perform sequential tandem oxidation processes through new green syntheses of p-cymene from (−)-isopulegol and (+)-citronellal; and a new green synthesis of functionalized pyridines by in situ oxidation of 1,4-dihydropyridines.

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Acknowledgments

The authors would like to thank the Agence Nationale de la Recherche (ANR, programme 11ECOT 011 01), the Agence de l’Environnement et de la Maîtrise de l’Energie (ADEME), the Centre National de la Recherche Scientifique (CNRS) and the Fond Européen de Développement Régional (FEDER) for financial support.

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  1. Laboratoire de Chimie bio inspirée et Innovations écologiques, FRE 3673 ChimEco CNRS-UM2, Stratoz, Cap Alpha-Avenue de l’Europe, Clapiers, 34830, Montpellier, France

    Vincent Escande, Brice-Loïc Renard & Claude Grison

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  1. Vincent Escande
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  2. Brice-Loïc Renard
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  3. Claude Grison
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Correspondence to Claude Grison.

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Responsible editor: Philippe Garrigues

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Escande, V., Renard, BL. & Grison, C. Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants. Environ Sci Pollut Res 22, 5633–5652 (2015). https://doi.org/10.1007/s11356-014-3631-z

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  • DOI: https://doi.org/10.1007/s11356-014-3631-z

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