New biomaterials for Ni biosorption turned into catalysts for Suzuki–Miyaura cross coupling of aryl iodides in green conditions

Cases, Lucie; Adler, Pauline; Pélissier, Franck; Diliberto, Sébastien; Boulanger, Clotilde; Grison, Claude

doi:10.1039/d1ra04478h

Cited by 7 publications

(3 citation statements)

References 27 publications

(39 reference statements)

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“…The Grison group has shown that the remediation phytotechnologies, such as phytoextraction [ 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ], rhizofiltration [ 28 , 29 , 30 , 31 ] and biosorption [ 32 , 33 , 34 , 35 , 36 ] generate biomass which can be turned into innovative ecocatalysts. Among the plant species that can be transformed, here, we selected the ones that were the richest in potassium ( Figure 1 ).…”

Section: Resultsmentioning

confidence: 99%

Mechanochemistry and Eco-Bases for Sustainable Michael Addition Reactions

Garcia

Pélissier

et al. 2022

Molecules

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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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Section: Resultsmentioning

confidence: 99%

Mechanochemistry and Eco-Bases for Sustainable Michael Addition Reactions

Garcia

Pélissier

et al. 2022

Molecules

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“…This innovative methodology is based on the use of biomass derived from metal-hyperaccumulating plants, used in the phytoextraction of metal contaminated sites, for the preparation of polymetallic catalysts suitable for applications in organic synthesis. This concept was successfully applied for important transformations such as the Lewis and/or Brønsted acid-catalyzed reactions (Diels–Alder reaction, Friedel–Crafts reaction, multicomponent reactions, cascade reactions) [ 54 , 55 , 56 , 57 , 58 ]; coupling reactions (Suzuki, Heck, Sonogashira and Ulmann type reactions) [ 59 , 60 , 61 , 62 , 63 , 64 ]; reductions (aminoreduction, selective reduction of αβ-unsaturated carbonyl compounds, nitro- and halogeno arenes) [ 65 , 66 , 67 ]; oxidations (epoxidations, oxidative cleavage, oxidations of alcohols) [ 68 , 69 , 70 ]; and tandem reactions (tandem carbonyl-ene cyclization, synthesis of substituted pyridines and oxidative iodination of ketones) [ 71 , 72 , 73 ]. However, examples on the use of ecocatalysis for C-P bond formation have not been reported.…”

Section: Introductionmentioning

confidence: 99%

Green and Effective Preparation of α-Hydroxyphosphonates by Ecocatalysis

et al. 2022

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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.

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“…The Grison group has shown that remediation phytotechnologies, such as phytoextraction [ 30 , 31 , 32 ], rhizofiltration [ 33 , 34 , 35 ] and biosorption [ 35 , 36 , 37 , 38 ], generate biomass rich in transition metals that can be turned into innovative catalysts, called ecocatalysts [ 39 , 40 , 41 ]. Using the concept of ecocatalysis, we advanced the aim that only natural or biosourced catalysts would be used for preparing the cyclic oxyterpenes.…”

Section: Introductionmentioning

confidence: 99%

New Sustainable Synthetic Routes to Cyclic Oxyterpenes Using the Ecocatalyst Toolbox

et al. 2021

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Cyclic oxyterpenes are natural products that are mostly used as fragrances, flavours and drugs by the cosmetic, food and pharmaceutical industries. However, only a few cyclic oxyterpenes are accessible via chemical syntheses, which are far from being ecofriendly. We report here the synthesis of six cyclic oxyterpenes derived from ß-pinene while respecting the principles of green and sustainable chemistry. Only natural or biosourced catalysts were used in mild conditions that were optimised for each synthesis. A new generation of ecocatalysts, derived from Mn-rich water lettuce, was prepared via green processes, characterised by MP-AES, XRPD and TEM analyses, and tested in catalysis. The epoxidation of ß-pinene led to the platform molecule, ß-pinene oxide, with a good yield, illustrating the efficacy of the new generation of ecocatalysts. The opening ß-pinene oxide was investigated in green conditions and led to new and regioselective syntheses of myrtenol, 7-hydroxy-α-terpineol and perillyl alcohol. Successive oxidations of perillyl alcohol could be performed using no hazardous oxidant and were controlled using the new generation of ecocatalysts generating perillaldehyde and cuminaldehyde.

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New biomaterials for Ni biosorption turned into catalysts for Suzuki–Miyaura cross coupling of aryl iodides in green conditions

Abstract: New biomaterials were functionalised for biosorption of Ni from aqueous solutions and valorised as ecocatalysts in Suzuki–Miyaura green reactions.

Cited by 7 publications

References 27 publications

Mechanochemistry and Eco-Bases for Sustainable Michael Addition Reactions

Mechanochemistry and Eco-Bases for Sustainable Michael Addition Reactions

Green and Effective Preparation of α-Hydroxyphosphonates by Ecocatalysis

New Sustainable Synthetic Routes to Cyclic Oxyterpenes Using the Ecocatalyst Toolbox

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