Simple metal salts supported on montmorillonite as recyclable catalysts for intramolecular hydroalkoxylation of double bonds in conventional and VOC-exempt solvents

Francesco, Irene Notar; Cacciuttolo, Bastien; Pucheault, Mathieu; Antoniotti, Sylvain

doi:10.1039/c4gc01990c

Cited by 21 publications

(10 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We screened a series of Lewis and Brønsted acids in a test reaction with citral and orcinol (5‐methylresorcinol), thereby focusing on the second step. The acids screened included Lewis acids such as ZnBr 2 , Ti(O i Pr) 4 , and TiCl 4 ; solid catalysts such as Amberlyst and zeolite; and montmorillonite‐doped with metal cations (M‐MMT), a type of solid catalyst that we recently used as a Lewis acid in C–O and C–C bond‐forming processes . The most interesting results are summarized in Table (see Supporting Information for additional examples).…”

Section: Resultsmentioning

confidence: 99%

Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All‐Catalytic Synthesis of (±)‐ortho‐Tetrahydrocannabinols and Analogues from Natural Feedstocks

et al. 2018

Self Cite

View full text Add to dashboard Cite

Using a combination of Au nanoparticle‐catalyzed oxidation under an O2 atmosphere and a Ti‐doped montmorillonite (Ti‐MMT)‐catalyzed tandem arylation/double cyclization, we developed an original and highly selective method for the synthesis of ortho‐tetrahydrocannabinol derivatives from simple substrates. The reaction sequence could be performed in two steps in batch mode or in a single operation in continuous‐flow reactors. The abnormal regioselectivity was proposed to be the result of the non‐innocent role of the MMT support, TiIV cation coordination, and a Lewis acid‐assisted Brønsted acid (LBA) mechanism.

show abstract

Section: Resultsmentioning

confidence: 99%

Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All‐Catalytic Synthesis of (±)‐ortho‐Tetrahydrocannabinols and Analogues from Natural Feedstocks

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…Many of these materials, however, suffer from challenges around high toxicity or high cost. There has therefore been interest in the application of iron salts to overcome these challenges. − The first studies on heterogeneous iron catalysts were presented in 2015 by Antoniotti et al These employed montmorillonite-supported iron, achieving yields of up to 86% for the hydroalkoxylation of 5-methyl-2,2-diphenyl-4-hexen-1-ol to 2,2-dimethyl-5,5-diphenyltetrahydro-2H-pyran in dimethyl carbonate (DMC) as a solvent. The further development of low-cost, active, heterogeneous catalysts based on earth-abundant materials remains a desirable objective.…”

Section: Results and Discussionmentioning

confidence: 99%

Hydrothermal Synthesis of Biomass-Derived Magnetic Carbon Composites for Adsorption and Catalysis

Davies

McGregor

2021

ACS Omega

View full text Add to dashboard Cite

The synthesis of magnetic iron–carbon composites (Fe/C) from waste avocado seeds via hydrothermal carbonization (HTC) has been demonstrated for the first time. These materials are shown to be effective in adsorption and catalytic applications, with performances comparable to or higher than materials produced through conventional processing routes. Avocado seeds have been processed in high-temperature water (230 °C) at elevated pressure (30 bar at room temperature) in the presence of iron nitrate and iron sulfate, in a process mimicking natural coalification. Characterization of the synthesized material has been carried out by X-ray diffraction (XRD), atomic absorption spectroscopy (AAS), X-ray fluorescence (XRF), X-ray photoelectron spectroscopy (XPS), inductively coupled plasma-optical emission spectrometry (ICP-OES), Fourier-transform infrared spectroscopy (FT-IR), magnetometry, and through surface area measurements. The supported iron particles are observed to be predominately magnetite, with an oxidized hematite surface region. The presence of iron catalyzes the formation of an extended, ordered polymeric structure in the avocado seed-derived carbon. The magnetic Fe/C has been demonstrated as an adsorbent for environmental wastewater treatment using methylene blue and indigo carmine. Kinetic analysis suggests that the adsorbates are chemisorbed, with the positive surface charge of Fe/C being preferential for indigo carmine adsorption (49 mg g–1). Additionally, Fe/C has been evaluated as a heterogeneous catalyst for the hydroalkoxylation of phenylacetylene with ethylene glycol to 2-benzyl-1,3-dioxolane. Product yields of 45% are obtained, with 100% regioselectivity to the formed isomer. The solid catalyst has the advantages of being prepared from a waste material and of easy removal after reaction via magnetic separation. These developments provide opportunities to produce carbon-based materials for a variety of high-value applications, potentially also including energy storage and biopharmaceuticals, from a wide range of lignocellulosic biomass feedstocks.

show abstract

“…Iron (III) chloride can also be supported on montmorillonite as natural inorganic material to provide a very effective heterogeneous and reusable catalyst for this process. In 2015, the supported Fe-MMT catalyst developed by Antoniotti et al showed good activity and selectivity at 80 • C in dimethyl carbonate (DMC) for the cyclization of alkenols with various substitution patterns on the alkene moiety (Figure 2) [49,50]. This heterogeneous catalyst, which can be reused several times without loss of activity, displays higher activity and selectivity than those of reactions carried out under homogeneous catalysis.…”

Section: Hydroalkoxylationmentioning

confidence: 99%

Earth-Abundant 3d Transition Metal Catalysts for Hydroalkoxylation and Hydroamination of Unactivated Alkenes

et al. 2021

View full text Add to dashboard Cite

show abstract

Simple metal salts supported on montmorillonite as recyclable catalysts for intramolecular hydroalkoxylation of double bonds in conventional and VOC-exempt solvents

Abstract: We describe herein an efficient and particularly sustainable catalytic system for the intramolecular hydroalkoxylation of double bonds.

Cited by 21 publications

References 34 publications

Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All‐Catalytic Synthesis of (±)‐ortho‐Tetrahydrocannabinols and Analogues from Natural Feedstocks

Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All‐Catalytic Synthesis of (±)‐ortho‐Tetrahydrocannabinols and Analogues from Natural Feedstocks

Hydrothermal Synthesis of Biomass-Derived Magnetic Carbon Composites for Adsorption and Catalysis

Earth-Abundant 3d Transition Metal Catalysts for Hydroalkoxylation and Hydroamination of Unactivated Alkenes

Contact Info

Product

Resources

About