Trans-ferulic acid valorization into stilbene derivatives via tandem decarboxylation/Heck coupling using Pd/Al-SBA-15 materials

Maties, Georgiana; González‐Arellano, Camino; Luque, Rafael; Montejano-Nares, E.; Ivars‐Barceló, Francisco; Pineda, Antonio

doi:10.1016/j.mtchem.2022.100971

Cited by 4 publications

(4 citation statements)

References 41 publications

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“…Mesoporous silica materials, which have ordered pore size, a high specific surface area, a large pore volume, and the ability to synthesize a wide range of morphologies and shapes, can be utilized as an alternative to zeolites [110][111][112][113][114][115][116]. Mesoporous silica, such as MCM-41 and SBA-15, used as supports for metal NPs and widely applied in catalysis, including tandem processes.…”

Section: Heterogeneous Pd-catalyzed Tandem Processesmentioning

confidence: 99%

“…It is noteworthy that the reaction products can be used as a renewable biosolvent and biofuel precursors. Maties et al [116] synthesized Pd-containing Al-SBA-15 materials for the valorization of trans-ferulic acid into stilbenes via tandem decarboxylation/Mizoroki-Heck coupling (Figure 51). Under mild reaction conditions (100 • C, 3-6 h), quantitative product yields were obtained with over 90% selectivity to target stilbene products.…”

Section: Heterogeneous Pd-catalyzed Tandem Processesmentioning

confidence: 99%

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Recent Progress in Pd-Catalyzed Tandem Processes

Nikoshvili

Matveeva

2023

Catalysts

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In recent years, Pd-containing catalytic systems for tandem processes have gained special attention due to their enhanced catalytic properties and their possibility of performing several reactions without the necessity of separating the intermediates. In this review, recent progress in Pd-catalyzed tandem processes is considered. Three types of catalytic systems are described: homogeneous catalysts (including immobilized Pd complexes); heterogeneous catalysts supported on oxides, MOFs, COFs, etc., with particular attention to the supports containing acid/base sites; and metal-enzyme catalysts for chemoenzymatic tandem processes applied in fine organic synthesis and biotechnology. For homogeneous Pd-catalyzed reactions, different tandem reactions were considered, i.e., cross-coupling, cyclization, carbonylation, isomerization, alkylation, arylation, etc.

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Section: Heterogeneous Pd-catalyzed Tandem Processesmentioning

confidence: 99%

Section: Heterogeneous Pd-catalyzed Tandem Processesmentioning

confidence: 99%

Recent Progress in Pd-Catalyzed Tandem Processes

Nikoshvili

Matveeva

2023

Catalysts

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“…Among the mesoporous silica family of materials, SBA-15 with 2D hexagonally arranged ordered mesoporous silica has attracted special attention over the years due to their high internal surface area, large pore volume, ease of surface functionalization, and high hydrothermal stability . Functionalized SBA-15 materials are largely employed as catalyst supports through hosting metal ions/metallic nanoparticles. , Though transition-metal-grafted SBA-15 materials are widely utilized as heterogeneous catalysts for several organic transformations, − only a few transition-metal-grafted functionalized SBA-15 materials are reported for colorimetric − and electrochemical sensing of toxic pollutants. − The first-row transition-metal immobilization over the surface of SBA-15 is generally achieved through post-synthetic wet impregnation or organic functionalization. These post-synthetic modifications often lead to reduced surface area and pore blockage.…”

Section: Introductionmentioning

confidence: 99%

Copper Immobilized over 2D Hexagonal SBA-15 for Electrochemical and Colorimetric Sulfite Sensing

et al. 2023

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Sulfite (SO 3 2−) is considered a highly toxic anion for living organisms. Herein, we report the synthesis of copper immobilized over a 2D hexagonally ordered mesoporous silica material CuMS as an electrochemical and colorimetric dual-technique-based sensing platform for sulfite detection. The immobilization of copper on silica was achieved through the bis[3-(triethoxysilyl)propyl]tetrasulfide (TEPTS) ligand. Morphological and physical properties of the material were confirmed by several characterization techniques, including scanning electron microscopy, transmission electron microscopy, X-ray diffraction, N 2 sorption, and X-ray photoelectron spectroscopy. The CuMS material retained mesoporosity with a narrow pore size distribution (D ≈ 5.4 nm) and a high Brunauer−Emmett−Teller surface area of 682 m 2 g −1 after the immobilization of copper. The prepared catalyst shows promising electrocatalytic activity toward sulfite oxidation. A linear variation in the peak current was obtained for SO 3 2− oxidation in the 0.2−15 mM range with a high sensitivity of 62.08 μA cm −2 , under optimum experimental conditions. The limit of detection (LOD) was found to be 1.14 nM. CuMS also shows excellent activity toward colorimetric detection of sulfite anions with an LOD of 0.4 nM. The proposed sensor shows high selectivity toward the sulfite anion, even in the presence of common interferents. The detection of sulfite in white wine with excellent recovery demonstrates the practical applicability of this sensor.

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“…Among the many methods, a palladium-catalyzed cross-coupling Mizoroki–Heck reaction has played a key role since it is widely used in different synthetic areas, i.e., pharmaceuticals, , fine chemicals, and organic semiconductors . Furthermore, slight modification of reaction conditions may also allow a consecutive series of Mizoroki–Heck reactions, − obtaining synthetic advantages in terms of step-economy …”

Section: Introductionmentioning

confidence: 99%

Tailor-Made POLITAG-Pd⁰ Catalyst for the Low-Loading Mizoroki–Heck Reaction in γ-Valerolactone as a Safe Reaction Medium

Valentini

Carpisassi

Comès

et al. 2022

ACS Sustainable Chem. Eng.

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In this contribution, we have reported our study on the fine-tuned design and synthesis of new POLITAGs-Pd0 (POLymeric Ionic TAG) catalytic systems with the intention of defining highly efficient heterogeneous palladium catalysts stabilized by ionic tags able to operate at a very low loading while being fully recoverable/reusable. By varying both the support and the ratio between the metal and immobilized ionic tag, we have accessed five different heterogeneous catalytic systems that have been fully characterized (EA, XPS, TEM, and HR-TEM) to investigate their morphological differences. The catalytic efficiency of the newly prepared POLITAGs-Pd0 materials was then tested and compared in the representative Mizoroki–Heck cross-coupling reaction, a universally investigated and widely useful process. A close correlation between the catalyst support and catalytic performances has been highlighted. The best system POLITAG-Pd0-HM features a high TOF value (26,786 h–1), affording the final products in high isolated yields by using as little as only 0.0007 mol % of Pd. Moreover, this high catalytic activity coupled with the use of γ-valerolactone (GVL) as a green reaction medium has led to the definition of a very efficient waste-minimized protocol. The newly designed catalyst has been utilized in the representative synthesis of Amiloxate, a widely used sunscreen agent, that could be prepared with negligible metal contamination and very low E-factor.

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Trans-ferulic acid valorization into stilbene derivatives via tandem decarboxylation/Heck coupling using Pd/Al-SBA-15 materials

Cited by 4 publications

References 41 publications

Recent Progress in Pd-Catalyzed Tandem Processes

Recent Progress in Pd-Catalyzed Tandem Processes

Copper Immobilized over 2D Hexagonal SBA-15 for Electrochemical and Colorimetric Sulfite Sensing

Tailor-Made POLITAG-Pd⁰ Catalyst for the Low-Loading Mizoroki–Heck Reaction in γ-Valerolactone as a Safe Reaction Medium

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Trans-ferulic acid valorization into stilbene derivatives via tandem decarboxylation/Heck coupling using Pd/Al-SBA-15 materials

Cited by 4 publications

References 41 publications

Recent Progress in Pd-Catalyzed Tandem Processes

Recent Progress in Pd-Catalyzed Tandem Processes

Copper Immobilized over 2D Hexagonal SBA-15 for Electrochemical and Colorimetric Sulfite Sensing

Tailor-Made POLITAG-Pd0 Catalyst for the Low-Loading Mizoroki–Heck Reaction in γ-Valerolactone as a Safe Reaction Medium

Contact Info

Product

Resources

About

Tailor-Made POLITAG-Pd⁰ Catalyst for the Low-Loading Mizoroki–Heck Reaction in γ-Valerolactone as a Safe Reaction Medium