An environmentally friendly, photocontrollable and highly recyclable catalyst for use in a one-pot three-component Mannich reaction

Tang, Qian; Quan, Hong-jiang; Liu, Song; Liu, Lantao; Chow, Cheuk Fai Stephen; Gong, Cheng-Bin

doi:10.1016/j.molcata.2016.05.006

Cited by 6 publications

(2 citation statements)

References 53 publications

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“…Very recently, Chow, Gong and co-workers reported the synthesis of a photocontrollable and highly recyclable catalyst, ZrOPPAZOSO 3 H, through the immobilization of 4-[4-(6phosphonic acid hexanoxyl)phenylazo]benzenesulfonic acid on zirconium phosphonate (Scheme 150). 650 This catalyst was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray powder diffraction, Several supported LASCs have also been developed. Kobayashi and co-workers reported the first example of a polymer-supported Lewis acid catalyst by changing the hydrophobic surfactant part of a LASC to polymer chains with "spacers" composed of alkyl aromatic moieties.…”

Section: Surfactant-combined Catalystsmentioning

confidence: 99%

“…Very recently, Chow, Gong and co-workers reported the synthesis of a photocontrollable and highly recyclable catalyst, ZrOPPAZOSO 3 H, through the immobilization of 4-[4-(6-phosphonic acid hexanoxyl)phenylazo]benzenesulfonic acid on zirconium phosphonate (Scheme ). This catalyst was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray powder diffraction, nitrogen adsorption–desorption analyses, and UV–vis analyses. The catalytic activity of ZrOPPAZOSO 3 H was investigated in the one-pot, three-component Mannich-type reaction of benzaldehyde, aniline, and cyclohexanone in water at room temperature, and gave excellent yields.…”

Section: Surfactant-based Catalystsmentioning

confidence: 99%

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Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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Traditional organic synthesis relies heavily on organic solvents for a multitude of tasks, including dissolving the components and facilitating chemical reactions, because many reagents and reactive species are incompatible or immiscible with water. Given that they are used in vast quantities as compared to reactants, solvents have been the focus of environmental concerns. Along with reducing the environmental impact of organic synthesis, the use of water as a reaction medium also benefits chemical processes by simplifying operations, allowing mild reaction conditions, and sometimes delivering unforeseen reactivities and selectivities. After the "watershed" in organic synthesis revealed the importance of water, the development of water-compatible catalysts has flourished, triggering a quantum leap in water-centered organic synthesis. Given that organic compounds are typically practically insoluble in water, simple extractive workup can readily separate a water-soluble homogeneous catalyst as an aqueous solution from a product that is soluble in organic solvents. In contrast, the use of heterogeneous catalysts facilitates catalyst recycling by allowing simple centrifugation and filtration methods to be used. This Review addresses advances over the past decade in catalytic reactions using water as a reaction medium.

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Section: Surfactant-combined Catalystsmentioning

confidence: 99%

“…Very recently, Chow, Gong and co-workers reported the synthesis of a photocontrollable and highly recyclable catalyst, ZrOPPAZOSO 3 H, through the immobilization of 4-[4-(6-phosphonic acid hexanoxyl)phenylazo]benzenesulfonic acid on zirconium phosphonate (Scheme ). This catalyst was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray powder diffraction, nitrogen adsorption–desorption analyses, and UV–vis analyses. The catalytic activity of ZrOPPAZOSO 3 H was investigated in the one-pot, three-component Mannich-type reaction of benzaldehyde, aniline, and cyclohexanone in water at room temperature, and gave excellent yields.…”

Section: Surfactant-based Catalystsmentioning

confidence: 99%

Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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Three‐Component Mannich Reaction Catalyzed by Mesostructured Cellular Foam Silica Immobilized H₃PW₁₂O₄₀

et al. 2019

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One-pot three-component Mannich reaction was carried out at room temperature using mesocellular cellular foam (MCF) silica loaded H 3 PW 12 O 40 as catalyst. The H 3 PW 12 O 40 /MCF catalyst was prepared by the traditional impregnation method and confirmed by a series of characterizations such as nitrogen adsorption, X-ray diffraction (XRD), Fourier-transform infrared spectra (FT-IR), scanning electron microscope (SEM) and transmission electron microscopy (TEM). The results showed that the H 3 PW 12 O 40 /MCF catalyst with 50 wt% loading of H 3 PW 12 O 40 exhibited the highest catalytic activity for the Mannich reaction of benzaldehyde, aniline and acetophenone with the yield of 94% in 1.8 hours under the optimal condition. In addition, the H 3 PW 12 O 40 /MCF catalyst could be easily recycled and reused four times without significant decline of activity. This work provided an improved modification of the three-component Mannich reaction in terms of efficient activity, mild reaction conditions, clean reaction profiles and a simple workup procedure.

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An amphiphilic and photoswitchable organocatalyst for the aldol reaction based on a product-imprinted polymer

Zheng

Gong

Zhang

et al. 2017

Molecular Catalysis

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An environmentally friendly, photocontrollable and highly recyclable catalyst for use in a one-pot three-component Mannich reaction

Cited by 6 publications

References 53 publications

Catalytic Organic Reactions in Water toward Sustainable Society

Catalytic Organic Reactions in Water toward Sustainable Society

Three‐Component Mannich Reaction Catalyzed by Mesostructured Cellular Foam Silica Immobilized H₃PW₁₂O₄₀

An amphiphilic and photoswitchable organocatalyst for the aldol reaction based on a product-imprinted polymer

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An environmentally friendly, photocontrollable and highly recyclable catalyst for use in a one-pot three-component Mannich reaction

Cited by 6 publications

References 53 publications

Catalytic Organic Reactions in Water toward Sustainable Society

Catalytic Organic Reactions in Water toward Sustainable Society

Three‐Component Mannich Reaction Catalyzed by Mesostructured Cellular Foam Silica Immobilized H3PW12O40

An amphiphilic and photoswitchable organocatalyst for the aldol reaction based on a product-imprinted polymer

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Product

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Three‐Component Mannich Reaction Catalyzed by Mesostructured Cellular Foam Silica Immobilized H₃PW₁₂O₄₀