Imprint of free space around acid site in hollow mesoporous polymeric solid acid and application in heterogeneous acetal hydrolysis/asymmetric aldol tandem reaction

Bo, Yanan; Wang, Xuri; Deng, Xintao; Ma, Xuebing

doi:10.1016/j.apcata.2019.117360

Cited by 15 publications

(1 citation statement)

References 57 publications

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“…Insofar as hydrothermal stability is concerned, the applications of POPs have already been exemplified for divergent heterogeneous catalytic reactions as well as supports for catalysts. [12][13][14][15][16] A survey of the literature reveals that the number of POPs reported as organocatalysts when compared to those as supports of metal nanoparticles [17][18][19] is limited. There is an incessant quest to develop novel metal-free catalysts that not only display the advantages of homogeneous catalysts in terms of catalytic activity, mild reaction conditions, etc.…”

Section: Introductionmentioning

confidence: 99%

Porous Organic Polymer with Free Carboxylic Acids (Carboxy‐POP) for Heterogeneous Catalytic One‐Pot Synthesis of Xanthenes and Acridines

Karn,

Yadav,

Kumar Sahoo

et al. 2023

ChemCatChem

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Porous organic polymers (POPs) – the emergent hydrothermally stable, amorphous and porous materials – have proven to be invaluable for catalytic applications. Through a rational bottom‐up design, we have developed a Carboxy‐POP, a POP that is adorned by Bronsted acid (COOH) functionalities, for heterogeneous catalysis. The Carboxy‐POP has been comprehensively characterized by FT‐IR, solid‐state 13C NMR, SEM, TEM, etc. It exhibits a moderate porosity with a BET surface area of 381 m2 g‐1 and acidic concentration of 1.67 mmol/g. Its functional utility as an efficient heterogeneous catalyst for one‐pot synthesis of a variety of xanthenes and acridines in excellent isolated yields (up to 90%) is demonstrated. In contrast to the conventional methods, the advantages of the reported metal‐free catalytic protocol include ease of operation, excellent isolated yields of the products, facile workup, and shorter reaction times. It is shown that the heterogeneous catalyst can be repetitively used with the catalytic activity almost intact even after 16 reaction cycles.

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Section: Introductionmentioning

confidence: 99%

Porous Organic Polymer with Free Carboxylic Acids (Carboxy‐POP) for Heterogeneous Catalytic One‐Pot Synthesis of Xanthenes and Acridines

Karn,

Yadav,

Kumar Sahoo

et al. 2023

ChemCatChem

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“Ship‐in‐a‐Bottle” Strategy for Immobilization of 9‐Amino(9‐deoxy)epi‐Cinchona Alkaloid into Molecularly Imprinted Solid Acid: Acetal Hydrolysis/Asymmetric Aldol Tandem Reaction

Wei

Zhang

et al. 2020

ChemCatChem

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Direct immobilization of versatile 9‐amino(9‐deoxy)epi‐cinchona alkaloids without molecule modification to achieve heterogeneous organocatalysis is of interest in the low‐cost production of optically active compounds. In this paper, an exquisite “ship‐in‐a‐bottle” strategy for direct and simple immobilization of 9‐amino‐(9‐deoxy)epi‐quinine (QNNH2) into hollow polystyrene nano‐bowl with imprinted free space around −SO3H was developed via acid‐base reaction and radical polymerization. The heterogeneous organocatalyst with 0.44 mmol g−1 of QNNH2 and 0.48 mmol g−1 of residual −SO3H possessed fast mass transfer due to the characteristic architectural features, such as thin shell thickness, free space around catalytic site, and hollow interior. In heterogeneous acetal hydrolysis/asymmetric aldol tandem reaction, good to excellent catalytic performances (90–95 % yields, anti/syn=88/12–96/4, and 97–99 % ee anti) for acetals bearing electron‐withdrawing substituents (R=o, m, p‐NO2, Cl) were achieved. The “ship‐in‐a‐bottle” QNNH2 displayed good stability and reusability with excellent catalytic performances in the reuses.

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Hollow Co@HCN Derived from ZIF-67 as a Highly Efficient Catalyst for Hydrogenation of o-Cresol to o-Methyl Cyclohexanol

et al. 2023

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Imprint of free space around acid site in hollow mesoporous polymeric solid acid and application in heterogeneous acetal hydrolysis/asymmetric aldol tandem reaction

Cited by 15 publications

References 57 publications

Porous Organic Polymer with Free Carboxylic Acids (Carboxy‐POP) for Heterogeneous Catalytic One‐Pot Synthesis of Xanthenes and Acridines

Porous Organic Polymer with Free Carboxylic Acids (Carboxy‐POP) for Heterogeneous Catalytic One‐Pot Synthesis of Xanthenes and Acridines

“Ship‐in‐a‐Bottle” Strategy for Immobilization of 9‐Amino(9‐deoxy)epi‐Cinchona Alkaloid into Molecularly Imprinted Solid Acid: Acetal Hydrolysis/Asymmetric Aldol Tandem Reaction

Hollow Co@HCN Derived from ZIF-67 as a Highly Efficient Catalyst for Hydrogenation of o-Cresol to o-Methyl Cyclohexanol

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