Microwave-assisted synthesis of ultrafine Au nanoparticles immobilized on MOF-199 in high loading as efficient catalysts for a three-component coupling reaction

Jiang, Yan; Zhang, Xin; Dai, Xiaoping; Zhang, Wen; Shen, Qiang; Zhuo, Hongying; Xiao, Yun; Wang, Hai

doi:10.1007/s12274-016-1341-1

Cited by 56 publications

(18 citation statements)

References 61 publications

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“…These significant differences make it difficult to compare the performance of resultant Au catalysts from different studies, even in the same catalytic reaction. For example, the three‐component coupling of aldehyde, amine, and alkyne (also called A 3 coupling) is a representative type of CH bond activation reaction to produce propargylamine and its derivatives, serving as an important intermediate for the synthesis of many nitrogen‐containing biological and pharmaceutical compounds, which can be catalyzed by Au 0 and Au δ + (δ > 0, representing the oxidation state of Au species) according to the previous reports . For example, Liu et al sythesized an Au/MIL‐53(Al) catalyst‐containing Au 0 and Au 3+ species, which display good activity for the A 3 coupling reaction .…”

Section: Methodsmentioning

confidence: 99%

Oxidation or Reduction State of Au Stabilized by an MOF: Active Site Identification for the Three‐Component Coupling Reaction

Yang

Jiang

2018

Small Methods

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and alkyne (also called A 3 coupling) is a representative type of CH bond activation reaction to produce propargylamine and its derivatives, serving as an important intermediate for the synthesis of many nitrogen-containing biological and pharmaceutical compounds, which can be catalyzed by Au 0 and Au δ+ (δ > 0, representing the oxidation state of Au species) according to the previous reports. [8][9][10][11][12] For example, Liu et al. sythesized an Au/MIL-53(Al) catalyst-containing Au 0 and Au 3+ species, which display good activity for the A 3 coupling reaction. [13] In addition, Liu et al. also demonstrated the Au 3+ -containing catalyst, IRMOF-3-LA-Au, can exhibit good performance in the A 3 coupling reaction. [14] Some comparative studies have been attempted, such as the contrastive properties of gold salts and Au 0 sponges, or the activity comparison between Au NPs/PMO (PMO = periodic mesoporous organosilica) and Au(PPh 3 )Cl. [15,16] Unfortunately, these comparisons have not been able to exactly give the intrinsic property of different Au species due to the presence of different supports, which is a potential factor to affect the activity. There is still an intensive debate on the nature of the gold species involved in the reaction after the elimination of the support effect. Therefore, it is necessary to seek for a suitable model with the only difference in Au oxidation state to identify the efficient active site.As a relatively new class of crystalline porous materials, metal-organic frameworks (MOFs), featuring high porosity, structural diversity, and tailorability are attracting extensive interest and are employed toward various applications including gas storage and separation, drug delivery, sensing, catalysis, etc. [17][18][19][20][21][22][23][24][25] MOFs exhibit an unrivalled ability to realize atom-level structural determination and tailoring. Particularly, some particular functional groups with strong chelating/anchor ability can be facilely grafted onto the MOF pore walls via either onestep assembly or postsynthetic modification (PSM). [26][27][28] This character makes MOFs might be ideal supports to stabilize Au 0 and Au δ+ for studying structure-catalytic activity relationship.With the above considerations in mind, we rationally introduced the salicylaldehyde (SA) and HAuCl 4 precursors into a mesoporous MOF, MIL-101-NH 2 , via a PSM approach. SA was bound to the MOF via the reaction with the amino group to give corresponding product (denoted as MIL-101-SA) with imine As one of the most efficient catalysts for the three-component coupling reaction of aldehyde, amine, and alkyne (A 3 coupling), Au has attracted extensive attention, but there is a debating issue on whether Au δ+ (δ > 0, representing the oxidation state of Au species) or Au 0 is the better active site. According to previous reports, both Au δ+ and Au 0 can catalyze the A 3 coupling reaction. Therefore, the establishment of a suitable comparison model to identify the better active site is highly desired. In this work, an ideal m...

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Section: Methodsmentioning

confidence: 99%

Oxidation or Reduction State of Au Stabilized by an MOF: Active Site Identification for the Three‐Component Coupling Reaction

Yang

Jiang

2018

Small Methods

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“…The VB potential for CuO (1.51 eV) is more positive than that of MB (1.17 eV); therefore, h + could easily oxidize MB to form degradation products (equation (14)). On the other hand, the CB edge position of CuO (−0.43 eV) is more negative than that of E 0 (O 2 /O 2 ⋅− ) (−0.33 eV) [51]; thus, electrons on the conduction band of CuO reacts with O 2 to produce superoxide radical O 2 ⋅ , which could substantially oxidize MB to form degradation products (equations (15) and (16)). In principle, h + (1.51 eV) could not oxidize H 2 O (EðH 2 O/ ⋅ OHÞ = 2:6 eV), but the experimental result still indicates the role of ⋅ OH in the oxygenation of dye as shown in Figure 12.…”

Section: Visible-light-driven Photocatalytic Degradation Of Mbmentioning

confidence: 99%

“…HKUST-1 (Hong Kong University of Science and Technology) is one of the first MOFs made up of copper nodes with benzene-1,3,5tricarboxylic (BTC) acid struts between them [13]. or Cu-BTC) manifests remarkable potentials in photocatalysis [14,15] and separation [16]. notably displays persistence in both water and air [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Porous Octahedral ZnO/CuO Composites from Zn/Cu-Based MOF-199 and Their Applications in Visible-Light-Driven Photocatalytic Degradation of Dyes

Minh

Thi

et al. 2019

Journal of Nanomaterials

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In the present paper, a porous octahedral (ZnO/CuO) composite is synthesized from zinc/copper-based metal-organic framework-199, and its applications in visible-light-driven photocatalytic degradation of dyes are demonstrated. The precursors of Zn-BTC, Cu-BTC, and Zn/Cu-BTC (BTC: benzene-1,3,5-tricarboxylate) were synthesized using a microwave-assisted method. Benzene-1,3,5-tricarboxylate acts as a sacrificial template and was removed from the precursors via thermal decomposition to form CuO, ZnO, and ZnO/CuO. ZnO/CuO with a large specific surface area of 32.5 m 2 ·g -1 is composed of porous octahedral particles of 5-10 μm in diameter. Methylene blue (MB) was utilized as the dye model for photocatalytic degradation reactions. The porous octahedral ZnO/CuO exhibits superior visible-light-driven photocatalytic degradation of MB compared with single CuO or ZnO. The kinetic model of photocatalytic degradation was proposed as ð1/K L Þ × ln C + C = −k r t + ð1/K L Þ × ln C e + C e , where K L is the Langmuir equilibrium constant and C e is the MB concentration at equilibrium. The model significantly fits the kinetic data. In addition, the acquired catalyst manifests excellent photocatalytic degradation for several other dyes including phenol red, methyl orange, and Congo red.

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“…[36] The multicomponent reaction of alkynes, aldehydes and amines, identified as A 3 -coupling, offers an effective, useful and atom-effective access to propargylamines [37] that are critical intermediates of natural and biological compounds such as oxazoles, [38] acrylamidines, [39] pyrrolidines, [40] and pyrrole. [41] Given this significance, various metal sources have been applied to promote this reaction including Au, [42,43] Ag, [44,45] Cu(I), [46] Rh (III), [47] or In (III) [48] that activate the alkyne and aldehyde C-H bonds. [37] More transition metals, such as Fe (III), [49] Zn (II) [50] and Ni (II) [50] have also been employed, howbeit under inert conditions with high catalyst loadings.…”

Section: Introductionmentioning

confidence: 99%

Porous triazine polymer: A novel catalyst for the three‐component reaction

Nouruzi

Dinari

Mokhtari

et al. 2020

Applied Organom Chemis

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A new porous triazine-based covalent organic polymer (Triazine-COP) was prepared through the Schiff-base condensation of 2,4,6-tris(4-formyl phenoxy)-1,3,5-triazine and 4,4 0-oxydianiline, under sonication. The synthesized Triazine-COP with a high surface area was stable in water and other organic solvents. In the next step, Au (III) ions were immobilized on the nitrogen-rich Triazine-COP that on the reduction with NaBH 4 produced the heterogeneous catalyst of gold clusters in nanosize (Au-NCs@Triazine-COPs). It was applied as an efficient catalyst for the A 3 coupling reaction of alkynes, aldehydes with and amines. Both electron-withdrawing/releasing groups produced the corresponding propargylamines with high yields. The high activity of the Au-NCs@Triazine-COPs in this reaction was because of the nanoporous structure of the support that enables the high dispersion and an unhindered open environment for the NCs. The catalyst was reused up to 7 times without significant loss in activity.

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Microwave-assisted synthesis of ultrafine Au nanoparticles immobilized on MOF-199 in high loading as efficient catalysts for a three-component coupling reaction

Cited by 56 publications

References 61 publications

Oxidation or Reduction State of Au Stabilized by an MOF: Active Site Identification for the Three‐Component Coupling Reaction

Oxidation or Reduction State of Au Stabilized by an MOF: Active Site Identification for the Three‐Component Coupling Reaction

Synthesis of Porous Octahedral ZnO/CuO Composites from Zn/Cu-Based MOF-199 and Their Applications in Visible-Light-Driven Photocatalytic Degradation of Dyes

Porous triazine polymer: A novel catalyst for the three‐component reaction

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