Cu3(BTC)2 as a viable heterogeneous solid catalyst for Friedel-Crafts alkylation of indoles with nitroalkenes

Anbu, Nagaraj; Dhakshinamoorthy, Amarajothi

doi:10.1016/j.jcis.2017.01.091

Cited by 35 publications

(15 citation statements)

References 35 publications

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“…One of the possible ways to overcome this issue is to develop heterogeneous catalysts to activate electrophilic β-nitrostyrene toward nucleophilic addition of indole through hydrogen bonding. This reaction has been previously exploited using a series of MOF catalysts, which include squaramide-functionalized UiO-67 MOF, NU-601, Cr-MIL-101-UR3, Cu-UBTA, Cu(dbda), [Zn 4 O(4,4′-ureylene-benzenedicarboxylate) (DMF) 2 ]·3DMF, and Cu 3 (BTC) 2 …”

Section: Resultsmentioning

confidence: 99%

“…This reaction has been previously exploited using a series of MOF catalysts, which include squaramide-functionalized UiO-67 MOF, 67 NU-601, 26 Cr-MIL-101-UR3, 58 Cu-UBTA, 54 Cu(dbda), 68 [Zn 4 O-(4,4′-ureylene-benzenedicarboxylate) (DMF) 2 ]•3DMF, 52 and Cu 3 (BTC) 2 . 69 Initially, the catalytic activity of 1′ was studied in the product are higher with 3.8 mol % catalyst than the other two loadings. Therefore, the optimization of this reaction with respect to temperature and solvent was performed using 3.8 mol % catalyst loading.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Highly Active Urea-Functionalized Zr(IV)-UiO-67 Metal–Organic Framework as Hydrogen Bonding Heterogeneous Catalyst for Friedel–Crafts Alkylation

Das

Anbu

et al. 2019

Inorg. Chem.

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A new Zr(IV)-based UiO-67 metal–organic framework (1) was prepared with urea-functionalized biphenyl-4,4′-dicarboxylic acid (BPDC-urea) as the linker using conventional solvothermal technique and thoroughly characterized using X-ray powder diffraction (XRPD), Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric (TG), and N2 sorption analyses. The activated form of 1 (called 1′) exhibited excellent BET surface area in spite of having a large functional moiety (urea) in the linker side. The activated form of this material (1′) was successfully employed for the Friedel–Crafts alkylation of indole with β-nitrostyrene to achieve 97% yield in toluene at 70 °C for 24 h. Furthermore, the catalyst was used for four cycles, with no significant loss in its activity, and the reaction was heterogeneous in nature. The activity of 1′ was comparable to UiO-67-(NH2)2, whereas the activity was 2-fold higher compared to the parent UiO-67. Further, the activity of the BPDC-urea linker was nearly 2-fold higher than that of ZrCl4, suggesting the crucial role played by the urea moiety than the metal node. In addition, the catalyst (1′) exhibited a wide substrate scope, allowing the preparation of a series of compounds with moderate to high yields under the optimized reaction conditions. The roles of metal salt and linker in the catalysis have also been studied separately, and the mechanism for the catalysis has been clarified.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Highly Active Urea-Functionalized Zr(IV)-UiO-67 Metal–Organic Framework as Hydrogen Bonding Heterogeneous Catalyst for Friedel–Crafts Alkylation

Das

Anbu

et al. 2019

Inorg. Chem.

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“…Dhakshinamoorthy et al suggested that Cu 3 (BTC) 2 was an active catalyst for the synthesis of borasiloxanes from silanes and pinacolboranes. Anbu and Dhakshinamoorthy described the activity of Cu 3 (BTC) 2 in the Friedel–Crafts alkylation of indole with β-nitrostyrene. Surprisingly, the stability of CuBTC did not seem to be an issue in either of these cases.…”

Section: Mofs With Intrinsic Catalytic Activitymentioning

confidence: 99%

Metal–Organic Frameworks in Heterogeneous Catalysis: Recent Progress, New Trends, and Future Perspectives

et al. 2020

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More than 95% (in volume) of all today's chemical products are manufactured through catalytic processes, making research into more efficient catalytic materials a thrilling and very dynamic research field. In this regard, Metal Organic Frameworks (MOFs) offer great opportunities for the rational design of new catalytic solids, as highlighted by the unprecedented number of publications appearing over the last decade. In this review, the recent advances in the application of MOFs in heterogeneous catalysis are discussed. MOFs with intrinsic thermo-catalytic activity, as hosts for the incorporation of metal nanoparticles, as precursors for the manufacture of composite catalysts and those active in photo and electrocatalytic processes are critically reviewed. The review is wrapped up with our personal view on future research directions.

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“…With CuO MOF Y A , the initial reaction rate increases 2-fold with respect to the pure Faujasite acid support and the TOF Cu is 2 orders of magnitude higher with respect to CuBTC: 104 vs 5 h –1 (see Figure S8 and Table S7). , Those findings indicate that the novel method of creating CuO active sites in acidic supports could be unique and generic for different catalytic reactions. To broaden the scope of this concept, we have also employed zinc MOFs as precursor of inexpensive and nontoxic ZnO acid–base sites on H-USY.…”

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confidence: 95%

Metal-Organic Framework Derived Metal Oxide Clusters in Porous Aluminosilicates: A Catalyst Design for the Synthesis of Bioactive aza-Heterocycles

et al. 2018

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Simple solid-state mixing and calcination of catalytic amounts of MOFs in the presence of aluminosilicates allows for the generation of active and robust supported metal oxide nanoparticles that catalyze C-C and C-N bond formations. The proposed Cu and Zn containing aluminosilicates outperform state-of-the-art solid catalysts for the synthesis of various azaheterocycles under mild and heterogeneous conditions, exhibiting the highest TOFs ever reported for cost-efficient and reusable CuO and ZnO active sites.

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Cu3(BTC)2 as a viable heterogeneous solid catalyst for Friedel-Crafts alkylation of indoles with nitroalkenes

Cited by 35 publications

References 35 publications

Highly Active Urea-Functionalized Zr(IV)-UiO-67 Metal–Organic Framework as Hydrogen Bonding Heterogeneous Catalyst for Friedel–Crafts Alkylation

Highly Active Urea-Functionalized Zr(IV)-UiO-67 Metal–Organic Framework as Hydrogen Bonding Heterogeneous Catalyst for Friedel–Crafts Alkylation

Metal–Organic Frameworks in Heterogeneous Catalysis: Recent Progress, New Trends, and Future Perspectives

Metal-Organic Framework Derived Metal Oxide Clusters in Porous Aluminosilicates: A Catalyst Design for the Synthesis of Bioactive aza-Heterocycles

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