Ligand-free direct C-arylation of heterocycles with aryl halides over a metal-organic framework Cu2(BPDC)2(BPY) as an efficient and robust heterogeneous catalyst

Le, Hanh T.N.; Nguyen, Tung T.; Vu, Phuong H.L.; Truong, Thanh; Phan, Nam T. S.

doi:10.1016/j.molcata.2014.03.017

Cited by 33 publications

(6 citation statements)

References 58 publications

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“…Heterogeneous copper catalysts are recognized for their applications in oxidation, click chemistry, and Ullmann and Goldberg coupling reactions . Their use in C–H functionalization, however, is much less developed and comprehensive studies on the active catalytic species of copper-based systems have only recently started to be explored . For example, Corma and co-workers reported on the elucidation of clusters as active catalytic species in “homogeneous” copper-catalyzed cross-coupling reactions .…”

Section: Introductionmentioning

confidence: 99%

Direct C–H Arylation of Heteroarenes with Copper Impregnated on Magnetite as a Reusable Catalyst: Evidence for CuO Nanoparticle Catalysis in Solution

et al. 2016

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A reusable copper-based catalyst system was employed for the direct arylation of electron-rich heteroarenes. Under mild and operationally simple reaction conditions good yields and selectivities were obtained using diaryliodonium salts as coupling partners. A combination of experimental methods including kinetic studies, filtration tests, and a series of analytical tools (TXRF, ICP-MS, SEM, XPS, TEM, EFTEM) provide evidence for catalytically active soluble nanoparticles formed from an amorphous heterogeneous precursor. Mechanistic studies hint at a redox-neutral process which promotes counterion dissociation from the diaryliodonium salt by a copper(II) oxide species.

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Section: Introductionmentioning

confidence: 99%

Direct C–H Arylation of Heteroarenes with Copper Impregnated on Magnetite as a Reusable Catalyst: Evidence for CuO Nanoparticle Catalysis in Solution

et al. 2016

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“…The crystal structure of these types of MOFs reveals that dicarboxylates behave as grid-forming ligands and diamines or diimines acts as pillars, thus allowing the reactants to diffuse favorably to reach the active sites. In one of these examples, C–H arylation between benzoxazole and iodobenzene (Scheme ) was reported using Cu 2 (BPDC) 2 (BPY) as solid catalyst at 120 °C in DMSO and K 3 PO 4 as the base, reaching complete conversion and selectivity . Control experiments with homogeneous copper salts indicated that the yield of the reaction is comparatively superior with heterogeneous MOF catalyst than with homogeneous copper catalysts.…”

Section: C–c Bond Formationmentioning

confidence: 99%

Formation of C–C and C–Heteroatom Bonds by C–H Activation by Metal Organic Frameworks as Catalysts or Supports

2018

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Cross coupling reactions catalyzed by transition metals are currently among the most widely used transformations in organic synthesis. In most of these reactions, the coupling involves the reaction of two complementary functional groups, particularly boronates and halides. For the sake of atom economy and simplicity of the starting materials, it is more advantageous when the coupling involves C-H activation of one substrate lacking a reactive functional group. The present review focuses on the use of metal organic frameworks (MOFs) as solid reusable catalysts to promote cross-coupling reactions involving C-H activation. After general considerations, the review is organized according to the bond formed in the coupling, either CC or C-heteroatom (N, O, B and X). The purpose of this mini review is to show the performance of MOFs as heterogeneous catalysts in these reactions, combining a high activity due to the large percentage of accessible metal sites and high stability allowing the reuse of the material in consecutive cycles. Comparison with homogeneous analogous catalysts indicates that this improved performance derives from the porosity, large surface area and site isolation and immobilization occurring in the MOFs. Considering the growing interests in these reactions the last section forecasts future developments in these areas in near future.

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“…Aryl-substituted benzoxazoles, benzimidazoles, and benzothiazoles are also a valuable class of heterocyclic compounds that have a wide range of biological activities, including antitumor, antiviral, anti-inflammatory, antihypertensive, antihistaminic, and antimicrobial activities. − Two well-known methods for the preparation of these compounds have been developed: (i) metal-catalyzed direct alkylation of benzoxazoles, benzimidazoles, and benzothiazoles through C–H activation followed by C–C bond formation; − (ii) condensation–aromatization of o -aminophenol, o -phenylenediamine, and o -aminothiophenols with aldehydes using Brønsted or Lewis acid catalysts. − Although the reported methods are satisfactory, synthesis of these compounds remains challenging, with procedures suffering from low yields, additional additives or volatile organic solvents, and expensive and unrecyclable catalysts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Benzoxazoles, Benzimidazoles, and Benzothiazoles Using a Brønsted Acidic Ionic Liquid Gel as an Efficient Heterogeneous Catalyst under a Solvent-Free Condition

Nguyen

Tran

2019

ACS Omega

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Herein, we introduce a reusable Brønsted acidic ionic liquid gel (BAIL gel) obtained by treating 1-methyl-3-(4-sulfobutyl)-1 H -imidazolium hydrogen sulfate with tetraethyl orthosilicate (TEOS). The grafting of the Brønsted acidic ionic liquid to the surface of TEOS has increased the catalytic activity of the material and also simplified catalyst recovery from the reaction mixture. This reaction has a wide substrate scope, and the BAIL gel represents a new catalyst for the synthesis of benzoxazoles, benzimidazoles, and benzothiazoles. The method shows attractive characteristics such as high yields, recyclable catalyst, and work-up simplicity. More importantly, no additional additives or volatile organic solvent and inert atmosphere are required for the reaction, and the BAIL gel has shown a great promise for industrial applications. To the best of our knowledge, the synthesis of benzoxazoles, benzimidazoles, and benzothiazoles using a recyclable heterogeneous ionic liquid gel was not previously reported in the literature.

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Ligand-free direct C-arylation of heterocycles with aryl halides over a metal-organic framework Cu2(BPDC)2(BPY) as an efficient and robust heterogeneous catalyst

Cited by 33 publications

References 58 publications

Direct C–H Arylation of Heteroarenes with Copper Impregnated on Magnetite as a Reusable Catalyst: Evidence for CuO Nanoparticle Catalysis in Solution

Direct C–H Arylation of Heteroarenes with Copper Impregnated on Magnetite as a Reusable Catalyst: Evidence for CuO Nanoparticle Catalysis in Solution

Formation of C–C and C–Heteroatom Bonds by C–H Activation by Metal Organic Frameworks as Catalysts or Supports

Synthesis of Benzoxazoles, Benzimidazoles, and Benzothiazoles Using a Brønsted Acidic Ionic Liquid Gel as an Efficient Heterogeneous Catalyst under a Solvent-Free Condition

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