C-C Coupling Reactions in Water Catalyzed by Palladium

Kong, Shuang; Malik, Abaid Ullah; Qian, Xuefeng; Shu, Mouhai; Xiao, Wen‐De

doi:10.6023/cjoc201709016

Cited by 7 publications

(1 citation statement)

References 45 publications

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“…This synthesis approach has revolutionized the production of advanced materials [15,16,17,18], pharmaceuticals [19,20,21], agrochemicals [21,22], liquid crystals [23], and natural or biologically active compounds [24,25,26,27,28], etc. Numerous attractive strategies have been developed to address the ample scope of this catalytic process including the utilization of palladium nanoparticles [29,30,31,32,33,34,35], or palladium immobilized on magnetic nanoparticles [36] and natural supports [37], use of nucleophilic carbene ligands (mostly NHCs) [38,39,40,41,42,43,44,45,46], Schiff bases [47,48], water-soluble ligands like poly(ethylene glycol)-functionalized N-heterocyclic carbenes [49], thiourea [50] or phosphines [51,52], induction by microwave (MW) acceleration [53,54], use of “greener” solvents, such as water [55,56,57,58,59,60,61,62,63,64,65] (activated by MW [66,67] or in catalysis under micellar conditions [68] for enhancing the solubility of the aromatic halide), water–DMF […”

Section: Introductionmentioning

confidence: 99%

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

Ding

Yan

et al. 2018

Molecules

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An easy access to a series of previously unreported heterodinuclear Pd-Ln compounds, Pd-bpydc-La, Pd-bpydc-Ce and Pd-bpydc-Nd (bpydc = 2,2′-bipyridine-5,5′-dicarboxylate) has been developed. The Pd-Ln hybrid networks were effectively applied as catalysts in Suzuki–Miyaura C-C cross-coupling reactions of 4-bromoanisole and 4-bromobenzonitrile with phenylboronic acid, under mild conditions. A systematic investigation revealed Pd-bpydc-Nd as the most active catalyst. In all cases, reaction yields varied with the base, catalyst loading and substantially augmented with temperature (from 30 to 60 °C). Substituent effects were operative when changing from 4-bromoanisole to 4-bromobenzonitrile. The key role played by the lanthanides, aromatic substrate and base, in modulating the Pd-catalytic cycle has been highlighted. Importantly, the new catalysts proved to be stable in air and vs. functionalities and are quite efficient in Suzuki–Miyaura carbon-carbon bond formation conducted in protic solvents.

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Section: Introductionmentioning

confidence: 99%

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

Ding

Yan

et al. 2018

Molecules

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Synthesis of Enaminone‐Pd(II) Complexes and Their Application in Catalysing Aqueous Suzuki‐Miyaura Cross Coupling Reaction

Cao

Wan

et al. 2020

Chin. J. Chem.

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Summary of main observation and conclusion A series of Pd(II)‐enaminone complexes, termed Pd(eao)2, have been synthesized and characterized. The investigation on the catalytic activities of these new Pd(II)‐reagents has proved that the Pd(eao)2‐1 possesses excellent catalytic activity for the Suzuki‐ Miyaura cross coupling reactions of aryl bromides/chlorides with aryl/vinyl boronic acids in the environmentally benign media of aqueous PEG400 at low loading (5 mol‰). The superiority of this Pd(II)‐reagent to those commercial Pd(II) and Pd(0) catalysts in catalyzing the reactions has been confirmed by parallel experiments. What's more, Pd(eao)2‐2 has been found as a practical catalyst for the homo‐coupling reactions of aryl boronic acids.

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Highly Efficient and Reusable Polymer Supported Palladium Catalyst for Copper Free Sonogashira Reaction in Water

Sruthi

Nimmi²,

Babu

et al. 2022

ChemistrySelect

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Development of a novel, greener and efficient heterogeneous catalytic system for copper free Sonogashira reaction in water is described. This novel catalyst can be easily prepared by a simple method through synthetic modification of nitrile group in Polyacrylonitrile (PAN) using monoethanolamine (MEA) followed by its complexation with palladium chloride (PdCl2). The resulting polymer Pd complex (mPAN‐Pd) was characterized by means of Fourier Transform Infrared Spectroscopy (FTIR), Energy‐Dispersive X‐ray Spectroscopy (EDAX), Inductively Coupled Mass Spectrometry (ICP‐MS) and X‐ray Photo Electron Spectroscopy (XPS) analyses. mPAN‐Pd was then explored as highly efficient heterogeneous catalyst for Sonogashira coupling reaction under copper and ligand free conditions in water affording the corresponding coupling products up to 97 % isolated yield. Moreover, the catalyst was recovered by simple filtration after the reaction and reused for next 5 cycles with excellent stability and activity. This is the first report on the use of ethanolamine modified PAN Pd (II) complex as an efficient heterogeneous catalyst for a coupling reaction.

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C-C Coupling Reactions in Water Catalyzed by Palladium

Cited by 7 publications

References 45 publications

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

Synthesis of Enaminone‐Pd(II) Complexes and Their Application in Catalysing Aqueous Suzuki‐Miyaura Cross Coupling Reaction

Highly Efficient and Reusable Polymer Supported Palladium Catalyst for Copper Free Sonogashira Reaction in Water

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