Nickel/magnesium–lanthanum mixed oxide catalyst in the Kumada-coupling

Kiss, Árpád; Hell, Zoltán; Bálint, Mária

doi:10.1039/b919246h

Cited by 31 publications

(17 citation statements)

References 28 publications

(6 reference statements)

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“…Kiss et al immobilized Ni on various inorganic supports such as hydrotalcite, mixed MgLaO, and 4Å molecular sieves, and came to the conclusion that MgLaO, where the Ni was incorporated into the surface structure of the support, was the best support for the Kumada-Corriu catalyst. 82 The catalysts described in these examples exhibit different turnover numbers (TONs), extent of leaching, and catalytic efficiencies, but, in general, are of considerable scientific interest.…”

Section: Protection Of Catalytic Nanoparticles Against Agglomerationmentioning

confidence: 99%

“…Another class of supports, namely, mixed metal oxides, was explored by Kiss et al, who also tried combining different transition metals (such as Fe, Co, Ni, and Pd) with difference types of supports (such as hydrotalcite, mixed MgLaO, and 4Å molecular sieves) only to conclude that the Ni(II) precatalyst on MgLaO gave the best yields. 82 The catalyst itself was not a simple "Ni-on-oxide" species; the Ni exchanged, probably with magnesium, and was incorporated into the surface structure of the mixed oxide support. This is supported by the ICP optical emission spectroscopy results, which showed a slight decrease in the Mg : La ratio upon comparing the pure support and the catalyst.…”

Section: Kumada-corriu Couplingmentioning

confidence: 99%

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Nanocatalysts for Hiyama, Stille, Kumada, and Negishi C–C Coupling Reactions

Banerjee

Scott

2013

Nanocatalysis Synthesis and Applications

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INTRODUCTIONIn the last century, the synthetic organic chemist had formidable resources available for the design and preparation of new complex molecules. 1, 2 However, in the twenty-first century, it is essential for a successful synthetic strategy not only to yield new, pure products selectively but also to develop processes that are environmentally friendly, cost-effective, and dependent on renewable feedstocks rather than on fast-depleting fossil fuels or their derivatives. [3][4][5] The burgeoning field of catalytic nanomaterials, or nanocatalysts, offers an opportunity to the modern synthetic chemist to follow the tenets of green chemistry without compromising on crucial factors such as yield and selectivity of products. 6 Current emphasis on catalysis using nanomaterials, which straddles the boundaries of homogeneous and heterogeneous catalysis, often combining the benefits of both, underscores the quest for recyclable catalytic materials. 7 In this field of research, the formation of new C C bonds using nanomaterials has emerged as a challenging new problem that is being studied across the globe. 8 C C couplings are now a staple of modern organic chemistry, as evidenced by the recent Nobel Prize award in chemistry to Heck, Negishi, and Suzuki in 2010. A recent Web of Knowledge R search shows the almost exponential growth in the number of literature reports related to interdisciplinary research involving nanochemistry and organic synthesis during the past decade ( Figure 5.1).

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Section: Protection Of Catalytic Nanoparticles Against Agglomerationmentioning

confidence: 99%

Section: Kumada-corriu Couplingmentioning

confidence: 99%

Nanocatalysts for Hiyama, Stille, Kumada, and Negishi C–C Coupling Reactions

Banerjee

Scott

2013

Nanocatalysis Synthesis and Applications

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“…6). The catalysts were prepared by the impregnation of the support with the appropriate metal salt [14].…”

Section: The Kumada-couplingmentioning

confidence: 99%

Supported Metal Catalysts in Organic Syntheses

Kiss

Nemeth

Fodor

et al. 2015

Period. Polytech. Chem. Eng.

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The importance of heterogeneous catalytic methods in organic syntheses is growing dynamically. Among the methods developed the supported metal catalysts take up an outstanding role. In this paper the results of the research group obtained in this field are reviewed. Keywords heterogeneous catalysis, supported metal catalysts, organic syntheses IntroductionMost organic syntheses require a catalyst for good conversion. With the exception of heterogeneous oxidation and reduction, these catalysts are mostly acids or bases. The traditional acids and bases have several disadvantageous properties, they are often dangerous, flammable, corrosive, or toxic, the workup of the reaction mixture is often tedious, producing high amounts of waste water, and the catalyst often decomposes during the workup procedure. These compounds or even their preparation is often harmful for the environment. Therefore in recent decades the development of heterogeneous catalytic methods became one of the main synthetic goals. The heterogeneous catalysts can eliminate the problems arising from the use of a homogeneous catalyst; they can be filtered out from the reaction mixture, simplifying this way the workup procedure, reducing the energy costs and decreasing the operation time as well as the amount of waste water. They are generally non-corrosive, non-toxic and often reusable or simply recyclable materials, and in some cases they can induce a considerable regio-even stereoselectivity. There were several minerals found in nature which showed excellent catalytic avtivity in organic syntheses. Based on these materials numerous mineralbased heterogeneous catalysts were developed in recent years not only for laboratory but also for industrial use. Thus, e.g. in a review published in 1999 about the heterogeneous catalytic industrial processes, 71 methods were presented which used natural, modified or artificial zeolites [1].These materials can also serve as supports of different metals. The acidic or basic properties of the support, their great surface as well as the fine dispersity of the metal on the support's surface can significantly increase the efficiency of these catalysts. Furthermore, the ligands which are often required for a homogeneous catalytic process, can be omitted in the heterogeneous methods, which can increase the atom efficiency of the process and make the workup of the reaction mixture easier.

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“…Acoplamento de Kumada com catalisador heterogêneo 43 Hell e colaboradores 45 testaram catalisadores de diferentes metais de transição em suportes básicos no acoplamento de Kumada entre o brometo de fenilmagnésio e o bromobenzeno. Como suportes, foram testados: hidrotalcita (HT) (Mg : Al = 2 : 1 ou 3 : 1), óxido misto de magnésio e lantânio (MgLaO; Mg : La = 3 : 1), óxido de lantânio, óxido de magnésio e peneira molecular (Ni (II)-4A).…”

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“…Como suportes, foram testados: hidrotalcita (HT) (Mg : Al = 2 : 1 ou 3 : 1), óxido misto de magnésio e lantânio (MgLaO; Mg : La = 3 : 1), óxido de lantânio, óxido de magnésio e peneira molecular (Ni (II)-4A). Alguns dos resultados obtidos por Hell e colaboradores 45 estão reproduzidos na Tabela 7.…”

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Kumada-Corriu-Tamao couplings catalyzed by Ni and Pd as an important tool for the biaryl synthesis

Martins¹

2010

Revista Virtual De Química

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Abstract:Cross-coupling reactions catalyzed by transition metal complexes are important tools in the synthesis of biaryls, building blocks in a variety of compounds with interesting applications. The contributions of the palladium-catalyzed cross-coupling reactions to organic synthesis were recognized in 2010 when R. F. Heck, E. Negishi and A. Suzuki were awarded the Nobel Prize in Chemistry. Biarylic systems are usually obtained by a C(sp 2 )-C(sp 2 ) bond formation process catalyzed by Ni or Pd and several methodologies are currently available for their synthesis, for example, the Suzuki reaction, or Stille, Hiyama, Negishi, or Kumada-Corriu-Tamao crosscoupling. In this work, the Kumada-Corriu-Tamao methodology is investigated. The main characteristics of the reaction, like the catalytic systems employed, the different classes of substrates, and the optimization of the experimental protocol will be discussed as well. Application of this methodology in the synthesis of molecules of interest will also be addressed. The Kumada-Corriu-Tamao methodology is claimed to be the precursor of all other cross-coupling methodologies, pushing the frontiers of the organic synthesis.Keywords: biaryls; C-C coupling; Kumada-Corriu-Tamao; niquel; palladium; Nobel 2010. ResumoOs acoplamentos cruzados catalisados por metais de transição são ferramentas muito importantes na construção de sistemas biarílicos, os quais estão presentes na estrutura de diversas substâncias com aplicações importantes na terapêutica médica e na indústria química. A importância dos acoplamentos cruzados foi reconhecida pela concessão do prêmio Nobel de 2010 aos pesquisadores R. F. Heck, E. Negishi e A. Suzuki. Geralmente, os sistemas biarílicos são obtidos mediante a formação de ligações C(sp 2 )-C(sp 2 ) entre dois anéis aromáticos através de um processo catalisado por Ni ou Pd. Várias metodologias de acoplamento estão disponíveis para o preparo de biarilas como, por exemplo, as reações de Suzuki, Stille, Hiyama, Negishi ou Kumada-Corriu-Tamao. Neste trabalho, será abordado o acoplamento de Kumada-Corriu-Tamao: as características principais, os sistemas catalíticos empregados, os diferentes substratos e o processo de desenvolvimento da metodologia que alavancou os acoplamentos cruzados conhecidos e largamente empregados atualmente.

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Nickel/magnesium–lanthanum mixed oxide catalyst in the Kumada-coupling

Abstract: A new, heterogeneous, magnesium-lanthanum mixed oxide solid base-supported nickel(ii) catalyst was developed. The catalyst was used successfully in the Kumada coupling of aryl halides, especially aryl bromides. The optimal reaction conditions of the coupling were determined.

Cited by 31 publications

References 28 publications

Nanocatalysts for Hiyama, Stille, Kumada, and Negishi C–C Coupling Reactions

Nanocatalysts for Hiyama, Stille, Kumada, and Negishi C–C Coupling Reactions

Supported Metal Catalysts in Organic Syntheses

Kumada-Corriu-Tamao couplings catalyzed by Ni and Pd as an important tool for the biaryl synthesis

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