Use of Nanoparticles as Catalysts in Organic Synthesis – Cross-coupling Reactions
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The review summarizes the use of metal nanoparticles as catalysts in cross-coupling reactions. Nanoparticle-sized catalysts are used in a variety of reactions, however, this chapter will focus on their use in the following cross-coupling reactions: Suzuki-Miyaura, Mizoroki-Heck, Sonogashira, Ullmann and Stille. Catalysts in nanoparticle size are often supported on other materials, referred to as catalyst supports. The various catalyst supports utilized for nanoparticles used in cross-coupling reactions will also be presented. Keywords: Nanoparticles, catalysis, palladium, copper, cross-coupling reactions, Suzuki-Miyaura reaction, Mizoroki-Heck reaction, Sonogashira reaction, Ullmann reaction, Stille reaction.Keywords:
Stille reaction
Sonogashira coupling
Coupling reaction
Organic Synthesis
Organic reaction
Practical approaches to multifunctional compounds through palladium on activated carbon, (Pd/C) -catalyzed Heck, Suzuki and Miyaura, Sonogashira, Fukuyama coupling and others are discussed. Correlation of the properties of the heterogeneous catalysts, e.g., palladium distribution and reduction degree, with the efficiency of the reaction has been observed and largely depends upon the type of the reactions. A critical role of the solid support is supposed to help palladium highly disperse on the solid surface to form active Pd complex without aggregating to inactive palladium black. The reactions are so practical as to be applied to cost-effective large-scale production of multifunctional intermediates for drug-synthesis.
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Palladium-catalyzed cross-coupling reactions have gained a continuously growing interest of synthetic organic chemists. The present review gives a brief account of applications of the palladium-catalyzed cross-coupling reactions in comprehensive synthesis, viz., the Heck, Stille, Suzuki-Miyaura, Negishi, Sonogashira, Buchwald-Hartwig, Ullmann and the Oxidative, decarboxylative cross-coupling reactions, with particular emphasis on the synthesis of heterocyclic compounds.
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Negishi coupling
Sonogashira coupling
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In this Special Issue, recent advances in cross-coupling reactions are presented in the form of original research articles, reviews, and short communications. These contributions cover different topics in this area, including novel coupling reactions, reaction conditions, synthetic alternatives, metal ligands, and applications for new pharmaceutical compounds and organic materials. In particular, the reviews deal with methodologies such as the synthesis of diarylketones through palladium catalysis and the most relevant examples of Suzuki–Miyaura and Buchwald–Hartwig coupling reactions in the synthesis of bioactive compounds. The synthetic utility of cross-coupling reactions for the synthesis of medium-size rings and the utility of Stille and Suzuki coupling reactions for the synthesis of new molecular machines based on sterically hindered anthracenyl trypticenyl units are also summarized. The original research articles present the synthesis of 2-alkynylpyrrols by inverse Sonogashira coupling and the synthesis of indoles under oxidative dearomative cross-dehydrogenative conditions. The efficient combination of iridium-catalyzed C–H borylation of aryl halides with the Sonogashira coupling and a sequential iridium-catalyzed borylation of NH-free pyrroles followed by a Suzuki–Miyaura reaction are included. The synthesis of aryl propionic acids, a common structural motif in medicinal chemistry, and the synthesis of new organic dyes are also covered.
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Borylation
Stille reaction
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Carbon–carbon and carbon–heteroatom coupling reactions are among the most important transformations in organic synthesis as they enable complex structures to be formed from readily available compounds under different routes and conditions. Several metal-catalyzed cross-coupling reactions have been developed creating many efficient methods accessible for the direct formation of new bonds between differently hybridized carbon atoms. During the last decade, much effort has been devoted towards improvement of the sustainability of these reactions, such as catalyst recovery and atom efficiency. Polyethylene glycol (PEG) can be used as a medium, as solid-liquid phase transfer catalyst, or even as a polymer support. PEG has been investigated in a wide variety of cross-coupling reactions either as an alternative solvent to the common organic solvents or as a support for catalyst, substrate, and ligand. In this review we will summarize the different roles of PEG in palladium- and copper-catalyzed cross-coupling reactions, with the focus on Heck, Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Stille, Fukuyama, and homocoupling reactions. We will highlight the role of PEG, the preparation of PEGylated catalysts and substrates, and the importance for the reaction outcome and applicability. 1 Introduction 2 PEG in Heck Reactions 3 PEG in Homocoupling Reactions 4 PEG in Suzuki–Miyaura Reactions 5 PEG in Sonogashira Reactions 6 PEG in Buchwald–Hartwig Reactions 7 PEG in Stille Reactions 8 PEG in Fukuyama Reactions 9 PEG in Miscellaneous Cross-Coupling Routes 10 Conclusions
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Stille reaction
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Negishi coupling
Stille reaction
Coupling reaction
Organic Synthesis
Heck Reaction
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A brief summary of selected pioneering and mechanistic contributions in the field of carbon-carbon cross-coupling reactions with palladium nanoparticles (Pd-NPs) in ionic liquids (ILs) is presented. Five exemplary model systems using the Pd-NPs/ILs approach are presented: Heck, Suzuki, Stille, Sonogashira and Ullmann reactions which all have in common the use of ionic liquids as reaction media and the use of palladium nanoparticles as reservoir for the catalytically active palladium species.
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Stille reaction
Coupling reaction
Carbon fibers
Heck Reaction
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Metal complexes play a vital role in inorganic and organic transformations. Schiff base (SB) and their metal complexes have emerged as versatile catalysts for numerous synthetic organic transformations. This chapter describes the numerous catalytic applications of SBs metal complexes for organic transformation. In recent years, the SB ligands and their metal complexes are employed as efficient catalysts for cross-coupling reactions such as Suzuki–Miyaura, Heck, Sonogashira, Buchwald–Hardwig, Negishi, Stile, and Kumada reactions in modern organic synthesis to generate C—C, C—N, C—O, and C—S bonds. The metal complex of SBs has been employed as an efficient catalyst for various types of polymerization reactions. Oxidation reaction is one of the most important reactions in organic synthesis and without this reaction, life would not exist.
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Negishi coupling
Organic Synthesis
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Palladium (Pd)-mediated cross-coupling reactions have been applied with great success to the synthesis of a wide variety of macrocyclic structures: they have found long-standing use in the construction of macrocyclic natural products and shape-persistent macrocycles (SPMs). They are also increasingly being used in medicinally oriented research, for example, in the synthesis of macrocyclic peptides. This chapter provides the diverse application of Pd-mediated cross-coupling, as well as related processes, in the synthesis of macrocyclic natural products and nonnatural macrocyclic derivatives. Classical cross-coupling processes, including Heck, Stille, Suzuki-Miyaura, and Sonogashira reactions, have been widely applied. The chapter also presents the examples to highlight some of the key strengths and weaknesses of Pd-catalyzed methods to perform the key macrocyclization step. It further deals with miscellaneous Pd-catalyzed macrocyclization reactions, which leads to the conclusions and a discussion of the future directions of this field.
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Synthesis of halotriazoles has been studied in the past few decades. Today, coupling reactions such as Heck, Suzuki, Sonogashira, and Stille are important tools in organic synthesis for the construction of C–C bonds. While these coupling reactions have been well utilized with simple haloarenes or halo‐olefins, now they are fast emerging on halotriazoles as well. This review summarizes the development of coupling reactions on halotriazoles, some of which are also biological relevant.
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Palladium represents one of the most exploited catalysts in organic synthesis, mainly applied in versatile methods for the formation of C-C bonds, but also in selective double bonds hydrogenation and oxidation processes, founding numerous industrial applications in particular in fine chemicals production. In the last decade, the use of metallic nanoparticles in catalysis has exploded (ca. 5,200 contributions in the period 2000-March 2010) and specifically ca. 40% of the reported works corresponds to palladium applications. Despite this widespread synthetic use of palladium nanoparticles (PdNP), less than 200 contributions analyse the mechanism of the catalyzed process taking into account the involvement of PdNP. The present review deals with the applications of PdNP in organic synthesis, starting from well-defined materials as catalytic precursors which represent less than 400 reported contributions. The discussion is organized by the type of organic transformation, mainly focused on C-X bond formation, hydrogenation and oxidation reactions. Keywords: Catalysis, C-C bond formation, Coupling, Enantioselective, Hydrogenation, Nanoparticles, Palladium, Oxidation, Cross-Coupling Reactions, Suzuki-Miyaura Reaction, Sonogashira-Hagihara Reaction, Stille Reaction, Hiyama Reaction, Homo-Coupling Reactions
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Sonogashira coupling
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