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Scope And Mechanistic Studies Of The Palladium On Carbon Catalyzed Suzuki Cross Coupling Reaction
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Book Synopsis Scope and Mechanistic Studies of the Palladium on Carbon Catalyzed Suzuki Cross Coupling Reaction by : Carl LeBlond
Download or read book Scope and Mechanistic Studies of the Palladium on Carbon Catalyzed Suzuki Cross Coupling Reaction written by Carl LeBlond and published by . This book was released on 2001 with total page 164 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Applied Cross-Coupling Reactions by : Yasushi Nishihara
Download or read book Applied Cross-Coupling Reactions written by Yasushi Nishihara and published by Springer Science & Business Media. This book was released on 2012-12-14 with total page 247 pages. Available in PDF, EPUB and Kindle. Book excerpt: “Applied Cross-Coupling Reactions” provides students and teachers of advanced organic chemistry with an overview of the history, mechanisms and applications of cross-coupling reactions. Since the discovery of the transition-metal-catalyzed cross-coupling reactions in 1972, numerous synthetic uses and industrial applications have been developed. The mechanistic studies of the cross-coupling reactions have disclosed that three fundamental reactions: oxidative addition, transmetalation, and reductive elimination, are involved in a catalytic cycle. Cross-coupling reactions have allowed us to produce a variety of compounds for industrial purposes, such as natural products, pharmaceuticals, liquid crystals and conjugate polymers for use in electronic devices. Indeed, the Nobel Prize for Chemistry in 2010 was awarded for work on cross-coupling reactions. In this book, the recent trends in cross-coupling reactions are also introduced from the point of view of synthesis design and catalytic activities of transition-metal catalysts.
Book Synopsis Mechanistic Studies on Palladium-catalyzed C-N Cross-coupling Reaction by : Pedro Luis Arrechea
Download or read book Mechanistic Studies on Palladium-catalyzed C-N Cross-coupling Reaction written by Pedro Luis Arrechea and published by . This book was released on 2016 with total page 253 pages. Available in PDF, EPUB and Kindle. Book excerpt: Mechanistic studies on the palladium catalyzed C-N bond-forming reaction were carried out to generate a more complete understanding of the catalytic cycle. To understand this reaction, several kinetic studies employing simple aryl halide and amine coupling partners were performed to elucidate unknown reaction pathways. Chapter 1. The resting state for the palladium catalyzed cross-coupling of various diarylamines and aryl halides is found to be the diphenylamido complex. Kinetic studies of the catalytic reaction are used to generate an Eyring plot. Hammett studies were performed for both the aryl halide and diarylamine coupling partners. The rates of reductive elimination for catalysts based on the biaryl ligands XPhos, CyJohnPhos, CPhos, BrettPhos, RuPhos, and SPhos were evaluated. Analogues of SPhos demonstrated that electron-donation of the lower aryl group is key to the stability of the amido complex in accordance with theoretical calculations. The methoxy substituent at the C3 position is demonstrated to retard the overall rate of reductive elimination for a RuPhos-BrettPhos hybrid ligand. These studies demonstrate that reductive elimination is likely not a problematic step for C-N cross-couplings. Chapter 2. Kinetic experiments demonstrated an inverse dependence on the concentration of both amine and aryl halide coupling partners. These observations are demonstrated to be valid for several amine classes, aryl halides, and biaryl ligands. Some work is done to demonstrate mechanistic overlap with other bidentate ligands. Based on these studies, a simplified reaction network for oxidative addition is proposed which reproduces key features of the experimental system.
Book Synopsis Palladium-Catalyzed Coupling Reactions by : Árpád Molnár
Download or read book Palladium-Catalyzed Coupling Reactions written by Árpád Molnár and published by John Wiley & Sons. This book was released on 2013-02-14 with total page 531 pages. Available in PDF, EPUB and Kindle. Book excerpt: This handbook and ready reference brings together all significant issues of practical importance in selected topics discussing recent significant achievements for interested readers in one single volume. While covering homogeneous and heterogeneous catalysis, the text is unique in focusing on such important aspects as using different reaction media, microwave techniques or catalyst recycling. It also provides a comprehensive treatment of key issues of modern-day coupling reactions having emerged and matured in recent years and emphasizes those topics that show potential for future development, such as continuous flow systems, water as a reaction medium, and catalyst immobilization, among others. With its inclusion of large-scale applications in the pharmaceutical industry, this will equally be of great interest to industrial chemists. From the contents * Palladium-Catalyzed Cross-Coupling Reactions - A General Introduction * High-turnover Heterogeneous Palladium Catalysts in Coupling Reactions: the Case of Pd Loaded on Dealuminated Y Zeolites Palladium-Catalyzed Coupling Reactions with Magnetically Separable Nanocatalysts * The Use of Ordered Porous Solids as Support Materials in Palladium-Catalyzed Cross-Coupling Reactions * Coupling Reactions Induced by Polymer-Supported Catalysts * Coupling Reactions in Ionic Liquids * Cross-Coupling Reactions in Aqueous Media * Microwave-Assisted Synthesis in C-C and C-Heteroatom Coupling Reactions * Catalyst Recycling in Palladium-Catalyzed Carbon-Carbon Coupling Reactions * Nature of the True Catalytic Species in Carbon-Carbon Coupling Reactions with * Heterogeneous Palladium Precatalysts * Coupling Reactions in Continuous Flow Systems * Large-Scale Applications of Palladium-Catalyzed Couplings in the Pharmaceutical Industry
Book Synopsis Synthetic Methods for Conjugated Polymer and Carbon Materials by : Mario Leclerc
Download or read book Synthetic Methods for Conjugated Polymer and Carbon Materials written by Mario Leclerc and published by John Wiley & Sons. This book was released on 2017-04-10 with total page 312 pages. Available in PDF, EPUB and Kindle. Book excerpt: A concise and practical overview of the most important modern synthetic aspects of conjugated polymers and carbon materials, including their properties and applications. Well structured, this book summarizes recent achievements, outlines the current state and reviews research trends. As such, a wide variety of polymerization techniques are included on both a strategic as well as a practical level, including Stille, Suzuki , and direct (hetero)arylation polymerizations. Furthermore, it covers various carbon-rich materials, such as graphene and carbon nanotubes, followed by a look at how the different synthetic pathways and strategies influence their final properties, for example, for use in organic electronic devices. The whole is rounded off with a discussion of future technology advances. An essential reference for newcomers as well as experienced researchers in the field.
Book Synopsis Cross-Coupling Reactions by : Norio Miyaura
Download or read book Cross-Coupling Reactions written by Norio Miyaura and published by Springer. This book was released on 2003-07-01 with total page 253 pages. Available in PDF, EPUB and Kindle. Book excerpt: In 1972, a very powerful catalytic cycle for carbon-carbon bond formation was 2 first discovered by the coupling reaction of Grignard reagents at the sp -carbon. Over the past 30 years, the protocol has been substantially improved and expanded to other coupling reactions of Li,B,N,O,Al,Si,P,S,Cu,Mn,Zn,In,Sn, and Hg compounds. These reactions provided an indispensable and simple methodology for preparative organic chemists. Due to the simplicity and rel- bility in the carbon-carbon, carbon-heteroatom, and carbon-metalloid bo- formations,as well as high efficiency of the catalytic process,the reactions have been widely employed by organic chemists in various fields. Application of the protocol ranges from various syntheses of complex natural products to the preparation of biologically relevant molecules including drugs, and of sup- molecules, and to functional materials. The reactions on solid surfaces allow robot synthesis and combinatorial synthesis. Now, many organic chemists do not hesitate to use transition metal complexes for the transformation of org- ic molecules. Indeed, innumerable organic syntheses have been realized by the catalyzed reactions of transition metal complexes that are not achievable by t- ditional synthetic methods. Among these, the metal-catalyzed cross-coupling reactions have undoubtedly contributed greatly to the development of such a new area of “metal-catalyzed organic syntheses”. An excellent monograph for the cross-coupling reactions and other met- catalyzed C-C bond-forming reactions recently appeared in Metal-catalyzed Cross-coupling Reactions (Wiley-VCH,1998).
Book Synopsis Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides by : Anant R. Kapdi
Download or read book Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides written by Anant R. Kapdi and published by Elsevier. This book was released on 2018-06-04 with total page 360 pages. Available in PDF, EPUB and Kindle. Book excerpt: Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides describes the procedures and protocols related to the modification of nucleosides, nucleotides and oligonucleotides via Pd-mediated cross-coupling processes. The book highlights the growing area of nucleic acid modification and how Pd-mediated coupling reactions can assist this development. Users will find key synthetic protocols for these reactions in this latest volume in the Latest Trends in Palladium Chemistry series. As most of the research in the field of antiviral agents has centered on the use of modified nucleosides that have exhibited promising activity, this book provides an up-to-date reference for both professionals in industry and other interested parties. Provides synthetic routes for useful nucleoside molecules, information otherwise found only through time-consuming literature searches Covers metal-mediated and metal-catalyzed cross coupling processes of nucleosides and related compounds Includes Suzuki-Miyaura, Stille and Sonogashira reactions, as well as C-H bond functionalization Highlights the growing area of nucleic acid modification and how Pd-mediated coupling reactions can assist
Book Synopsis Synthesis of Biaryls by : Ivica Cepanec
Download or read book Synthesis of Biaryls written by Ivica Cepanec and published by Elsevier. This book was released on 2010-07-07 with total page 365 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organic chemistry is one of the most rapidly growing sciences. There is a wide variety of applications of organic compounds, for instance, pharmaceutically active substances, agrochemicals, optoelectronics, etc. Within this group there are hundereds and thousands of new compounds synthesized or isolated from natural sources. Such important organic chemistry developments are accompanied by the profound break-through of new reactions, increasingly efficient methodologies, reagents and catalysts. The chemistry of biaryls is one of the most interesting fields in organic chemistry, this book looks at these reactions both new and old. Synthesis of Biaryls presents the description of a given method for the synthesis of biaryls: short introduction, reaction mechanism, application, representative synthetic procedures, conclusion and literature references. This book will be of interest to organic chemists in industry and academia. A topic of growing importance in organic synthesis The FIRST book to cover all reactions for the synthesis of biaryls, including the most recent The book provides detailed applications of each method described
Book Synopsis Palladium- and Nickel-catalyzed C-N Cross-coupling Reactions Featuring Soluble Organic Bases by : Joseph Michael Dennis (Jr.)
Download or read book Palladium- and Nickel-catalyzed C-N Cross-coupling Reactions Featuring Soluble Organic Bases written by Joseph Michael Dennis (Jr.) and published by . This book was released on 2020 with total page 549 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter 1: Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling Due to the low intrinsic acidity of amines, palladium-catalyzed C-N cross-coupling plagued continuously by the necessity to employ strong, inorganic, or insoluble bases. To surmount the many Due to the low intrinsic acidity of amines, palladium-catalyzed C-N crosscoupling has been practical obstacles associated with these reagents, we utilized a commercially available dialkyl triarylmonophosphine-supported palladium catalyst that facilitates a broad range of C-N coupling reactions in the presence of weak, soluble bases. The mild and general reaction conditions show extraordinary tolerance for even highly base-sensitive functional groups. Additionally, insightful heteronuclear NMR studies using −15N-labeled amine complexes provide evidence for the key acidifying effect of the cationic palladium center. Chapter 2: Pd-Catalyzed C-N Coupling Reactions Facilitated by Organic Bases: Mechanistic Investigation Leads to Enhanced Reactivity in the Arylation of Weakly Binding Amines The ability to use soluble organic amine bases in Pd-catalyzed C-N cross-coupling reactions has provided a long-awaited solution to the many issues associated with employing traditional, heterogeneous reaction conditions. However, little is known about the precise function of these bases in the catalytic cycle or about the effect of variations in base structure on catalyst reactivity. We used 19F NMR to analyze the kinetic behavior of C-N coupling reactions facilitated by different organic bases. In the case of aniline coupling reactions employing DBU, the resting state was a DBU-bound oxidative addition complex, LPd(DBU)(Ar)X, and the reaction was found to be inhibited by base. Generally, however, depending on the binding properties of the chosen organic base, increasing the concentration of the base can have a positive or negative influence on the reaction rate. Furthermore, the electronic nature of the aryl triflate employed in the reaction directly affects the reaction rate. The fastest reaction rates were observed with electronically neutral aryl triflates, while the slowest were observed with highly electron-rich and electrondeficient substrates. We propose a model in which the turnover-limiting step of the catalytic cycle is dependent on the relative nucleophilicity of the base, compared to that of the amine. This hypothesis guided the discovery of new reaction conditions for the coupling of weakly binding amines, including secondary aryl amines, which were unreactive nucleophiles in our original protocol. Chapter 3: Use of a Droplet Platform to Optimize Pd-Catalyzed C-N Coupling Reactions Promoted by Organic Bases Recent advances in Pd-catalyzed carbon-nitrogen cross-coupling have enabled the use of soluble organic bases instead of insoluble or strong inorganic bases that are traditionally employed. The single-phase nature of these reaction conditions facilitates their implementation in continuous flow systems, high-throughput optimization platforms, and large-scale applications. In this work, we utilized an automated microfluidic optimization platform to determine optimal reaction conditions for the couplings of an aryl triflate with four types of commonly employed amine nucleophiles: anilines, amides, primary aliphatic amines, and secondary aliphatic amines. By analyzing trends in catalyst reactivity across different reaction temperatures, base strengths, and base concentrations, we have developed a set of general recommendations for Pd-catalyzed crosscoupling reactions involving organic bases. The optimization algorithm determined that the catalyst supported by the dialkyltriarylmonophosphine ligand AlPhos was the most active in the coupling of each amine nucleophile. Furthermore, our automated optimization revealed that the phosphazene base BTTP can be used to facilitate the coupling of secondary alkylamines and aryl triflates. Chapter 4: The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C-N Cross-Coupling Palladium-catalyzed amination reactions using soluble organic bases have provided a solution to the many issues associated with heterogeneous reaction conditions. Still, homogeneous C-N crosscoupling approaches cannot yet employ bases as weak and economical as trialkylamines. Furthermore, organic base-mediated methods have not been developed for Ni(0/II) catalysis, despite some advantages of such systems over analogous Pd-based catalysts. We designed a new air-stable and easily prepared Ni(II) precatalyst bearing an electron-deficient bidentate phosphine ligand that enables the cross-coupling of aryl triflates with aryl amines using triethylamine (TEA) as base. The method is tolerant of sterically-congested coupling partners, as well as those bearing base- and nucleophile-sensitive functional groups. With the aid of density functional theory (DFT) calculations, we determined that the electron-deficient auxiliary ligands decrease both the pK[subscript a] of the Ni-bound amine and the barrier to reductive elimination from the resultant Ni(II)-amido complex. Moreover, we determined that precluding Lewis acid-base complexation between the Ni catalyst and the base, due to steric factors, is important for avoiding catalyst inhibition.
Book Synopsis Active Pharmaceutical Ingredients in Synthesis by : Anthony J. Burke
Download or read book Active Pharmaceutical Ingredients in Synthesis written by Anthony J. Burke and published by John Wiley & Sons. This book was released on 2018-11-28 with total page 450 pages. Available in PDF, EPUB and Kindle. Book excerpt: Presents the most effective catalytic reactions in use today, with a special focus on process intensification, sustainability, waste reduction, and innovative methods This book demonstrates the importance of efficient catalytic transformations for producing pharmaceutically active molecules. It presents the key catalytic reactions and the most efficient catalytic processes, including their significant advantages over compared previous methods. It also places a strong emphasis on asymmetric catalytic reactions, process intensification (PI), sustainability and waste mitigation, continuous manufacturing processes as enshrined by continuous flow catalysis, and supported catalysis. Active Pharmaceutical Ingredients in Synthesis: Catalytic Processes in Research and Development offers chapters covering: Catalysis and Prerequisites for the Modern Pharmaceutial Industry Landscape; Catalytic Process Design - The Industrial Perspective; Hydrogenation, Hydroformylation and Other Reductions; Oxidation; ; Catalytic Addition Reactions; Catalytic Cross-Coupling Reactions; Catalytic Metathesis Reactions; Catalytic Cycloaddition Reactions: Coming Full-Circle; Catalytic Cyclopropanation Reactions; Catalytic C-H insertion Reactions; Phase Transfer Catalysis; and Biocatalysis. -Provides the reader with an updated clear view of the current state of the challenging field of catalysis for API production -Focuses on the application of catalytic methods for the synthesis of known APIs -Presents every key reaction, including Diels-Alder, CH Insertions, Metal-catalytic coupling-reactions, and many more -Includes recent patent literature for completeness Covering a topic of great interest for synthetic chemists and R&D researchers in the pharmaceutical industry, Active Pharmaceutical Ingredients in Synthesis: Catalytic Processes in Research and Development is a must-read for every synthetic chemist working with APIs.
Book Synopsis Metal-catalyzed Cross-coupling Reactions by : François Diederich
Download or read book Metal-catalyzed Cross-coupling Reactions written by François Diederich and published by John Wiley & Sons. This book was released on 2008-07-11 with total page 540 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbon-carbon bond forming reactions are arguably the most important processes in chemistry, as they represent key steps in the building of complex molecules from simple precursors. Among these reactions, metal-catalyzed cross-coupling reactions are extensively employed in a wide range of areas of preparative organic chemistry, ranging from the synthesis of complex natural products, to supramolecular chemistry, and materials science. In this work, a dozen internationally renowned experts and leaders in the field bring the reader up to date by documenting and critically analyzing current developments and uses of metal-catalyzed cross-coupling reactions. A particularly attractive and useful feature, that enhances the practical value of this monograph, is the inclusion of key synthetic protocols, in experimental format, chosen for broad utility and application. This practice-oriented book can offer the practitioner short cuts to ensure they remain up-to-date with the latest developments.
Book Synopsis Suzuki–Miyaura Cross- Coupling Reaction and Potential Applications by : Ioannis D. Kostas
Download or read book Suzuki–Miyaura Cross- Coupling Reaction and Potential Applications written by Ioannis D. Kostas and published by MDPI. This book was released on 2018-03-23 with total page 273 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book is a printed edition of the Special Issue "Suzuki–Miyaura Cross-Coupling Reaction and Potential Applications" that was published in Catalysts
Book Synopsis Arene Chemistry by : Jacques Mortier
Download or read book Arene Chemistry written by Jacques Mortier and published by John Wiley & Sons. This book was released on 2015-12-14 with total page 987 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organized to enable students and synthetic chemists to understand and expand on aromatic reactions covered in foundation courses, the book offers a thorough and accessible mechanistic explanation of aromatic reactions involving arene compounds. • Surveys methods used for preparing arene compounds and their transformations • Connects reactivity and methodology with mechanism • Helps readers apply aromatic reactions in a practical context by designing syntheses • Provides essential information about techniques used to determine reaction mechanisms
Book Synopsis Synthetic Applications by : Rajender S. Varma
Download or read book Synthetic Applications written by Rajender S. Varma and published by Walter de Gruyter GmbH & Co KG. This book was released on 2022-05-09 with total page 578 pages. Available in PDF, EPUB and Kindle. Book excerpt: Magnetic nanocatalysts are becoming an important tool for greener catalytic processes in chemical transformations in view of the ease of their removal from a reaction medium. This book explores assorted magnetic nanocatalysts, their deployment in synthesis, chemical transformation and their recovery and reuse. Various thematic topics embodied include magnetic nanocatalysts for S-S bond formation, N-heterocycle formation, C-heteroatom bond formation, silica-supported catalysts, multicomponent reactions, including their recyclability; another available volume emphasizes the utility of magnetic nanocatalysts in industrial appliances.
Book Synopsis The Stille Reaction by : Vittorio Farina
Download or read book The Stille Reaction written by Vittorio Farina and published by John Wiley & Sons. This book was released on 1998-09-18 with total page 676 pages. Available in PDF, EPUB and Kindle. Book excerpt: Die Stille-Reaktion ist eine der sehr wenigen Reaktionen, in denen unter milden Bedingungen Kohlenstoff-Kohlenstoff-Bindungen geknüpft werden können. Man verwendet die Reaktion häufig in der Synthese komplizierter Moleküle zur Verknüpfung größerer Molekülbausteine. Die Autoren diskutieren vom präparativen Standpunkt aus Grenzen, Einflüsse, strukturelle Effekte und die Wahl der geeigneten Reaktionsbedingungen. Mit ausführlichen Vorschriften und vielen Beispielen. (11/98)
Book Synopsis Nickel- and Palladium-Catalyzed Cross Coupling Reactions by : Rebecca Green
Download or read book Nickel- and Palladium-Catalyzed Cross Coupling Reactions written by Rebecca Green and published by . This book was released on 2016 with total page 183 pages. Available in PDF, EPUB and Kindle. Book excerpt: The following dissertation discusses the development of a nickel catalyst for the synthesis of Csp2-Csp bonds in addition to the development and mechanistic studies of nickel and palladium catalysts for the synthesis of Csp2-N bonds. The first chapter is a review of the cross-coupling reactions discussed in this dissertation. Nickel and palladium will be compared with respect to physical properties and reactivity differences. The challenges associated with nickel-catalyzed cross coupling will be illustrated, while drawing analogies to analogous palladium-catalyzed reactions. The literature background for the synthesis of Csp2-Csp bonds, catalyzed by palladium and palladium/copper catalytic systems, will be reviewed, while highlighting the challenges and limitations of the field. The field of Csp2-N bond-forming reactions will be examined, as the differences in reactivity between nickel and palladium will be emphasized. Chapter 2 discusses our efforts towards the development of a nickel catalyst for the development of a Csp2-Csp bond forming reaction, performed in the absence of a copper co-catalyst. Chapter 3 describes the development of a single-component nickel complex that catalyzes the coupling of aryl chlorides with primary alkylamines. A series of mechanistic experiments, including synthesis of catalytic intermediates and kinetic experiments, were performed to elucidate the mechanism of the reaction. Chapter 4 discusses our report the palladium-catalyzed coupling of aryl halides withammonia and gaseous amines as their ammonium salts. A difference in selectivity between reactions of aryl chlorides and aryl bromides was discovered and investigated. Chapter 5 describes the development of a single-component nickel catalyst for the coupling of aryl chlorides with ammonia and ammonium sulfate to form the corresponding primary arylamines. The application of ammonium salts was extended to the coupling of gaseous amines, such as methylamine and ethylamine, which were subjected to the reaction conditions as their hydrochloride salt.
Book Synopsis Mechanistic Studies on Palladium-catalyzed Coupling Reactions by : Bradley P. Carrow
Download or read book Mechanistic Studies on Palladium-catalyzed Coupling Reactions written by Bradley P. Carrow and published by . This book was released on 2011 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
