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The Development And Mechanistic Studies Of Palladium Catalyzed Hydroamination And Metal Free Oxidative Amination Reactions
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Book Synopsis The Development and Mechanistic Studies of Palladium Catalyzed Hydroamination and Metal-free Oxidative Amination Reactions by : Brian M. Cochran
Download or read book The Development and Mechanistic Studies of Palladium Catalyzed Hydroamination and Metal-free Oxidative Amination Reactions written by Brian M. Cochran and published by . This book was released on 2009 with total page 612 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Development, Application and Mechanistic Investigation of Palladium Catalyzed Aerobic Oxidative Amination Methods by :
Download or read book Development, Application and Mechanistic Investigation of Palladium Catalyzed Aerobic Oxidative Amination Methods written by and published by . This book was released on 2014 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Palladium catalyzed oxidative transformations that employ readily available molecular oxygen as the stoichiometric oxidant enable economic synthetic routes to complex organic targets. This thesis focuses on the development of aerobic oxidative transformations that generate carbon-nitrogen bonds. Chapters 2 and 3 describe research projects that have expanded the scope and mechanistic understanding of reactions that involve amidopalladation of alkenes (aza-Wacker reactions). Chapters 4, 5 and 6 describe research projects that have targeted the discovery of aryl C-H amination reactions. Palladium catalyzed aerobic C-H amination reactions have limited precedent. Several approaches to address this challenge were tested, and promising results are discussed.
Book Synopsis Palladium Catalyzed Oxidation of Hydrocarbons by : P. Henry
Download or read book Palladium Catalyzed Oxidation of Hydrocarbons written by P. Henry and published by Springer Science & Business Media. This book was released on 2012-12-06 with total page 449 pages. Available in PDF, EPUB and Kindle. Book excerpt: The field of organometallic chemistry has emerged over the last twenty-five years or so to become one of the most important areas of chemistry, and there are no signs of abatement in the intense current interest in the subject, particularly in terms of its proven and potential application in catalytic reactions involving hydrocarbons. The development of the organometallic/ catalysis area has resulted in no small way from many contributions from researchers investigating palladium systems. Even to the well-initiated, there seems a bewildering and diverse variety of organic reactions that are promoted by palladium(II) salts and complexes. Such homogeneous reactions include oxidative and nonoxidative coupling of substrates such as olefins, dienes, acetylenes, and aromatics; and various isomerization, disproportionation, hydrogenation, dehydrogenation, car bonylation and decarbonylation reactions, as well as reactions involving formation of bonds between carbon and halogen, nitrogen, sulfur, and silicon. The books by Peter M. Maitlis - The Organic Chemistry of Palladium, Volumes I, II, Academic Press, 1971 - serve to classify and identify the wide variety of reactions, and access to the vast literature is available through these volumes and more recent reviews, including those of J. Tsuji [Accounts Chem. Res. , 6, 8 (1973); Adv. in Organometal. , 17, 141 (1979)], R. F. Heck [Adv. in Catat. , 26, 323 (1977)], and ones by Henry [Accounts Chem. Res. , 6, 16 (1973); Adv. in Organometal. , 13, 363 (1975)]. F. R. Hartley's book - The Chemistry of Platinum and Palladium, App!. Sci. Pub!.
Book Synopsis Mechanistic Studies of Palladium-catalyzed "Wacker-type" Intramolecular Aerobic Oxidative Amination of Alkenes and Development of Safe and Scalable Continuous-flow Methods for Palladium-catalyzed Aerobic Oxidation by : Xuan Ye
Download or read book Mechanistic Studies of Palladium-catalyzed "Wacker-type" Intramolecular Aerobic Oxidative Amination of Alkenes and Development of Safe and Scalable Continuous-flow Methods for Palladium-catalyzed Aerobic Oxidation written by Xuan Ye and published by . This book was released on 2010 with total page 219 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Palladium and Nickel Catalyzed Transformations Forming Functionalized Heterocycles by : Hyung Yoon
Download or read book Palladium and Nickel Catalyzed Transformations Forming Functionalized Heterocycles written by Hyung Yoon and published by Springer Nature. This book was released on 2020-09-02 with total page 236 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book presents Pd- and Ni-catalyzed transformations generating functionalized heterocycles. Transition metal catalysis is at the forefront of synthetic organic chemistry since it offers new and powerful methods to forge carbon–carbon bonds in high atom- and step-economy. In Chapter 1, the author describes a Pd- and Ni-catalyzed cycloisomerization of aryl iodides to alkyl iodides, known as carboiodination. In the context of the Pd-catalyzed variant, the chapter explores the production of enantioenriched carboxamides through diastereoselective Pd-catalyzed carboiodination. It then discusses Ni-catalyzed reactions to generate oxindoles and an enantioselective variant employing a dual ligand system. Chapter 2 introduces readers to a Pd-catalyzed diastereoselective anion-capture cascade. It also examines diastereoselective Pd-catalyzed aryl cyanation to synthesize alkyl nitriles, a method that generates high yields of borylated chromans as a single diastereomer, and highlights its synthetic utility. Lastly, Chapter 3 presents a Pd-catalyzed domino process harnessing carbopalladation, C–H activation and π-system insertion (benzynes and alkynes) to generate spirocycles. It also describes the mechanistic studies performed on these reactions.
Book Synopsis Mechanistic Studies and Catalyst Development of Palladium-catalyzed Aerobic C-h Oxidations of (hetero)aromatics by : Dian Wang
Download or read book Mechanistic Studies and Catalyst Development of Palladium-catalyzed Aerobic C-h Oxidations of (hetero)aromatics written by Dian Wang and published by . This book was released on 2017 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: The selective oxidation of C-H bonds in (hetero)aromatics provides an efficient access to functionalized aromatic molecules of industrial interest. Aerobic oxygen is an ideal terminal oxidants for this transformation because it is readily available and often produces water as the sole byproduct. Homogeneous palladium catalysts are eminently compatible with aerobic turnovers and have seen success in numerous aerobic oxidation processes (e. g., alkene oxidation, alcohol oxidation). In contrast, palladium-catalyzed aerobic oxidative C-H functionalization has been rather underdeveloped. Challenges include slow catalytic turnover, catalyst decomposition and lack of selectivity control (e.g., site selectivity, homo- vs. cross-coupling selectivity). This thesis presents three research projects with different approaches to tackle the unsolved problems in the reaction class of palladium-catalyzed aerobic C-H oxidation of (hetero)aromatics. The reaction mechanism of C-H/C-H coupling of [o]-xylene was characterized, which disclosed a novel, bimetallic pathway. Built on this work, the effect of copper cocatalyst in this reaction was investigated, which revealed a non-traditional role of copper salt in oxidative palladium catalysis and led to the discovery of an improved catalyst system. Last, a synthetic methodology for aerobic indole C-H arylation with ligand-controlled site selectivity was developed, which provided efficient access to pharmaceutically-relevant aryl indoles and led to preliminary mechanistic insights into regiocontrol.
Book Synopsis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis by : Montserrat Diéguez
Download or read book Artificial Metalloenzymes and MetalloDNAzymes in Catalysis written by Montserrat Diéguez and published by John Wiley & Sons. This book was released on 2018-02-21 with total page 431 pages. Available in PDF, EPUB and Kindle. Book excerpt: An important reference for researchers in the field of metal-enzyme hybrid catalysis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a comprehensive review of the most current strategies, developed over recent decades, for the design, synthesis, and optimization of these hybrid catalysts as well as material about their application. The contributors—noted experts in the field—present information on the preparation, characterization, and optimization of artificial metalloenzymes in a timely and authoritative manner. The authors present a thorough examination of this interesting new platform for catalysis that combines the excellent selective recognition/binding properties of enzymes with transition metal catalysts. The text includes information on the various applications of metal-enzyme hybrid catalysts for novel reactions, offers insights into the latest advances in the field, and contains an informative perspective on the future: Explores the development of artificial metalloenzymes, the modern and strongly evolving research field on the verge of industrial application Contains a comprehensive reference to the research area of metal-enzyme hybrid catalysis that has experienced tremendous growth in recent years Includes contributions from leading researchers in the field Shows how this new catalysis combines the selective recognition/binding properties of enzymes with transition metal catalysts Written for catalytic chemists, bioinorganic chemists, biochemists, and organic chemists, Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a unique reference to the fundamentals, concepts, applications, and the most recent developments for more efficient and sustainable synthesis.
Book Synopsis Fundamentals of Organometallic Catalysis by : Dirk Steinborn
Download or read book Fundamentals of Organometallic Catalysis written by Dirk Steinborn and published by John Wiley & Sons. This book was released on 2011-11-30 with total page 484 pages. Available in PDF, EPUB and Kindle. Book excerpt: Vor allem an Studenten fortgeschrittener Semester und Doktoranden gerichtet ist dieses Lehrbuch der Katalyse mit metallorganischen Verbindungen, das auch biologisch relevanten Reaktionen viel Platz einräumt. Hervorragend zum Selbststudium geeignet - mit zahlreichen Übungsaufgaben, nach Schwierigkeitsgraden geordnet und durch Lösungen ergänzt.
Book Synopsis Method Development and Mechanistic Investigation of Palladium-catalyzed Allylic Oxidation Reactions of Terminal Alkenes by : Caitlin Kozack
Download or read book Method Development and Mechanistic Investigation of Palladium-catalyzed Allylic Oxidation Reactions of Terminal Alkenes written by Caitlin Kozack and published by . This book was released on 2021 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Palladium-catalyzed allylic C-H acetoxylation has been the subject of significant study in its 60-year history, however several limitations still exist. There are no methods for the allylic acetoxylation of terminal alkenes that exhibit high catalytic turnover. This is of considerable interest in order to establish large scale reactions. Reactions with a broad scope in substrate and coupling partner are also relatively sparse. In order for the field to continue to move forward, it is critical to understand the mechanistic systems so the insights can be applied to develop new methods that are broad in scope and robust in catalytic activity. This thesis will focus on mechanistic investigations to understand the mechanism of 4,5-diazafluoren-one (DAF)/Pd(OAc)[2]-catalyzed aerobic allylic C-H acetoxylation reactions, as well as develop methods that will expand the scope and increase the catalytic activity of allylic acetoxylation.Chapter 1 analyzes high turnover methods for Pd-catalyzed allylic acetoxylation with a focus on the factors that contribute to the success of existing catalytically robust methods, as well as the challenges with developing high turnover methods for terminal akenes and how recent advances with this substrate class may provide insights into unlocking reactivity. Chapter 2 presents the development of a method for Pd-catalyzed aerobic allylic acyloxylation with a low stoichiometry of carboxylic acid coupling partners. Chapter 3 provides an in-depth mechanistic investigation into 4,5-diazafluoren-9-one (DAF)/Pd(OAc)[2]-catalyzed aerobic allylic C-H acetoxylation by using operands spectroscopy to elucidate the two distinct rate regimes. Chapter 4 probes the role of benzoquinone additives in DAF/Pd(OAc)[2]-catalyzed aerobic allylic acetoxylation in the presence and absence of Co(salophen), a transition metal cocatalyst. Chapter 5 presents the development of a method for high turnover DAF/Pd(OAc)[2]-catalyzed allylic C-H acetoxylation of a terminal alkene as well as preliminary kinetics to probe the mechanism.
Book Synopsis Mechanistic Studies on Palladium-catalyzed Carbon-nitrogen Bond Forming Reactions by : Liane May Klingensmith
Download or read book Mechanistic Studies on Palladium-catalyzed Carbon-nitrogen Bond Forming Reactions written by Liane May Klingensmith and published by . This book was released on 2005 with total page 138 pages. Available in PDF, EPUB and Kindle. Book excerpt: Precatalyst species present in a solution of Pd2(dba)3 and Xantphos were identified as Pd(Xantphos)(dba) and Pd(Xantphos)2 by use of 31p NMR and independent syntheses. Pd(Xantphos)2 was found to form at high ligand concentrations. To determine whether the formation of this species affected reaction rates, reaction calorimetry was used to explore the rate of the palladium-catalyzed coupling of 4-t-butylbromobenzene and morpholine using the ligand Xantphos at varying palladium to ligand ratios. It was found that catalyst activity is dramatically dependent on the concentration of ligand relative to palladium, due to formation of Pd(Xantphos)2. Two plausible hypotheses for the low activity of Pd(Xantphos)2 as a precatalyst are (1) a slow rate of dissociation of a ligand from the bis-ligated species, and (2) the high degree of insolubility of Pd(Xantphos)2. Magnetization transfer experiments were used to probe the rate of dissociation of ligand for the bis-ligated species, and reaction calorimetry experiments were performed using the more soluble t-butylXantphos in comparison to Xantphos to determine whether the insolubility of' Pd(Xantphos)2 causes it to have relatively low activity. It was found that solubility is not the main cause for the low activity of Pd(Xantphos)2, and evidence was given to support the hypothesis that low activity results from the slow dissociation of a ligand from the bis-ligated species.
Book Synopsis Palladium Catalyzed Amination of Olefins by : Jodie Lynn Brice
Download or read book Palladium Catalyzed Amination of Olefins written by Jodie Lynn Brice and published by . This book was released on 2006 with total page 274 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Mechanistic Studies of Palladium-catalyzed Aerobic Alcohol Oxidation by : Bradley A. Steinhoff
Download or read book Mechanistic Studies of Palladium-catalyzed Aerobic Alcohol Oxidation written by Bradley A. Steinhoff and published by . This book was released on 2005 with total page 254 pages. Available in PDF, EPUB and Kindle. Book excerpt:
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 Strategies for Palladium-Catalyzed Non-directed and Directed C bond H Bond Functionalization by : Anant R. Kapdi
Download or read book Strategies for Palladium-Catalyzed Non-directed and Directed C bond H Bond Functionalization written by Anant R. Kapdi and published by Elsevier. This book was released on 2017-05-25 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Strategies for Palladium-Catalyzed Non-directed and Directed C-H Bond Functionalization portrays the complete scope of these two aspects of C-H bond functionalization in a single volume for the first time. Featured topics include the influence of palladacyclic systems in C-H bond functionalization (need for newer catalytic systems for better efficiency), mechanistic aspect of the functionalization strategies leading to better systems, and applications of these methodologies to natural product synthesis and material synthesis.
Book Synopsis Palladium-based Catalyst for Heterogeneous Photocatalysis by : Ayda Elhage
Download or read book Palladium-based Catalyst for Heterogeneous Photocatalysis written by Ayda Elhage and published by . This book was released on 2019 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Over the past decade, heterogeneous photocatalysis have gained lots of interest and attention among the organic chemistry community due to its applicability as an alternative to its homogeneous counterpart. Heterogeneous catalysis offers the advantages of easy separation and reusability of the catalyst. Several studies showed that under optimized conditions, efficient and highly selective catalytic systems could be developed using supported metal/metal oxide nanoparticles. In this dissertation, we summarize the progress in the development of supported palladium nanoparticles for different types of organic reactions. Palladium-decorated TiO2 is a moisture, air-tolerant, and versatile catalyst. The direct excitation of Pd nanoparticles selectively isomerized the benzyl-substituted alkenes to phenyl-substituted alkenes (E-isomer) with complete conversion over Pd@TiO2 under H2-free conditions. Likewise, light excited Pd nanoparticles catalyzed Sonogashira coupling, a C-C coupling reaction between different aryl iodides and acetylenes under very mild conditions in short reaction times. On the other hand, UV irradiation of Pd@TiO2 in alcoholic solutions promotes alkenes hydrogenation at room temperature under Argon. Thus, The photocatalytic activity of Pd@TiO2 can be easily tuned by changing the irradiation wavelength. Nevertheless, some of these systems suffer from catalyst deactivation, one of the main challenges faced in heterogeneous catalysis that decreases the reusability potential of the materials. In order to overcome this problem, we developed an innovative method called "Catalytic Farming". Our reactivation strategy is based on the crop rotation system used in agriculture. Thus, alternating different catalytic reactions using the same catalyst can reactivate the catalyst surface by restoring its oxidation states and extend the catalyst lifetime along with its selectivity and efficiency. In this work, the rotation strategy is illustrated by Sonogashira coupling -problem reaction that depletes the catalyst- and Ullmann homocoupling -plausible recovery reaction that restores the oxidation state of the catalyst (Pd@TiO2). The selection of the reactions in this approach is based on mechanistic studies that include the role of the solvent and evaluation of the palladium oxidation state after each reaction. In a more exploratory analysis, we successfully demonstrated that Pd nanoparticles could be supported in a wide range of materials, including inert ones such as nanodiamonds or glass fibers. The study of the action spectrum shows that direct excitation of the Pd nanoparticles is a requisite for Sonogashira coupling reactions. The main advantages of heterogeneous catalysis compared to its homogeneous counterpart are easy separation and reusability of the catalyst. Finally in order to facilitate catalyst separation from batch reaction and develop a suitable catalytic system for continuous flow chemistry, we employed glass fibers as catalyst support for a wide variety of thermal and photochemical organic reactions including C-C coupling, dehalogenation and cycloaddition. Different metal/metal oxide nanoparticles, namely Pd, Co, Cu, Au, and Ru were deposited on glass wool and fully characterized. As a proof of concept, Pd decorated glass fibers were employed in heterogeneous flow photocatalysis for Sonogashira coupling and reductive de-halogenation of aryl iodides.
Book Synopsis New Palladium Catalyzed Carbonylative Approaches to Heterocycle and Acid Chloride Synthesis by : Gerardo Martin Torres
Download or read book New Palladium Catalyzed Carbonylative Approaches to Heterocycle and Acid Chloride Synthesis written by Gerardo Martin Torres and published by . This book was released on 2020 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: "Metal catalyzed carbonylation reactions are heavily exploited in synthetic chemistry. These include not only high volume industrial reactions, but also a plethora of catalytic small molecule syntheses. This thesis will describe our efforts to develop such reactions. In these, palladium catalyzed carbonylations are exploited to build-up reactive products such as acid chlorides or carbonyl-containing 1,3-dipoles. Coupling this with the ability of the products undergo other spontaneous reactions can offer new routes to build up products from combinations of available reagents or be used to expand the scope of carbonylation chemistry. In chapter 2, we describe how the palladium catalyzed carbonylation of aryl iodides in the presence of imines can allow the overall generation of a 1,3-dipole: a Münchnone. A variety of mechanistic studies were performed on this reaction and show that it proceeds via a tandem catalytic process: the first involving the Pd catalyzed coupling of aryl iodides with carbon monoxide and a chloride salt to form an acid chloride, which can react with an imine and then undergo a second spontaneous cyclocarbonylation to afford the product. Coupling their formation with alkyne cycloaddition can be used to develop a novel method to assemble broad families of pyrroles from aryl iodides, imines, carbon monoxide and alkynes. In Chapter 3 we develop a strategy to apply our palladium catalyzed carbonylative synthesis of Münchnones to construct more complex pyrrole structures. In this, the combination of alkyne-tethered imines, aryl iodides, and carbon monoxide generates a Münchnone that can undergo intramolecular 1,3-dipolar cycloaddition to generate polycyclic pyrroles. This approach allows the modular and regioselective synthesis of complex pyrrole structures, and is compatible with less activated alkynes. In addition, we show that this reaction can be used in tandem with the palladium catalyzed Sonogashira functionalization of terminal alkynes with aryl iodides.In Chapter 4 we describe our efforts to take advantage of the ketene-like reactivity of Münchnones to generate [beta]-lactams. This transformation occurs via the palladium catalyzed formation of Münchnones from imines, aryl iodides, and carbon monoxide, followed by a cycloaddition to a second equivalent of imine to afford amide substituted [beta]-lactam products. Moreover, applying the conditions described in Chapter 2 for the synthesis of Münchnones allowed us to construct more diversely substituted [beta]-lactams by reacting the Münchnone with a different imine. Alternatively, the palladium catalyzed carbonylation of imine-tethered aryl iodides leads to the formation of novel spirocyclic [beta]-lactams.The palladium catalyzed synthesis of acid chlorides is a key component to the synthetic approaches to heterocycles presented in Chapters 2-4. However, the specific features that enable the catalyst to mediate the challenging reductive elimination of acid chlorides also inhibit the reverse oxidative addition step. In Chapter 5 we address these limitations by approaching this palladium catalyzed reaction from a different perspective. In this, visible light is used to drive both key steps in palladium catalysis: oxidative addition and reductive elimination. Analogous to other reports, we show that visible light excitation of a Pd complex can drive oxidative addition of a wide variety of aryl and alkyl halides. In addition, we find that visible light can induce a new reaction step the reductive elimination of acid chlorides. The latter occurs via the excitation in this case of the palladium-acyl intermediate. Together, this offers a platform to perform palladium catalyzed carbonylations at ambient temperature, with a wide array of organic halide substrates that have proven to be challenging in traditional palladium catalysis, and form from these acid chloride electrophiles that can allow the use of nucleophiles that are typically incompatible with carbonylations"--
Book Synopsis Mechanism of the Palladium-catalyzed Amination of Aryl Halides by : Luis Manuel Alcaźar-Romań
Download or read book Mechanism of the Palladium-catalyzed Amination of Aryl Halides written by Luis Manuel Alcaźar-Romań and published by . This book was released on 2001 with total page 472 pages. Available in PDF, EPUB and Kindle. Book excerpt:
