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The Design And Development Of Palladium Catalyzed Aerobic Oxidative Transformations
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Book Synopsis The Design and Development of Palladium-catalyzed Aerobic Oxidative Transformations by : Eric Matthew Ferreira
Download or read book The Design and Development of Palladium-catalyzed Aerobic Oxidative Transformations written by Eric Matthew Ferreira and published by . This book was released on 2005 with total page 1312 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 The Design of Palladium and Copper-catalyzed Atom- Economical Reactions by : Boran Xu
Download or read book The Design of Palladium and Copper-catalyzed Atom- Economical Reactions written by Boran Xu and published by . This book was released on 2016 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: "This thesis describes the development of novel metal-catalyzed reactions in two different areas: palladium-catalyzed multicomponent coupling reactions, and copper-catalyzed aerobic oxidations of alcohols and amines. The goal of this work is to discover efficient processes to rapidly generate useful products with minimal waste. In chapter 2, we describe a straightforward new synthesis of 2-imidazolines. This reaction couples the palladium-catalyzed multicomponent formation of 2-imidazolium carboxylates, with subsequent decarboxylation. Polysubstituted imidazolines have useful applications in therapeutics, but are typically prepared in a multistep sequence. We report that the use benzoic acid and water as additives affords good yields and diastereoselectivities for the decarboxylation step. Combining this reaction with subsequent nitrogen deprotection, allows access to imidazolines from four available reagents: two imines, an acid chloride and CO. In chapter 3, we describe the three component palladium-catalyzed synthesis of [alpha]-amidostannanes from imines, acid chlorides and a bis-stannane. The reaction affords product in good yields, proceeds in 1 h, and uses simple Pd2(dba)3 as the catalyst. Mechanistically, this transformation occurs via a Stille-type cross-coupling of an in situ generated iminium salt with the bis-stannane. This represents a mild alternative to traditional syntheses of these products, with strong nucleophilic reagents. Subsequent lithiation and carboxylation can generate various [alpha]-amino acid derivatives in two steps from imines, acid chlorides and CO2. In chapter 4, we describe the copper-catalyzed aerobic oxidation of alcohols without the use nitroxyl co-catalysts. We demonstrate that a Cu/di-tert-butylethylenediamine (DBED) catalyst can generate active copper-oxygen species capable of mediating alcohol oxidation. This catalyst operates at ambient pressure and temperature and retains activity for challenging substrates such as secondary unactivated alcohols. Notably, this system likely operates via a distinct mechanistic pathway compared to nitroxyl based oxidations, and as a result, shows different alcohol chemoselectivity. In chapter 5, we describe the effects of the counterion (X-) in copper-catalyzed aerobic oxidation, and apply these to the oxidation of primary amines. By manipulating the copper salt employed, we have been able to design active catalysts for the oxidation of amines to nitriles (with CuI/DBED), or to imines (with CuPF6). Both of these reactions occur at unusually mild conditions (ambient temperature and pressure), and provide a practical approach to selective amine oxidation without added nitroxyl co-catalysts. " --
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 194 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 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 1. Axially-chiral 7-membered N-heterocyclic Carbenes : Synthesis and Application to Palladium-catalyzed Intramolecular Aerobic Oxidation of Olefins by : Christopher C. Scarborough
Download or read book 1. Axially-chiral 7-membered N-heterocyclic Carbenes : Synthesis and Application to Palladium-catalyzed Intramolecular Aerobic Oxidation of Olefins written by Christopher C. Scarborough and published by . This book was released on 2008 with total page 474 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Catalytic Aerobic Oxidations by : Esteban Mejía
Download or read book Catalytic Aerobic Oxidations written by Esteban Mejía and published by Royal Society of Chemistry. This book was released on 2020-07-14 with total page 349 pages. Available in PDF, EPUB and Kindle. Book excerpt: Oxidation reactions are an important chemical transformation in both academia and industry. Among the major advances in the field has been the development of catalytic processes, which are not only selective and efficient, but also allow the replacement of common stoichiometric oxidants with molecular oxygen, ideally from air at atmospheric pressure. This results in processes with higher atom efficiency, where water is the only side product in line with the principles of green chemistry. Focusing on the use of molecular oxygen as the terminal oxidant, this book covers recent advances in both heterogeneous and homogeneous systems, with and without metals and on the “taming” of the highly reactive oxygen gas by use of micro-flow reactors and membranes. A useful reference for industrial and academic chemists working on oxidation processes, as well as green chemists.
Book Synopsis Elucidating the Mechanisms of Copper-catalyzed Aerobic Transformations by :
Download or read book Elucidating the Mechanisms of Copper-catalyzed Aerobic Transformations written by and published by . This book was released on 2014 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: The selective oxidation of organic molecules is a key challenge in the transformation of simple hydrocarbons to functionalized products. Copper catalysts are effective for the aerobic oxidations of organic substrates, including carbon-heteroatom bond-forming reactions and selective alcohol oxidations. Rigorous mechanistic understanding of these catalysts have more recently begun to guide reaction development of new classes of reactivity. The copper(II)-catalyzed oxidative coupling of boronic acids and heteroatom nucleophiles, the Chan-Evans-Lam reaction, is an alternative to non-oxidative cross-coupling technologies. Kinetic and spectroscopic (UV-visible, EPR, NMR) analysis of the reaction of 4-tolylboronic acid with methanol provides insight on the catalyst resting state(s) and steps preceding transmetalation (Chapter 2). The Chan-Lam reaction has an unpredictable substrate scope, and our results (Chapter 3) begin to rationalize the factors that govern the nucleophile reactivity, highlighting the inhibitory role of coordinating nucleophiles. Acidic nucleophiles form coupling products without interacting with the catalyst resting state. These results are in contrast to cross-coupling strategies, which are accelerated by coordination of donating nucleophiles. Homogeneous Cu/TEMPO catalysts have emerged as versatile and practical systems for aerobic alcohol oxidation. Our group has developed a CuI/TEMPO catalyst that oxidizes 1° aliphatic and benzylic alcohols with ambient air. Spectroscopic and kinetic measurements outline a two-stage mechanism that explains observed reactivity and directs further catalyst development (Chapter 4). CuI and TEMPO-H aerobic oxidation to make CuII and TEMPO, and substrate oxidation involving reaction of a CuII-alkoxide and TEMPO to make aldehyde, and reduced catalyst. Computational investigation (Chapter 5) of the substrate oxidation suggests TEMPO coordination to form a transient intermediate followed by facile hydride transfer.
Book Synopsis Development of Palladium(II)-catalyzed Methods for Alkene Functionalization by : Michelle Monnens Rogers
Download or read book Development of Palladium(II)-catalyzed Methods for Alkene Functionalization written by Michelle Monnens Rogers and published by . This book was released on 2007 with total page 380 pages. Available in PDF, EPUB and Kindle. Book excerpt:
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 1979-12-31 with total page 458 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 Palladium Catalyzed Aerobic Oxidation of Alcohols by : Lukas John
Download or read book Palladium Catalyzed Aerobic Oxidation of Alcohols written by Lukas John and published by . This book was released on 2013 with total page 74 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Journal by : American Chemical Society
Download or read book Journal written by American Chemical Society and published by . This book was released on 2004 with total page 1450 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis The Development of Palladium- and Copper-catalyzed Transformations for the Asymmetric Synthesis of Biologically Active Small Molecules by : James Thomas Masters
Download or read book The Development of Palladium- and Copper-catalyzed Transformations for the Asymmetric Synthesis of Biologically Active Small Molecules written by James Thomas Masters and published by . This book was released on 2016 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The continued demand for efficient chemo-, regio-, and stereoselective organic transformations motivates the development of new chemical reactions. Transition metal catalysis represents a powerful method for the construction of carbon-carbon, carbon-hydrogen, and carbon-heteroatom bonds in a highly selective fashion. This dissertation describes the development of several new transition metal-catalyzed organic reactions useful in the preparation of various chiral small molecules, including both fundamental organic "building block" compounds and structurally complex natural products and pharmaceutical agents. We report a new strategy for the synthesis of chiral beta-alkynyl esters, ketones, and sulfones via sequential palladium-catalyzed carbon-carbon bond formation and copper-catalyzed carbon-hydrogen bond formation. The process is operationally straightforward, compatible with a broad range of substrates, and delivers the targets in high yields with excellent levels of enantioselectivity. It is compatible with both oxygen and nitrogen functionality, and this enabled the rapid elaboration of the products into a diverse set of chiral heterocycles. The sequential catalysis protocol was employed in a concise, enantioselective synthesis of AMG 837, a potent agonist of G-protein coupled receptor 40. Recognizing both the biological relevance of chiral alkaloids and the synthetic challenges associated with the construction of quaternary, all-carbon stereocenters, we pursued a palladium-catalyzed asymmetric allylic alkylation that effected carbon-carbon bond formation on prochiral oxindole nucleophiles. Although prior research has demonstrated that allylic alkylation reactions of geminal dicarboxylate electrophiles typically yield branched products as the result of ipso-addition, we identify conditions wherein oxindoles react with a dipivaloyl electrophile to afford linear enol pivalate compounds. A mild hydrolysis reaction converts these products into the aldehyde that formally results from asymmetric conjugate addition to acrolein, a challenging transformation with limited literature precedent. These adducts are established precursors to tricyclic alkaloid scaffolds of pharmaceutical interest. Chiral gamma-heteroatom-substituted cycloalkenones are well-established organic "building blocks" that are widely used in the synthesis of complex molecules. The exposure of meso-1,4-allylic dibenzoates to chiral phosphine-ligated palladium salts in the presence of a potassium nitronate nucleophile promotes a unique oxidative desymmetrization reaction. This process yields enantiopure gamma-benzoyloxy cyclopentenones, cyclohexenones, and cycloheptenones. We describe the elaboration of these products into diverse, enantioenriched oxygen- and nitrogen-substituted cycloalkenones via subsequent palladium-catalyzed allylic alkylation reactions involving heteroatom nucleophiles. Separately, we employ enantiopure gamma-benzoyloxy cyclohexenones in short, asymmetric syntheses of enantio- and diastereomerically diverse epoxyquinoid natural products. We further highlight the utility of palladium catalysis in complex molecule synthesis through the development of a unique, intramolecular carbon-carbon bond-forming reaction that generates a strained enyne and through an asymmetric formal synthesis of aliskiren, a renin inhibitor used in the treatment of hypertension.
Book Synopsis The Mizoroki-Heck Reaction by : Martin Oestreich
Download or read book The Mizoroki-Heck Reaction written by Martin Oestreich and published by John Wiley & Sons. This book was released on 2009-02-11 with total page 608 pages. Available in PDF, EPUB and Kindle. Book excerpt: Exploring the importance of Richard F. Heck’s carbon coupling reaction, this book highlights the subject of the 2010 Nobel Prize in Chemistry for palladium-catalyzed cross couplings in organic synthesis, and includes a foreword from Nobel Prize winner Richard F. Heck. The Mizoroki-Heck reaction is a palladium-catalyzed carbon–carbon bond forming process which is widely used in organic and organometallic synthesis. It has seen increasing use in the past decade as chemists look for strategies enabling the controlled construction of complex carbon skeletons. The Mizoroki-Heck Reaction is the first dedicated volume on this important reaction, including topics on: mechanisms of the Mizoroki-Heck reaction intermolecular Mizoroki-Heck reactions focus on regioselectivity and product outcome in organic synthesis waste-minimized Mizoroki-Heck reactions intramolecular Mizoroki-Heck reactions formation of heterocycles chelation-controlled Mizoroki-Heck reactions the Mizoroki-Heck reaction in domino processes oxidative heck-type reactions (Fujiwara-Moritani reactions) Mizoroki-Heck reactions with metals other than palladium ligand design for intermolecular asymmetric Mizoroki-Heck reactions intramolecular enantioselective Mizoroki-Heck reactions desymmetrizing Mizoroki-Heck reactions applications in combinatorial and solid phase syntheses, and the development of modern solvent systems and reaction techniques the asymmetric intramolecular Mizoroki-Heck reaction in natural product total synthesis Several chapters are devoted to asymmetric Heck reactions with particular focus on the construction of otherwise difficult-to-obtain sterically congested tertiary and quaternary carbons. Industrial and academic applications are highlighted in the final section. The Mizoroki-Heck Reaction will find a place on the bookshelves of any organic or organometallic chemist. “I am convinced that this book will rapidly become the most important reference text for research chemists in academia and industry who seek orientation in the rapidly growing and – for the layman – confusing field described as the “’Mizoroki–Heck reaction’.” (Synthesis, March 2010)
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 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 Oxidative Cross-Coupling Reactions by : Aiwen Lei
Download or read book Oxidative Cross-Coupling Reactions written by Aiwen Lei and published by John Wiley & Sons. This book was released on 2016-08-12 with total page 240 pages. Available in PDF, EPUB and Kindle. Book excerpt: The first handbook on this emerging field provides a comprehensive overview of transition metal-catalyzed coupling reactions in the presence of an oxidant. Following an introduction to the general concept and mechanism of this reaction class, the team of authors presents chapters on C-C cross-coupling reactions using organometallic partners, C-Heteroatom bond forming reactions via oxidative couplings, and C-H couplings via C-H activation. The text also covers such groundbreaking topics as recent achievements in the fields of C-C and C-X bond formation reactions as well as C-H activation involving oxidative couplings. With its novel and concise approach towards important building blocks in organic chemistry and its focus on synthetic applications, this handbook is of great interest to all synthetic chemists in academia and industry alike.
