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Hydroxylation Of Unactivated Tertiary Carbon Hydrogen Bonds Using Organic And Metal Based Catalysts
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Book Synopsis Hydroxylation of Unactivated Tertiary Carbon-hydrogen Bonds Using Organic and Metal-based Catalysts by : Ashley Margaret Adams
Download or read book Hydroxylation of Unactivated Tertiary Carbon-hydrogen Bonds Using Organic and Metal-based Catalysts written by Ashley Margaret Adams and published by . This book was released on 2015 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The selective hydroxylation of C--H bonds with complex substrates remains a grand challenge in modern synthetic chemistry. Selective methods for C--H oxidation have the potential to transform the field of natural product and complex molecule synthesis. While a variety of methods exist for the oxidation of C--H bonds, significant challenges in reaction efficiency, including catalyst turnover numbers and oxidant use, and positional selectivity still remain. One method that our laboratory has investigated for C--H hydroxylation uses 1,2,3-benzoxathiazine-2,2-dioxide-derived oxaziridines. By gaining an understanding of the off pathway processes that govern oxaziridine stability, significant improvements in reaction time, scope, and efficiency were obtained. Subsequent studies focused on elucidating the energetic requirements of the C--H bond oxidation event as well as probing the mechanism of the previously undescribed reduction of the oxaziridine intermediate in water and alcoholic solvents. The final chapter of this thesis details investigations into two metal-based approaches for catalyzing C--H hydroxylation, along with a comparative analysis of several methods for C--H hydroxylation that appear in the literature. These efforts serve to define the current scope and limitations of existing technologies for C--H hydroxylation and provide a reference for users of this technology.
Book Synopsis Hydroxylation of Unactivated Tertiary Carbon-hydrogen Bonds Using High-valent Ruthenium Catalysts by : Eric Andrew McNeill
Download or read book Hydroxylation of Unactivated Tertiary Carbon-hydrogen Bonds Using High-valent Ruthenium Catalysts written by Eric Andrew McNeill and published by . This book was released on 2012 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The prevalence of the hydroxyl group in organic molecules of synthetic and biological interest makes direct, selective hydroxylation of unactivated carbon-hydrogen (C--H) bonds in complex molecules a desirable goal. This approach to oxygen incorporation is further inspired by Nature, where enzymes mediate hydroxylation of complex substrates with exquisite selectivity. Chemists have designed catalysts for C--H hydroxylation, but further improvements in chemoselectivity, positional selectivity and turnover numbers are needed for C--H hydroxylation to become a widely-used tool for fine chemicals synthesis. Our approach to the problem of C--H hydroxylation involves the use of high-valent ruthenium oxo complexes. We have found that addition of pyridine to ruthenium tetroxide (RuO¬4, generated using ruthenium trichloride and potassium bromate) results in a notable improvement in the ability of RuO4 to catalyze C--H hydroxylation of functionalized substrates. This reaction proceeds with predictable selectivity in substrates with more than one tertiary C--H center. Incorporation of isotopically labeled oxygen into a substrate is possible using this methodology. However, the highly-oxidizing nature of RuO4 places some limits on the types of functionality that may be present in substrate molecules. Limitations of the ruthenium tetroxide/pyridine catalyst system have led us to examine ruthenium complexes with tunable ligands. The complex (Me3tacn)RuCl3 (Me3tacn = 1,4,7-trimethyl-1,4,7-triazacyclononane), in combination with silver perchlorate and ceric ammonium nitrate, catalyzes tertiary and benzylic C--H hydroxylation at room temperature with up to 80 turnovers. This catalyst system displays functional group compatibility and turnover numbers comparable with or superior to known catalysts for C--H hydroxylation. Mechanistic studies suggest that the reaction proceeds via hydrogen atom abstraction followed by fast, solvent-caged radical rebound. Efforts to tune the ligand to further increase turnover numbers and catalyst selectivity are described.
Book Synopsis The Design of Organic and Metal-based Catalysts for the Oxidative Functionalization of Aliphatic Carbon-hydrogen Bonds by : Benjamin Henry Brodsky
Download or read book The Design of Organic and Metal-based Catalysts for the Oxidative Functionalization of Aliphatic Carbon-hydrogen Bonds written by Benjamin Henry Brodsky and published by . This book was released on 2007 with total page 652 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis The Development of a Metal-free Catalytic Method for the Selective Hydroxylation of Aliphatic C-H Bonds by : Nichole Danielle Litvinas
Download or read book The Development of a Metal-free Catalytic Method for the Selective Hydroxylation of Aliphatic C-H Bonds written by Nichole Danielle Litvinas and published by . This book was released on 2010 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The diversity and structural intricacies of molecules needed for pharmaceutical, biological, and materials applications have challenged chemists to develop transformative chemical processes that greatly facilitate small molecule synthesis. C-H Bond functionalization represents one such class of reaction types, and is a general problem for reaction discovery that has witnessed an explosion of interest within the past 10 years. Inspired largely by Nature's ability to conduct site- and stereoselective C-H bond oxidation reactions, we have been driven to design small molecule catalysts that can emulate such processes. Our focus has taken aim at the problem of C-H bond hydroxylation, efforts that have yielded a novel, non-metal-based catalytic system for the selective oxidation of tertiary C-H bonds. These findings contrast the large body of literature detailing C-H hydroxylation reactions through transition-metal mediated catalysis. 1,2,3-Benzoxathiazine-2,2-dioxide-based heterocycles have been shown to function as catalysts for C-H hydroxylation with hydrogenperoxide operating as the terminal oxidant. The evolution of this catalytic process, which capitalizes on the unique reactivity of an oxaziridine intermediate, was made possible using density functional theory to help guide reagent design. In addition, kinetic analysis of the stoichiometric oxygen-atom transfer reaction has provided insight into the principal features that influence oxaziridine reactivity. This information coupled with the discovery that reactions could be conducted under aqueous reaction conditions with hydrogenperoxide has resulted in a markedly improved process for tertiary C-H hydroxylation. The reaction occurs stereospecifically and with predictable chemoselectivity in substrates possessing more than one tertiary C-H center. The enhanced performance of this catalytic process has been ascribed to the hydrophobic aggregation of the benzoxathiazinane catalyst and hydrocarbon substrate, which serves to accelerate the kinetically slow hydroxylation event.
Book Synopsis Activation and Functionalization of C-H Bonds by : Karen I. Goldberg
Download or read book Activation and Functionalization of C-H Bonds written by Karen I. Goldberg and published by ACS Symposium. This book was released on 2004 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Activation and Functionalization of C-H Bonds explores recent developments in the reaction chemistry of solution-phase transition-metal based systems with simple hydrocarbons and with more complex organic molecules. More than 20 internationally leading research groups contributed to this volume, and their chapters cover such topics as fundamental theoretical and mechanistic studies of C-H bond activation by metal complexes, catalytic systems for alkane functionalization, and new applications in synthetic organic chemistry. An introductory chapter offers an overview of stoichiometric and catalytic reactions of C-H bonds with transition metal complexes. The C-H bond is the most widespread linkage in organic chemistry, present in virtually every organic molecule. Unfortunately, C-H bonds are famously resistant to selective chemical transformations. The development of methods for their selective transformations has enormous potential value in fields ranging from the chemistry of fuels (for example, the conversion of methane to methanol) to the synthesis of the most complex organic molecules.
Book Synopsis C-H Activation for Asymmetric Synthesis by : Françoise Colobert
Download or read book C-H Activation for Asymmetric Synthesis written by Françoise Colobert and published by John Wiley & Sons. This book was released on 2019-11-11 with total page 294 pages. Available in PDF, EPUB and Kindle. Book excerpt: Provides, in one handbook, comprehensive coverage of one of the hottest topics in stereoselective chemistry Written by leading international authors in the field, this book introduces readers to C-H activation in asymmetric synthesis along with all of its facets. It presents stereoselective C-H functionalization with a broad coverage, from outer-sphere to inner-sphere C-H bond activation, and from the control of olefin geometry to the induction of point, planar and axial chirality. Moreover, methods wherein asymmetry is introduced either during the C-H activation or in a different elementary step are discussed. Presented in two parts?asymmetric activation of C(sp3)-H bonds and stereoselective synthesis implying activation of C(sp2)-H bonds?CH-Activation for Asymmetric Synthesis showcases the diversity of stereogenic elements, which can now be constructed by C-H activation methods. Chapters in Part 1 cover: C(sp3)-H bond insertion by metal carbenoids and nitrenoids; stereoselective C-C bond and C-N bond forming reactions through C(sp3)?H bond insertion of metal nitrenoids; enantioselective intra- and intermolecular couplings; and more. Part 2 looks at: C-H activation involved in stereodiscriminant step; planar chirality; diastereoselective formation of alkenes through C(sp2)?H bond activation; amongst other methods. -Covers one of the most rapidly developing fields in organic synthesis and catalysis -Clearly structured in two parts (activation of sp3- and activation of sp2-H bonds) -Edited by two leading experts in C-H activation in asymmetric synthesis CH-Activation for Asymmetric Synthesis will be of high interest to chemists in academia, as well as those in the pharmaceutical and agrochemical industry.
Book Synopsis Remote C-H Bond Functionalizations by : Debabrata Maiti
Download or read book Remote C-H Bond Functionalizations written by Debabrata Maiti and published by John Wiley & Sons. This book was released on 2021-04-26 with total page 450 pages. Available in PDF, EPUB and Kindle. Book excerpt: A guide to contemporary advancements in the field of distal C-H functionalizations An important and dynamic topic within the modern field of organic synthesis, selective functionalization of C-H bonds can be used in a variety of applications across the pharmaceutical and agrochemical industries. Remote C-H Bond Functionalizations presents an inclusive account of the most recent developments and potential applications of performing variegated functionalizations selectively at the distal positions of organic compounds. Featuring contributions by an international team of experts, this authoritative volume provides deep insight into distal functionalizations, including detailed discussion of mechanisms, the engineering of templates, and the design of strategies. The text covers a diverse range of topics including C-H functionalization of palladium/norbornene catalysis, ruthenium-catalyzed remote functionalization, the non-directed distal C(sp2)-H, functionalization, transition metal catalyzed distal para-selective C-H functionalization, and much more. Reviewing contemporary advancements in the field while laying the foundation for future research, this important resource: Provides the most recent research and thorough coverage of the subject available in a single volume Offers practical information on C-H functionalizations in various industries Includes an up-to-date introduction to distal C-H functionalizations Remote C-H Bond Functionalizations is a must-read for every synthetic chemist, including chemists working with organometallics, organic chemists and researchers, and industrial chemists.
Book Synopsis Organotransition Metal Chemistry: From Bonding to Catalysis by : John F. Hartwig
Download or read book Organotransition Metal Chemistry: From Bonding to Catalysis written by John F. Hartwig and published by . This book was released on 2010-02-10 with total page 1172 pages. Available in PDF, EPUB and Kindle. Book excerpt: Based on Collman et al.'s best-selling classic book, Principles and Applications of Organotransition Metal Chemistry, Hartwig's text consists of new or thoroughly updated and restructured chapters and provides an in-depth view into mechanism, reaction scope, and applications. It covers the most important developments in the field over the last twenty years with great clarity with a selective, but thorough and authoritative coverage of the fundamentals of organometallic chemistry, the elementary reactions of these complexes, and many catalytic processes occurring through organometallic intermediates, making this the Organotransition Metal Chemistry text for a new generation of scientists.
Book Synopsis Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds by : Lutz Ackermann
Download or read book Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds written by Lutz Ackermann and published by John Wiley & Sons. This book was released on 2017-10-10 with total page 417 pages. Available in PDF, EPUB and Kindle. Book excerpt: Filling a gap in the literature, this book comprehensively reviews catalytic C-H addition reactions of (hetero)aromatic hydrocarbons across carbon-carbon multiple bonds. In so doing, it summarizes both the scope as well as the limitations of different catalyst systems and building blocks, while highlighting their application to the synthesis of pharmaceuticals as well as commodity chemicals. Focusing on the latest developments, the team of authors comprising leaders in the field covers such topics as the hydroarylation of olefins, alkyne hydroarylation in the presence of transition metal catalysts, reaction of alkynes with arylboronic acids, and allene hydroarylation, as well as the synthesis of functionalized arenes and heteroaromatics. A must-have for synthetic chemists in academia and industry dealing with catalysis, organometallic chemistry, the synthesis of natural products, fine chemicals, pharmaceuticals, products of the chemical industry and organic materials.
Book Synopsis Natural Product Biosynthesis by : Christopher T. Walsh
Download or read book Natural Product Biosynthesis written by Christopher T. Walsh and published by Royal Society of Chemistry. This book was released on 2017-04-28 with total page 787 pages. Available in PDF, EPUB and Kindle. Book excerpt: This textbook describes the types of natural products, the biosynthetic pathways that enable the production of these molecules, and an update on the discovery of novel products in the post-genomic era.
Author :Paul R. Ortiz de Montellano Publisher :Springer Science & Business Media ISBN 13 :0387274472 Total Pages :702 pages Book Rating :4.3/5 (872 download)
Book Synopsis Cytochrome P450 by : Paul R. Ortiz de Montellano
Download or read book Cytochrome P450 written by Paul R. Ortiz de Montellano and published by Springer Science & Business Media. This book was released on 2007-02-05 with total page 702 pages. Available in PDF, EPUB and Kindle. Book excerpt: Cytochrome P450: Structure, Mechanism, and Biochemistry, third edition is a revision of a review that summarizes the current state of research in the field of drug metabolism. The emphasis is on structure, mechanism, biochemistry, and regulation. Coverage is interdisciplinary, ranging from bioinorganic chemistry of cytochrome P450 to its relevance in human medicine. Each chapter provides an in-depth review of a given topic, but concentrates on advances of the last 10 years.
Book Synopsis Development of Catalytic Metal-mediated C--H Hydroxylation Methods with Improved Functional Group Compatibility by : James Booker Christianson Mack
Download or read book Development of Catalytic Metal-mediated C--H Hydroxylation Methods with Improved Functional Group Compatibility written by James Booker Christianson Mack and published by . This book was released on 2018 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Catalytic C--H hydroxylation methods constitute an enabling technology for the synthesis and structural diversification of organic molecules. Current methods are challenged by substrates that are densely functionalized and contain cross-reactive groups. In recent efforts to address such issues, we have developed two catalytic systems that advance the capability of chemists to functionalize highly complex molecules. Nitrogen-derived functional groups and N-heterocycles are ubiquitous in active pharmaceutical ingredients (APIs) and natural products, but are incompatible with most current chemical methods for oxidation. We describe the development of a new protocol for sp3-C--H hydroxylation. The reaction is performed in aqueous acid with catalytic cis-[Ru(dtbpy)2Cl2] (dtbpy = 4,4'-di-tert-butyl(2,2'-bipyridine)) and enables oxidation of structurally diverse amine- and heterocycle-containing molecules. Tertiary and benzylic C--H hydroxylation is strongly favored over N-oxidation in amine-derived and N-heterocyclic substrates. In efforts to further develop this technology, a multi-pronged mechanistic study was undertaken using techniques such as pressurized sample infusion high-resolution mass spectrometry (PSI-HRMS), 19F NMR spectroscopy, electrochemistry, and reaction kinetics analysis. This work has afforded insight into ligand structure-activity relationships and the identity of relevant active catalytic species. Turnover numbers (TONs) of a series of catalysts examined are strongly correlated to the rate and extent of ligand dissociation that occurs under the reaction conditions. Insights gained from these studies should give way to the design of next-generation catalysts for efficient C--H oxidation of complex molecules. In related studies, we describe the development of a Mn-catalyzed hydroxylation reaction that uses H2O2 or peracetic acid as the bulk oxidant. This method complements our Ru-based chemistry by enabling the functionalization of stronger, less reactive C--H bonds. The protocol features exceptionally low catalyst loadings, accommodates a variety of simple ligands (including 2,2'-bipyridine), and favors 2o alcohol products over the corresponding ketone derivatives. Preliminary studies aimed at understanding catalyst degradation/arrest mechanisms are also described.
Book Synopsis Iron Catalysis in Organic Chemistry by : Bernd Plietker
Download or read book Iron Catalysis in Organic Chemistry written by Bernd Plietker and published by John Wiley & Sons. This book was released on 2008-09-08 with total page 295 pages. Available in PDF, EPUB and Kindle. Book excerpt: This first comprehensive book to cover this exciting field also deals with the biological aspects, such as enzymes with iron. Following an introduction, this handy reference and handbook goes on to deal with reductions, oxidations of C, H- and C=C bonds, oxidative allylic oxygenation and amination, the oxidation of heteroatoms, cross coupling reactions, aromatic and nucleophilic substitutions, addition to carbonyl compounds, and cyclisations as well as ring opening reactions. The chapters are clearly classified according to the reaction type, allowing readers to quickly locate the desired information.
Book Synopsis Solvents as Reagents in Organic Synthesis by : Xiao-Feng Wu
Download or read book Solvents as Reagents in Organic Synthesis written by Xiao-Feng Wu and published by John Wiley & Sons. This book was released on 2018-01-03 with total page 552 pages. Available in PDF, EPUB and Kindle. Book excerpt: Written by highly renowned and experienced authors, this is the only reference on the application of solvents as reagents. Clearly structured, the text describes various methods for the activation and reaction of these small molecules, highlighting the synthetic opportunities as well as process-oriented advantages. To this end, all relevant types of solvents are covered separately and emphasized with numerous synthetic examples, while taking care to explain applications so as to avoid undesired side reactions. The result is a unique resource for every synthetic chemist and reaction engineer in industry and academia working on the methodical optimization of synthetic transformations.
Book Synopsis Modern Organic Synthesis by : George S. Zweifel
Download or read book Modern Organic Synthesis written by George S. Zweifel and published by John Wiley & Sons. This book was released on 2017-03-13 with total page 416 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book bridges the gap between sophomore and advanced / graduate level organic chemistry courses, providing students with a necessary background to begin research in either an industry or academic environment. • Covers key concepts that include retrosynthesis, conformational analysis, and functional group transformations as well as presents the latest developments in organometallic chemistry and C–C bond formation • Uses a concise and easy-to-read style, with many illustrated examples • Updates material, examples, and references from the first edition • Adds coverage of organocatalysts and organometallic reagents
Book Synopsis Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes by : A.E. Shilov
Download or read book Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes written by A.E. Shilov and published by Springer Science & Business Media. This book was released on 2001-11-30 with total page 556 pages. Available in PDF, EPUB and Kindle. Book excerpt: hemistry is the science about breaking and forming of bonds between atoms. One of the most important processes for organic chemistry is breaking bonds C–H, as well as C–C in various compounds, and primarily, in hydrocarbons. Among hydrocarbons, saturated hydrocarbons, alkanes (methane, ethane, propane, hexane etc. ), are especially attractive as substrates for chemical transformations. This is because, on the one hand, alkanes are the main constituents of oil and natural gas, and consequently are the principal feedstocks for chemical industry. On the other hand, these substances are known to be the less reactive organic compounds. Saturated hydrocarbons may be called the “noble gases of organic chemistry” and, if so, the first representative of their family – methane – may be compared with extremely inert helium. As in all comparisons, this parallel between noble gases and alkanes is not fully accurate. Indeed the transformations of alkanes, including methane, have been known for a long time. These reactions involve the interaction with molecular oxygen from air (burning – the main source of energy!), as well as some mutual interconversions of saturated and unsaturated hydrocarbons. However, all these transformations occur at elevated temperatures (higher than 300–500 °C) and are usually characterized by a lack of selectivity. The conversion of alkanes into carbon dioxide and water during burning is an extremely valuable process – but not from a chemist viewpoint.
Download or read book Iron Catalysis written by Bernd Plietker and published by Springer Science & Business Media. This book was released on 2011-01-05 with total page 227 pages. Available in PDF, EPUB and Kindle. Book excerpt: Juan I. Padrón and Víctor S. Martín: Catalysis by means of Fe-based Lewis acids; Hiroshi Nakazawa*, Masumi Itazaki: Fe–H Complexes in Catalysis; Kristin Schröder, Kathrin Junge, Bianca Bitterlich, and Matthias Beller: Fe-catalyzed Oxidation Reactions of Olefins, Alkanes and Alcohols: Involvement of Oxo- and Peroxo Complexes; Chi-Ming Che, Cong-Ying Zhou, Ella Lai-Ming Wong: Catalysis by Fe=X Complexes (X=NR, CR2); René Peters, Daniel F. Fischer and Sascha Jautze: Ferrocene and Half Sandwich Complexes as Catalysts with Iron Participation; Markus Jegelka, Bernd Plietker: Catalysis by Means of Complex Ferrates.
