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Transition Metal Catalyzed Asymmetric Hydrocarbonylation Of Functionalized Alkenes
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Book Synopsis Transition Metal Catalyzed Asymmetric Hydrocarbonylation of Functionalized Alkenes by : Karen Totland
Download or read book Transition Metal Catalyzed Asymmetric Hydrocarbonylation of Functionalized Alkenes written by Karen Totland and published by . This book was released on 1993 with total page 260 pages. Available in PDF, EPUB and Kindle. Book excerpt: Aromatic and aliphatic vinyl sulfones and sulfoxides have been hydroformylated with CO/H$\sb2$ in the presence of the zwitterionic rhodium complex, 1,5-cyclooctadiene rhodium(I) tetraphenylborate, (1,5-(COD)Rh$\sp+(\eta\sp6$-$\rm C\sb6H\sb5)B(C\sb6H\sb5)\sb{3\sp-}),$ to give previously unknown aldehydic sulfones and sulfoxides in excellent yields and regioselectivities. The hydroformylation of phenyl vinyl sulfoxide in the presence of 1,5-(COD)Rh$\sp+(\eta\sp6$-$\rm C\sb6H\sb5)B(C\sb6H\sb5)\sb{3\sp-}$ and the chiral phosphine ligand, BINAP, demonstrated considerable stereodifferentiating ability (up to 50% de). The hydroesterification of vinyl esters with CO/MeOH/bis(triphenylphosphine)palladium(II) dichloride, $\rm ((PPh\sb3)\sb2PdCl\sb2),$ has been studied. The critical necessity of catalytic amounts of acid, such as $\rm H\sb3PO\sb4$ (1 mol% relative to substrate), was revealed. This reaction is also catalyzed by the cationic palladium(II) hydrido complex, $\rm \lbrack (Cy\sb3P)\sb2Pd(H)(H\sb2O)\rbrack\sp+BF\sb{4\sp-}.$ Lactic acid derivatives can be synthesized with modest ee's (up to 30%) using $\rm \lbrack (Cy\sb3P)\sb2Pd(H)(H\sb2O)\rbrack\sp+BF\sb{4\sp-}$ in the presence of BINAP. Design and synthesis of new chiral borate ligands and their rhodium complexes have been undertaken.
Book Synopsis Earth-Abundant Transition Metal Catalyzed Reactions by :
Download or read book Earth-Abundant Transition Metal Catalyzed Reactions written by and published by Elsevier. This book was released on 2024-09-18 with total page 270 pages. Available in PDF, EPUB and Kindle. Book excerpt: Earth-Abundant Transition Metal Catalyzed Reactions, Volume 74 in the Advances in Catalysis series, highlights new advances in the field, with this new volume presenting interesting chapters. Each chapter is written by an international board of authors. Chapters in this new release include in Chiral Iron Complexes for Asymmetric Catalysis, Recent advances in Ni-catalyzed Functionalization of Strong C-O and C-H Bonds, Low-valent Molecular Cobalt Complexes for Reductive Chemistry, Iron-catalyzed group-transfer reactions with hypervalent iodine reagents, and Iron Porphyrins for Mediating Atom Efficient C–C Bond Formations. Provides the authority and expertise of leading contributors from an international board of authors Presents the latest release in Advances in Catalysis serials Updated release includes the latest information in the field
Book Synopsis Metal-Catalyzed Asymmetric Hydrogenation. Evolution and Prospect by :
Download or read book Metal-Catalyzed Asymmetric Hydrogenation. Evolution and Prospect written by and published by Academic Press. This book was released on 2021-11-23 with total page 438 pages. Available in PDF, EPUB and Kindle. Book excerpt: Metal-Catalyzed Asymmetric Hydrogenation, Volume 68 in the Advances in Catalysis series, fills the gap between journal papers and textbooks across diverse areas of catalysis research. For more than 60 years, this series has recorded and presented the latest progress in the field of catalysis, giving the scientific community comprehensive and authoritative reviews. Chapters in this new release include Asymmetric hydrogenation of functionalized olefins, Asymmetric hydrogenation of unfunctionalized olefins or with poorly coordinative groups, Asymmetric hydrogenation of imines, Asymmetric hydrogenation of ketones, Asymmetric hydrogenation in industry, and Computational insights into metal-catalyzed asymmetric hydrogenation. This series is an invaluable and comprehensive resource for chemical engineers and chemists working in the field of catalysis in both academia and industry, with this release focusing on solid acids, surface acidity and heterogeneous acid catalysis. Contains authoritative reviews written by experts in the field Explores topics that reflect progress in the field, such as catalyst synthesis, catalyst characterization, catalytic chemistry, reaction engineering, computational chemistry and physics Provides insightful and critical articles that are fully edited to suit various backgrounds
Book Synopsis Transition Metal-catalyzed Functionalization of Carbon-hydrogen Bonds in Alkenes by : Xiaolin Qian
Download or read book Transition Metal-catalyzed Functionalization of Carbon-hydrogen Bonds in Alkenes written by Xiaolin Qian and published by . This book was released on 2023 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Alkenes can undergo a variety of chemical reactions to form more complex molecules with a range of functional groups. This makes them useful starting materials for synthesizing a wide range of organic compounds. Chapter I provided an overview of the development history of alkenyl C8́2H bond activation. The early reactions of C8́2H compounds with metal complexes, as well as stoichiometric activation of the transition metal-activated C-H bond, were discussed. Then the first successful and efficient organometallic-catalyzed transformations of a C8́2H bond, the first transition metal-catalyzed vinylic C-H functionalization, and the first transition metal-catalyzed olefinic C-H functionalization under mild conditions were demonstrated. Finally, enantioselective vinylic C-H functionalization was discussed. In Chapter II, a method for enantioselective vinylic C(sp2)8́2H bond activation using a Ru(II) catalyst and a chiral transient directing group was developed. Chiral amine was also utilized to control the Z/E stereoselectivity. The method demonstrated a broad substrate scope with good yield, high Z/E ratio stereoselectivity, and excellent enantioselectivity. Its synthetic utility was demonstrated by the synthesis of key structural motifs of particularly useful natural products and pharmaceutical compounds. Additionally, a rare vinylic C8́2H bond activated ruthenic complex was isolated and determined by single-crystal X-ray diffraction. The methodology suggested in this work is expected to facilitate the further development of asymmetric vinylic C8́2H functionalization reactions. In Chapter III, a practical and efficient methodology for Ru(II)-catalyzed enantioselective alkenyl C-H bond functionalization of indole-substituted acrylaldehyde derivatives via the chiral transient directing group (CTDG) strategy to obtain optically active pyrrolo[1,2-a]indole derivatives was suggested. The methodology resulted in a series of optically active products with good yields (up to 80%), good stereoselectivity (up to 25.0:1 Z/E), and excellent enantioselectivity (up to 95% ee). Furthermore, synthetic transformations were explored. Chapter IV presented the first demonstration of a sequentially composed catalytic substitution reaction of alkenes for building multi-amido methylated derivatives while reserving the Ï0- components. The process involved a simple Fe (III)-catalyst and bisamidomethane reagent, which directly and selectively transformed Îł-substituted styrenes into several biologically and pharmaceutically relevant N-heterocycles through tandem processes.
Book Synopsis Asymmetric Catalysis from a Chinese Perspective by : Shengming Ma
Download or read book Asymmetric Catalysis from a Chinese Perspective written by Shengming Ma and published by Springer Science & Business Media. This book was released on 2011-07-06 with total page 368 pages. Available in PDF, EPUB and Kindle. Book excerpt: Qi-Lin Zhou and Jian-Hua Xie: Chiral Spiro Catalysts.- Fuk Loi Lam, Fuk Yee Kwong and Albert S. C. Chan: Chiral Phosphorus Ligands with Interesting Properties and Practical Applications.- Jiang Pan, Hui-Lei Yu, Jian-He Xu, Guo-Qiang Lin: Advances in Biocatalysis: Enzymatic Reactions and Their Applications.- Mei-Xiang Wang: Enantioselective Biotransformations of Nitriles.- Man Kin Wong, Yiu Chung Yip and Dan Yang: Asymmetric Epoxidation Catalyzed by Chiral Ketones.- W. J. Liu, N. Li and L. Z. Gong: Asymmetric Organocatalysis.- Qing-Hua Fan and Kuiling Ding: Enantioselective Catalysis with Structurally Tunable Immobilized Catalysts.- Chang-Hua Ding, Xue-Long Hou: Transition Metal-Catalyzed Asymmetric Allylation.- Jian Zhou and Yong Tang: Enantioselective Reactions with Trisoxazolines.- Xiang-Ping Hu, Duo-Sheng Wang, Chang-Bin Yu, Yong-Gui Zhou, and Zhuo Zheng: Adventure in Asymmetric Hydrogenation: Synthesis of Chiral Phosphorus Ligands and Asymmetric Hydrogenation of Heteroaromtics.
Book Synopsis Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis by : Uli Kazmaier
Download or read book Transition Metal Catalyzed Enantioselective Allylic Substitution in Organic Synthesis written by Uli Kazmaier and published by Springer Science & Business Media. This book was released on 2011-10-29 with total page 354 pages. Available in PDF, EPUB and Kindle. Book excerpt: Giovanni Poli, Guillaume Prestat, Frédéric Liron, Claire Kammerer-Pentier: Selectivity in Palladium Catalyzed Allylic Substitution.- Jonatan Kleimark and Per-Ola Norrby: Computational Insights into Palladium-mediated Allylic Substitution Reactions.- Ludovic Milhau, Patrick J. Guiry: Palladium-catalyzed enantioselective allylic substitution.- Wen-Bo Liu, Ji-Bao Xia, Shu-Li You: Iridium-Catalyzed Asymmetric Allylic Substitutions.- Christina Moberg: Molybdenum- and Tungsten-Catalyzed Enantioselective Allylic Substitutions.- Jean-Baptiste Langlois, Alexandre Alexakis: Copper-catalyzed enantioselective allylic substitution.- Jeanne-Marie Begouin, Johannes E. M. N. Klein, Daniel Weickmann, B. Plietker: Allylic Substitutions Catalyzed by Miscellaneous Metals.- Barry M. Trost, Matthew L. Crawley: Enantioselective Allylic Substitutions in Natural Product Synthesis.
Download or read book Part 1 written by Derek Schipper and published by . This book was released on 2011 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Part 1: Transition-metal-catalyzed direct transformations of aromatic C-H bonds are emerging as valuable tools in organic synthesis. These reactions are attractive because of they allow for inherently efficient construction of organic building blocks by minimizing the pre-activation of substrates. Of these processes, direct arylation has recently received much attention due to the importance of the biaryl core in medicinal and materials chemistry. Also, alkyne hydroarylation has garnered interest because it allows for the atom-economical synthesis of functionalized alkenes directly from simple arenes and alkynes. Described in this thesis are number of advancements in these areas. First, palladium catalyzed direct arylation of azine N-oxides using synthetically important aryl triflates is described. Interesting reactivity of aryl triflates compared to aryl bromides was uncovered and exploited in the synthesis of a compound that exhibits antimalarial and antimicrobial activity. Also reported is the efficient, direct arylation enabled (formal) synthesis of six thiophene based organic electronic materials in high yields using simple starting materials. Additionally, the site-selective direct arylation of both sp2 and sp3 sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner and is applied to the synthesis of the natural products, Papaverine and Crykonisine. Mechanistic investigations point towards the intimate involvement of the base in the mechanism of these reactions. Next, the rhodium(III)-catalyzed hydroarylation of internal alkynes is described. Good yields are obtained for a variety of alkynes and arenes with excellent regioselectivity for unsymmetrically substituted alkynes. Mechanistic investigations suggest that this reaction proceeds through arene metalation with the cationic rhodium catalyst, which enables challenging intermolecular reactivity. Part 2: Access to single enantiomer compounds is a fundamental goal in organic chemistry and despite remarkable advances in enantioselective synthesis, their preparation remains a challenge. Kinetic resolution of racemic products is an important method to access enantioenriched compounds, especially when alternative methods are scarce. Described in this thesis is the resolution of tertiary and secondary alcohols, which arise from ketone and aldehyde aldol additions. The method is technically simple, easily scalable, and provides tertiary and secondary alcohols in high enantiomeric ratios. A rationale for the unique reactivity/selectivity associated with (1S,2R)-N-methylephedrine in the resolution is proposed. Organocatalysis is a rapidly developing, powerful field for the construction of enantioenriched organic molecules. Described here is a complimentary class of organocatalysis using simple aldehydes as temporary tethers to perform challenging formally intermolecular reactions at room temperature. This strategy allows for the enantioselective, intermolecular cope-type hydroamination of allylic amines with hydroxyl amines. Also, interesting catalytic reactivity for dichloromethane is revealed.
Book Synopsis Hydrofunctionalization by : Valentine P. Ananikov
Download or read book Hydrofunctionalization written by Valentine P. Ananikov and published by Springer. This book was released on 2012-09-29 with total page 377 pages. Available in PDF, EPUB and Kindle. Book excerpt: Valentine P. Ananikov, Irina P. Beletskaya: Alkyne and alkene insertion into metal-heteroatom and metal-hydrogen bonds – the key stages of hydrofunctionalization process.- Akihiko Ishii* and Norio Nakata: The Mechanism for Transition Metal-Catalyzed Hydrochalcogenation of Unsaturated Organic Molecules.- A. L. Reznichenko and Kai C. Hultzsch: Early Transition Metal (Group 3-5, Lanthanides and Actinides) and Main Group Metal (Group 1, 2, and 13) Catalyzed Hydroamination.- Naoko Nishina and Yoshinori Yamamoto: Late transition metal catalyzed hydroamination.- Sumod A. Pullarkat and Pak-Hing Leung: Chiral Metal Complex Promoted Asymmetric Hydrophosphinations.- Masato Tanaka: Recent Progress in Transition Metal-Catalyzed Addition Reactions of H-P(O) Compounds with Unsaturated Carbon Linkages.- Christian Bruneau: Group 8 metals-catalyzed O-H bond addition to unsaturated molecules.- Giorgio Abbiati, Egle M. Beccalli, Elisabetta Rossi: Groups 9 and 10 metals-catalyzed O-H bond addition to unsaturated molecules.- Núria Huguet and Antonio M. Echavarren: Gold-Catalyzed O-H Bond Addition to Unsaturated Organic Molecules.- Akiya Ogawa: Transition-Metal-Catalyzed S-H and Se-H Bonds Addition to Unsaturated Molecules.
Book Synopsis Transition Metal Catalyzed Enantioselective Hydroboration and Hydrovinylation of Alkenes by : Krishnaja Duvvuri
Download or read book Transition Metal Catalyzed Enantioselective Hydroboration and Hydrovinylation of Alkenes written by Krishnaja Duvvuri and published by . This book was released on 2018 with total page 500 pages. Available in PDF, EPUB and Kindle. Book excerpt: Economic methods to stitch feedstocks onto molecules using chemical synthesis can greatly impact the design and manufacture of molecules, from medicine to materials. For example, olefins, one of the most abundantly obtained class of feedstocks from the petroleum refining industry, are starting carbon units for many of the processes used to produce value-added chemicals in the pharmaceutical, agrochemical and polymer industry. However, many of these processes are often limited with harsh reaction conditions, poor yields and low selectivities. Organic chemists have long been trying to address the unmet challenges in this field; to simultaneously activate and functionalize olefins under mild reaction conditions, with the desired level of precision and selectivity, bond-by-bond, in order to access high value-added molecules from cheap and abundant lower alkenes. My graduate research work focusses on developing methods to address the challenges in olefin activation by employing transition metal catalysts as powerful tools. Mimicking nature’s enzymes and its extra-ordinary selectivity, we seek to address olefin functionalization, more specifically carbon-boron and carbon-carbon bond forming reactions, which could provide a powerful means to access a broad range of advanced, highly functionalized target molecules of interest to medicinal chemistry and related areas. We seek to develop a highly efficient catalytic protocol using the earth abundant metal, cobalt, linked to suitable ligands, to achieve the hydroboration of unactivated olefins to obtain organo-borane products with desired level of yield and selectivity. Although these are highly versatile compounds having wide synthetic utility as pharmaceutical intermediates, there is a paucity of methods to make organo-boranes directly from feedstocks. In this research methodology, a systematic investigation of diverse classes of ligand-cobalt complexes was performed to activate unactivated olefins. Based on mechanistic insights and experimental observations, the ligands were optimized to get the best selectivity of the desired value-added products from substituted dienes. The parameters effecting yields such as organic solvents, temperature and catalyst loading were also examined to process the best yields. The operationally simple, yet unprecedented reactions we discovered expand the realm of hydrofunctionalizations to provide direct access to a number of boranes, of interest in organic synthesis. The resulting boron compounds were further transformed into several chiral building blocks, thus expanding the scope of the primary process for advanced synthesis. -aryl--aminobutyric acid (GABA) derivatives are a large class of medicinally active compounds, examples of which include (R)-Baclophen and (R)-Rolipram. Methods for the efficient enantioselective synthesis this class of compounds were explored through the asymmetric hydrovinylation reaction, the addition of ethylene to olefins. By employing finely tuned chiral nickel complexes, several -substituted styrenes of relevance were found to undergo hydrovinylation in good to modest enantioselectivites. Model subtstrates were further transformed into the GABA precursor illustrating that this class of medicinally active compounds can be accessed from simple starting materials using the hydrovinylation reaction. We expect that the discoveries like this will shorten the considerable distance between the conceptualization of a molecule as a drug candidate and its large-scale synthesis. Beyond this transformation we anticipate that this reactivity will inspire further advances in olefin functionalization.
Book Synopsis Transition Metal Catalyzed Ring-opening Reactions of Unsymmetrical Oxabicyclic Alkenes by : Raheem Mohammed Abdul
Download or read book Transition Metal Catalyzed Ring-opening Reactions of Unsymmetrical Oxabicyclic Alkenes written by Raheem Mohammed Abdul and published by . This book was released on 2013 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Heterocycles from Transition Metal Catalysis by : András Kotschy
Download or read book Heterocycles from Transition Metal Catalysis written by András Kotschy and published by Springer Science & Business Media. This book was released on 2005-09-30 with total page 224 pages. Available in PDF, EPUB and Kindle. Book excerpt: "Heterocycles from Transition Metal Catalysis: Formation and Functionalization" provides a concise summary of the prominent role of late transition metal (palladium, nickel, copper) catalysed processes in the synthesis and functionalization of heterocyclic systems. It gives an introduction to catalytic transformations, an overview of the most important reaction types, and presents synthetically useful catalytic processes classified by the target system and the type of transformation. The book provides a representative selection of transition metal catalysed reactions transformations that are relevant in heterocyclic chemistry. In this way, the authors present a useful resource for members of the academic community looking for a textbook as well as industrial chemists in search of a reference book. This book will be an invaluable resource for synthetic chemists, medicinal chemists, and those more generally interested in applied catalysis.
Book Synopsis Transition Metal Catalyzed Carbonylative Synthesis of Heterocycles by : Xiao-Feng Wu
Download or read book Transition Metal Catalyzed Carbonylative Synthesis of Heterocycles written by Xiao-Feng Wu and published by Springer. This book was released on 2015-12-14 with total page 176 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field. All chapters from Topics in Heterocyclic Chemistry are published Online First with an individual DOI. In references, Topics in Heterocyclic Chemistry is abbreviated as Top Heterocycl Chem and cited as a journal.
Book Synopsis Transition Metal Catalyzed Polymerizations by : Roderic P. Quirk
Download or read book Transition Metal Catalyzed Polymerizations written by Roderic P. Quirk and published by Taylor & Francis. This book was released on 1983 with total page 478 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Transition Metal Catalysed Reactions by : International Union of Pure and Applied Chemistry
Download or read book Transition Metal Catalysed Reactions written by International Union of Pure and Applied Chemistry and published by . This book was released on 1999 with total page 524 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Homogeneous Transition Metal Catalyzed Reactions by : William R. Moser
Download or read book Homogeneous Transition Metal Catalyzed Reactions written by William R. Moser and published by . This book was released on 1992 with total page 648 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Transition Metal-Catalyzed C-H Functionalization for Sustainable Syntheses of Alkenes and Heterocycles by : Wenbo Ma
Download or read book Transition Metal-Catalyzed C-H Functionalization for Sustainable Syntheses of Alkenes and Heterocycles written by Wenbo Ma and published by . This book was released on 2015 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Theoretical Aspects of Transition Metal Catalysis by : Gernot Frenking
Download or read book Theoretical Aspects of Transition Metal Catalysis written by Gernot Frenking and published by Springer Science & Business Media. This book was released on 2005-06-23 with total page 284 pages. Available in PDF, EPUB and Kindle. Book excerpt: Transition metal catalysis belongs to the most important chemical research areas because a ubiquitous number of chemical reactions are catalyzed by transition metal compounds. Many efforts are being made by industry and academia to find new and more efficient catalysts for chemical processes. Transition metals play a prominent role in catalytic research because they have been proven to show an enormous diversity in lowering the activation barrier for chemical reactions. For many years, the search for new catalysts was carried out by trial and error, which was costly and time consuming. The understanding of the mechanism of the catalytic process is often not very advanced because it is difficult to study the elementary steps of the catalysis with experimental techniques. The development of modern quantum chemical methods for calculating possible intermediates and transition states was a breakthrough in gaining an understanding of the reaction pathways of transition metal catalyzed reactions. This volume, organized into eight chapters written by leading scientists in the field, illustrates the progress made during the last decade. The reader will obtain a deep insight into the present state of quantum chemical research in transition metal catalysis.
