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New Transformations In The Transition Metal Catalyzed Hydrofunctionalization Of Alkynes
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Book Synopsis New Transformations in the Transition-metal Catalyzed Hydrofunctionalization of Alkynes by : Megan Armstrong
Download or read book New Transformations in the Transition-metal Catalyzed Hydrofunctionalization of Alkynes written by Megan Armstrong and published by . This book was released on 2021 with total page 185 pages. Available in PDF, EPUB and Kindle. Book excerpt: Hydrofunctionalization reactions are very useful transformations of unsaturated compounds and their development has been a major focus of research in the field of transition metal catalysis. These reactions allow the rapid build up of molecular complexity of simple substrates in a single transformation and recently significant progress has been made in the development of regio-, stereo- and enantioselective hydrofunctionalizations. Here we describe the development of three reactions involving transition metal-catalyzed hydrofunctionalization. The first is the hydroallylation of alkynes furnishing skipped dienes. Regioselective hydroallylation of nonsymmetrical internal alkynes was achieved through the installation of polar functional group in the propargylic position. This resulted in inductive polarization of the alkyne bond allowed for the regioselective synthesis of trisubstituted alkenes. The second reaction described is the diastereodivergent hydroarylation of alkynes. Both Z- and E-styrenes are accessed from one set of starting materials using synergistic Cu/Pd catalysis. The reaction proceeds through tandem Sonogashira cross-coupling followed by Z-selective semireduction and isomerization, where the diastereoselectivity is determined by the stoichiometry of a methanol additive. The last reaction describes the reductive three-component coupling of terminal alkynes, aryl halides and pinacolborane using synergistic Cu/Pd catalysis. Copper-catalyzed hydroboration followed by hydrocupration generates a key heterobimetallic complex, subsequent palladium-catalyzed cross-coupling with aryl halides provides benzylic alkyl boronates. Investigation of other electrophiles and enantioselective variants is currently underway.
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 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 New Transformations for the Synthesis of Highly Functionalized Organic Frameworks by : 蘇凱爾
Download or read book Transition Metal Catalyzed New Transformations for the Synthesis of Highly Functionalized Organic Frameworks written by 蘇凱爾 and published by . This book was released on 2019 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Modern Alkyne Chemistry by : Barry M. Trost
Download or read book Modern Alkyne Chemistry written by Barry M. Trost and published by John Wiley & Sons. This book was released on 2015-02-09 with total page 420 pages. Available in PDF, EPUB and Kindle. Book excerpt: A comprehensive and up-to-date overview of alkyne chemistry, taking into account the progress made over the last two decades. The experienced editors are renowned world leaders in the field, while the list of contributors reads like a "Who's Who" of synthetic organic chemistry. The result is a valuable reference not only for organic chemists at universities and in the chemical industry, but also for biologists and material scientists involved in the modern synthesis of organic compounds and materials.
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 Metal Catalyzed Cascade Reactions by : Thomas J.J. Müller
Download or read book Metal Catalyzed Cascade Reactions written by Thomas J.J. Müller and published by Springer. This book was released on 2010-11-18 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book highlights cyclization via carbopalladation and acylpalladation and Heck-pericyclic sequences. They discuss p-allyl palladium-based cascade reactions, Michael-type additions as an entry to transition-metal-promoted cyclizative transformations, and sequential or consecutive palladium-catalyzed processes, and show Pauson-Khand cascades, metal-catalyzed cyclizations of acyclic precursors, as well as cascade and sequential ruthenium-catalyzed transformations. This is a comprehensive overview of an exciting and highly dynamic, and innovative methodological concept.
Book Synopsis Transition Metal-Catalyzed Alkynylation Reactions by : Carmen Najera
Download or read book Transition Metal-Catalyzed Alkynylation Reactions written by Carmen Najera and published by CRC Press. This book was released on 2010-12-15 with total page 350 pages. Available in PDF, EPUB and Kindle. Book excerpt: New methods for performing alkynylation reactions are rapidly development. This book deals with the synthesis of internal alkynes employing transition-metal catalysis. In particular, it presents cross-coupling reactions leading to conjugated alkynes, including diarylated alkynes, enynes, and polynes. The text explores the wide range of applications for these types of systems, such as conducting polymers and nanostructures for material science, as well as the presence of these systems in pharmacologically interesting natural and synthetic products. In addition, the author explains why these alkynes are important starting materials for the preparation of other systems like carbocycles.
Book Synopsis Electrochemical-induced hydrofunctionalizations of alkenes and alkynes by : Yahui Zhang
Download or read book Electrochemical-induced hydrofunctionalizations of alkenes and alkynes written by Yahui Zhang and published by OAE Publishing Inc.. This book was released on 2024-03-01 with total page 29 pages. Available in PDF, EPUB and Kindle. Book excerpt: The hydrofunctionalizations of readily available alkenes and alkynes are one of the most effective and useful routes to afford diverse value-added compounds. Although traditional hydrofunctionalization strategies catalyzed by metal catalysts present convenient approaches, they are also accompanied by resource consumption and environmental crisis. Electrosynthesis, as a renewable and sustainable technology, has become a cost- and atom-efficient and useful synthetic route. In this review, the electrochemical-induced hydrofunctionalizations of alkenes and alkynes are summarized and presented. In each section, the electrochemical synthetic strategy to access hydrogenation and other hydrofunctionalization (hydroboration, hydrosilylation, hydroalkylation, hydroalkoxylation, hydrocyanation, hydrocarboxylation, etc.) products are elaborated in detail separately. Finally, the current challenges and prospects for electrochemical hydrofunctionalizations of unsaturated carbon‒carbon (C‒C) bonds are also discussed briefly.
Book Synopsis The Transition Metal Catalyzed New Organic Transformation of Enynes for Synthesis of Highly Functionalized Carbocyclic & Heterocyclic Systems by : 薩加
Download or read book The Transition Metal Catalyzed New Organic Transformation of Enynes for Synthesis of Highly Functionalized Carbocyclic & Heterocyclic Systems written by 薩加 and published by . This book was released on 2014 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Transition Metal Catalyzed Reactions and Functionalized Group Transformations by : Peng Wen Tan
Download or read book Transition Metal Catalyzed Reactions and Functionalized Group Transformations written by Peng Wen Tan and published by . This book was released on 2017 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Transition Metal Catalyzed Functionalization of Alkynes by : Avijit Hazra
Download or read book Transition Metal Catalyzed Functionalization of Alkynes written by Avijit Hazra and published by . This book was released on 2021 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Transition Metal-catalyzed Preparation and Functionalization of Nitrogen-containing Heterocycles by : Malcolm P. Huestis
Download or read book Transition Metal-catalyzed Preparation and Functionalization of Nitrogen-containing Heterocycles written by Malcolm P. Huestis and published by . This book was released on 2009 with total page 148 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Exploring Oxygenated Compounds for Efficient Transition Metal-catalyzed Molecular Transformations by : Xi-Jie Dai
Download or read book Exploring Oxygenated Compounds for Efficient Transition Metal-catalyzed Molecular Transformations written by Xi-Jie Dai and published by . This book was released on 2017 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: "This thesis advances the knowledge in two fundamentally important organic chemical transformations: (1) cleavage of carbon-oxygen bonds and (2) formation of carbon-carbon bonds. Such advancement consists of four late transition metal-catalyzed reactions based on the oxygenated chemical feedstock, which will be discussed on a chapter-by-chapter basis. Chapter 2 introduces our initial attempts to address a 40-year-old scientific challenge in the field of alcohol deoxygenation: how to selectively and efficiently remove hydroxyl groups in organic molecules without affecting other existing functional groups. We hypothesize a single-step, redox process to solve this problem, whereby the dehydrogenative oxidation of alcohols and the Wolff-Kishner reduction are combined. As a proof-of-concept discovery, the early development of this reaction is catalyzed by iridium complexes and mediated by hydrazine under forcing reaction conditions. This deoxygenation protocol proves effective for many simple activated substrates such as benzylic and allylic alcohols. The major limitation, however, is the poor reactivity and selectivity seen in aliphatic alcohol substrates. Chapter 3 describes the adaptation of ruthenium(II) catalysis for the direct deoxygenation of primary aliphatic alcohols in a completely chemo- and regio-selective manner. Such a robust catalytic system, comprising [Ru(p-cymene)Cl2]2 and 1,2-bis(dimethylphosphino)ethane, is vital to lower the activation energy barriers to the dehydrogenative oxidation of aliphatic alcohols, and makes this step more kinetically favorable. Equally important is the combination of KOt-Bu, DMSO and t-BuOH, which promotes the subsequent Wolff-Kishner reduction at low temperature. This method is thus more practical compared with the iridium-based protocol, proceeding under milder thermal conditions. Its synthetic utility is demonstrated by the selective cleavage of carbon-oxygen bonds in both simple and complex organic molecules such as steroids and alkaloids. Chapter 4 presents a synthetic approach to utilize naturally occurring carbonyl compounds (i.e. aldehydes and ketones) as more sustainable alkyl carbanion equivalents for formation of carbon-carbon bonds via carbonyl addition reactions. Traditionally, such transformations depend on organometallic reagents which are made from petroleum-derived chemical feedstocks and a stoichiometric quantity of metal. Accessing this new chemical reactivity of carbonyl compounds attributes to the ruthenium(II) catalytic system discovered in the early deoxygenation chemistry. By controlling the basicity, preformed carbonyl-derived hydrazones can intercept another carbonyl compounds to form new carbon-carbon bonds via a Zimmerman-Traxler chair-like transition state. This chemical transformation delivers a wide range of synthetically valuable secondary and tertiary alcohols. Additional highlights include excellent functional group compatibility and good stereochemical control governed by chiral amido and phosphine ligands. Chapter 5 focuses on the further exploration of such unique 'umpolung' reactivity for formation of carbon-carbon bonds via conjugate addition reactions. Inspired by the softness of ruthenium(II) pre-catalyst, which bears a resemblance to that of 'soft' transition metals in the classical 1,4-conjugate addition, we presume that this ruthenium(II)-based catalytic system may be more effective for conducting nucleophilic conjugate additions. Indeed, a variety of highly functionalized aromatic carbonyl compounds are used as latent benzyl carbanions, to couple with electron-deficient [alpha],[beta]-unsaturated compounds including esters, ketones, sulfones, phosphonates, and amides. Two bidentate phosphine ligands (dppp and dmpe) are found to facilitate this process in a complementary manner, largely depending on electronic profiles of the carbonyl compounds. Chapter 6 summarizes all research present in this thesis and contributions to knowledge advancement. " --
Book Synopsis Transition-metal-catalyzed Reactions by : Astrid Marisol Parsons
Download or read book Transition-metal-catalyzed Reactions written by Astrid Marisol Parsons and published by . This book was released on 2019 with total page 376 pages. Available in PDF, EPUB and Kindle. Book excerpt: "Transition-metal-catalyzed reactions have revolutionized the field of organic chemistry, enabling for the efficient synthesis of biologically and pharmaceutically relevant molecules. To this extent, this dissertation will focus on the development of new catalytic methods for the synthesis of organic molecules. Chapter 2 reports on the multimetallic Ni- and Pd- cross-electrophile coupling of vinyl bromides with vinyl triflates to form highly substituted 1,3-dienes. These dienes were subjected to Diels-Alder reactions and mechanistic experiments were performed to elucidate the reaction mechanism. Chapter 3 discusses the [Co(TPP)]-catalyzed (TPP = tetraphenylporphyrin) formation of substituted piperidines. Optimization studies, substrate screening, and mechanistic investigations will be discussed. Chapter 4 elaborates on how substitution on a variety of simple ketones and esters affects selectivity for C-H bond activation by tris-(3,5-dimethylpyrazolyl)borate rhodium complex. Lastly, Chapter 5 discusses the synthesis of novel bis((4,5-dihydrooxazol-2-yl)methyl)amine (ambox) ligated cobalt complexes. Importantly, this work provides the first insight into functionalization reactions of ambox-ligated cobalt complexes. Furthermore, these complexes are active towards hydrosilylation, hydroboration, C-C bond formation, and hydrogenation reactions alluding to the potential of this new class of cobalt-complexes for homogenous catalysis"--Page x.
Book Synopsis Addition Reactions with Unsaturated Hydrocarbons by : Ruimao Hua
Download or read book Addition Reactions with Unsaturated Hydrocarbons written by Ruimao Hua and published by John Wiley & Sons. This book was released on 2022-02-28 with total page 452 pages. Available in PDF, EPUB and Kindle. Book excerpt: Addition Reactions with Unsaturated Hydrocarbons Provides comprehensive coverage of the atom-economic approach to functionalized molecules using unsaturated hydrocarbons as starting materials Unsaturated hydrocarbons have emerged as an important class of fundamental starting materials in organic synthesis. Synthetic methodologies incorporating unsaturated hydrocarbons continue to expand due to their numerous applications in the synthesis of a vast array of chemicals. Addition Reactions with Unsaturated Hydrocarbons presents an up-to-date overview of modern methods that utilize reactions of unsaturated hydrocarbons as building blocks of organic synthesis, covering the conceptual and practical knowledge required for designing atom-efficient reactions to synthesize functionalized molecules. This authoritative volume discusses homo-dimerization and cross-dimerization of alkynes and/or alkenes, synthesis of carbonyl compounds from the hydration of alkynes, cycloadditions of alkynes and alkenes for the synthesis of carbocycles and heterocycles, double functionalization of alkynes and alkenes by addition reactions of element-element bonds, and more. Summarizes the most recent developments in the reactions of unsaturated hydrocarbons Features more than 600 schemes describing typical reactions starting from unsaturated hydrocarbons Covers topics such as alkynylated reactions, addition and cycloaddition reactions of alkynes and alkenes, and carbonylation of alkynes and alkenes with carbon monoxide Includes examples of synthesis procedures of natural products involving alkyne transformation With comprehensive coverage of important reactions of unsaturated hydrocarbons, Addition Reactions with Unsaturated Hydrocarbons is a valuable resource for organic chemists, pharmaceutical chemists, and biochemists in both academia and industry as well as an excellent reference text for graduate students in relevant areas of chemistry.
Book Synopsis Organic Reaction Mechanisms 2016 by : A. C. Knipe
Download or read book Organic Reaction Mechanisms 2016 written by A. C. Knipe and published by John Wiley & Sons. This book was released on 2019-12-30 with total page 872 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organic Reaction Mechanisms 2016, the 52nd annual volume in this highly successful and unique series, surveys research on organic reaction mechanisms described in the available literature dated 2016. The following classes of organic reaction mechanisms are comprehensively reviewed: • Reaction of Aldehydes and Ketones and their Derivatives • Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives • Oxidation and Reduction • Carbenes and Nitrenes • Nucleophilic Aromatic Substitution • Electrophilic Aromatic Substitution • Carbocations • Nucleophilic Aliphatic Substitution • Carbanions and Electrophilic Aliphatic Substitution • Elimination Reactions • Polar Addition Reactions • Cycloaddition Reactions • Molecular Rearrangements
