New Transformations In The Transition Metal Catalyzed Hydrofunctionalization Of Alkynes
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New Transformations In The Transition Metal Catalyzed Hydrofunctionalization Of Alkynes
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Author : Megan Armstrong
language : en
Publisher:
Release Date : 2021
New Transformations In The Transition Metal Catalyzed Hydrofunctionalization Of Alkynes written by Megan Armstrong and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 2021 with categories.
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.
Hydrofunctionalization
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Author : Valentine P. Ananikov
language : en
Publisher: Springer
Release Date : 2012-09-29
Hydrofunctionalization written by Valentine P. Ananikov and has been published by Springer this book supported file pdf, txt, epub, kindle and other format this book has been release on 2012-09-29 with Science categories.
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.
Part 1
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Author : Derek Schipper
language : en
Publisher:
Release Date : 2011
Part 1 written by Derek Schipper and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 2011 with Aromatic compounds categories.
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.
Electrochemical Induced Hydrofunctionalizations Of Alkenes And Alkynes
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Author : Yahui Zhang
language : en
Publisher: OAE Publishing Inc.
Release Date : 2024-03-01
Electrochemical Induced Hydrofunctionalizations Of Alkenes And Alkynes written by Yahui Zhang and has been published by OAE Publishing Inc. this book supported file pdf, txt, epub, kindle and other format this book has been release on 2024-03-01 with Science categories.
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.
Addition Reactions With Unsaturated Hydrocarbons
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Author : Ruimao Hua
language : en
Publisher: John Wiley & Sons
Release Date : 2022-02-28
Addition Reactions With Unsaturated Hydrocarbons written by Ruimao Hua and has been published by John Wiley & Sons this book supported file pdf, txt, epub, kindle and other format this book has been release on 2022-02-28 with Science categories.
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.
Transition Metal Catalyzed Functionalization Of Alkynes
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Author : Avijit Hazra
language : en
Publisher:
Release Date : 2021
Transition Metal Catalyzed Functionalization Of Alkynes written by Avijit Hazra and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 2021 with categories.
Organic Reaction Mechanisms 2016
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Author : A. C. Knipe
language : en
Publisher: John Wiley & Sons
Release Date : 2019-12-30
Organic Reaction Mechanisms 2016 written by A. C. Knipe and has been published by John Wiley & Sons this book supported file pdf, txt, epub, kindle and other format this book has been release on 2019-12-30 with Science categories.
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
Advances In Organometallic Chemistry
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Author : Pedro J. Perez
language : en
Publisher: Academic Press
Release Date : 2020-06-06
Advances In Organometallic Chemistry written by Pedro J. Perez and has been published by Academic Press this book supported file pdf, txt, epub, kindle and other format this book has been release on 2020-06-06 with Science categories.
Advances in Organometallic Chemistry, Volume 74, the latest release in this longstanding serial, is known for its comprehensive coverage of topics in organometallic synthesis, reactions, mechanisms, homogeneous catalysis, and more. It is ideal for a wide range of researchers involved in organometallic chemistry, with this updated release including chapters on Metal dendrimers used in biomedical applications, Sigma-bond activation reactions induced by unsaturated osmium (IV) complexes with bulky phosphines, Base metal pincer complexes, and more. Contains contributions from leading authorities in the field of organometallic chemistry Covers topics in organometallic synthesis, reactions, mechanisms, homogeneous catalysis, and more Informs and updates readers on the latest developments in the field Carefully edited to provide easy-to-read material
Gold Catalysis An Homogeneous Approach
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Author : Veronique Michelet
language : en
Publisher: World Scientific
Release Date : 2014-06-20
Gold Catalysis An Homogeneous Approach written by Veronique Michelet and has been published by World Scientific this book supported file pdf, txt, epub, kindle and other format this book has been release on 2014-06-20 with Science categories.
Research on designing new catalytic systems has been one of the most important fields in modern organic chemistry. One reason for this is the predominant contribution of catalysis to the concepts of atom economy and green chemistry in the 21st century. Gold, considered catalytically inactive for a long time, is now a fascinating partner of modern chemistry, as scientists such as Bond, Teles, Haruta, Hutchings, Ito and Hayashi opened new perspectives for the whole synthetic chemist community. This book presents the major advances in homogeneous catalysis, emphasizing the methodologies that create carbon-carbon and carbon-heteroatom bonds, the applications that create diversity and synthesize natural products, and the recent advances and challenges in asymmetric catalysis and computational research.It provides readers with in-depth information about homogeneous gold-catalyzed reactions and presents several explanations for the scientific design of a catalyst. Readers will be able to understand the entire gold area and find solutions to problems in catalysis.Gold Catalysis — An Homogeneous Approach is part of the Catalytic Science Series and features prominent authors who are experts in their respective fields.
Ammonia And Hydrazine Transition Metal Catalyzed Hydroamination And Metal Free Catalyzed Functionalization
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Author :
language : en
Publisher:
Release Date : 2012
Ammonia And Hydrazine Transition Metal Catalyzed Hydroamination And Metal Free Catalyzed Functionalization written by and has been published by this book supported file pdf, txt, epub, kindle and other format this book has been release on 2012 with categories.
The efficient and selective preparation of organic molecules is critical for mankind. For the future, it is of paramount importance to find catalysts able to transform abundant and cheap feedstocks into useful compounds. Acyclic and heterocyclic nitrogen-containing derivatives are common components of naturally occurring compounds, agrochemicals, cosmetics, and pharmaceuticals; they are also useful intermediates in a number of industrial processes. One of the most widely used synthetic strategies, allowing the formation of an N-C bond, is the addition of an N-H bond across a carbon-carbon multiple bond, the so-called hydroamination reaction. This chemical transformation fulfills the principle of "green chemistry" since it ideally occurs with 100% atom economy. Various catalysts have been found to promote this reaction, although many limitations remain; one of the most prominent is the lack of methods that permit the use of NH3 and NH2NH2 as the amine partners. In fact, ammonia and hydrazine have rarely succumbed to homogeneous catalytic transformations. Considering the low cost and abundance of ammonia (136 million metric tons produced in 2011) and hydrazine, catalysts able to improve the reactivity and selectivity of the NH3- and NH2NH2-hydroamination reaction, and more broadly speaking the functionalization of these chemicals, are highly desirable. In the last funded period, we discovered the first homogeneous catalysts able to promote the hydroamination of alkynes and allenes with ammonia and the parent hydrazine. The key feature of our catalytic systems is that the formation of catalytically inactive Werner complexes is reversible, in marked contrast to most of the known ammonia and hydrazine transition metal complexes. This is due to the peculiar electronic properties of our neutral ancillary ligands, especially their strong donating capabilities. However, our catalysts currently require high temperatures and long reaction times. To address this issue, we have developed several new families of carbon- and boron-based ligands, which are even better donors. The corresponding metal complexes (particularly gold, rhodium, iridium, and ruthenium) of all these species will be tested in the Markovnikov and anti-Markovnikov hydroamination of alkynes, allenes, and also alkenes with ammonia and hydrazine. We will also develop metal-free catalytic processes for the functionalization of ammonia and hydrazine. By possessing both a lone pair of electrons and an accessible vacant orbital, singlet carbenes resemble and can mimic the chemical behavior of transition metals. Our preliminary results demonstrate that specially designed carbenes can split the N-H bond of ammonia by an initial nucleophilic activation that prevents the formation of Lewis acid-base adducts, which is the major hurdle for the transition metal catalyzed functionalization of NH3. The use of purely organic compounds as catalysts will eliminate the major drawbacks of transition-metal-catalysis technology, which are the excessive cost of metal complexes (metal + ligands) and in many cases the toxicity of the metal.