[PDF] Palladium And Nickel Catalyzed Transformations Forming Functionalized Dihydroisoquinolinones Chromans Dihydrobenzofurans And Oxindoles eBook

Author : Hyung Yoon
Publisher : Springer Nature
Page : 236 pages
File Size : 46,82 MB
Release : 2020-09-02
Category : Science
ISBN : 3030540774

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This book presents Pd- and Ni-catalyzed transformations generating functionalized heterocycles. Transition metal catalysis is at the forefront of synthetic organic chemistry since it offers new and powerful methods to forge carbon–carbon bonds in high atom- and step-economy. In Chapter 1, the author describes a Pd- and Ni-catalyzed cycloisomerization of aryl iodides to alkyl iodides, known as carboiodination. In the context of the Pd-catalyzed variant, the chapter explores the production of enantioenriched carboxamides through diastereoselective Pd-catalyzed carboiodination. It then discusses Ni-catalyzed reactions to generate oxindoles and an enantioselective variant employing a dual ligand system. Chapter 2 introduces readers to a Pd-catalyzed diastereoselective anion-capture cascade. It also examines diastereoselective Pd-catalyzed aryl cyanation to synthesize alkyl nitriles, a method that generates high yields of borylated chromans as a single diastereomer, and highlights its synthetic utility. Lastly, Chapter 3 presents a Pd-catalyzed domino process harnessing carbopalladation, C–H activation and π-system insertion (benzynes and alkynes) to generate spirocycles. It also describes the mechanistic studies performed on these reactions.

Author : James Thomas Masters
Publisher :
Page : pages
File Size : 18,47 MB
Release : 2016
Category :
ISBN :

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The continued demand for efficient chemo-, regio-, and stereoselective organic transformations motivates the development of new chemical reactions. Transition metal catalysis represents a powerful method for the construction of carbon-carbon, carbon-hydrogen, and carbon-heteroatom bonds in a highly selective fashion. This dissertation describes the development of several new transition metal-catalyzed organic reactions useful in the preparation of various chiral small molecules, including both fundamental organic "building block" compounds and structurally complex natural products and pharmaceutical agents. We report a new strategy for the synthesis of chiral beta-alkynyl esters, ketones, and sulfones via sequential palladium-catalyzed carbon-carbon bond formation and copper-catalyzed carbon-hydrogen bond formation. The process is operationally straightforward, compatible with a broad range of substrates, and delivers the targets in high yields with excellent levels of enantioselectivity. It is compatible with both oxygen and nitrogen functionality, and this enabled the rapid elaboration of the products into a diverse set of chiral heterocycles. The sequential catalysis protocol was employed in a concise, enantioselective synthesis of AMG 837, a potent agonist of G-protein coupled receptor 40. Recognizing both the biological relevance of chiral alkaloids and the synthetic challenges associated with the construction of quaternary, all-carbon stereocenters, we pursued a palladium-catalyzed asymmetric allylic alkylation that effected carbon-carbon bond formation on prochiral oxindole nucleophiles. Although prior research has demonstrated that allylic alkylation reactions of geminal dicarboxylate electrophiles typically yield branched products as the result of ipso-addition, we identify conditions wherein oxindoles react with a dipivaloyl electrophile to afford linear enol pivalate compounds. A mild hydrolysis reaction converts these products into the aldehyde that formally results from asymmetric conjugate addition to acrolein, a challenging transformation with limited literature precedent. These adducts are established precursors to tricyclic alkaloid scaffolds of pharmaceutical interest. Chiral gamma-heteroatom-substituted cycloalkenones are well-established organic "building blocks" that are widely used in the synthesis of complex molecules. The exposure of meso-1,4-allylic dibenzoates to chiral phosphine-ligated palladium salts in the presence of a potassium nitronate nucleophile promotes a unique oxidative desymmetrization reaction. This process yields enantiopure gamma-benzoyloxy cyclopentenones, cyclohexenones, and cycloheptenones. We describe the elaboration of these products into diverse, enantioenriched oxygen- and nitrogen-substituted cycloalkenones via subsequent palladium-catalyzed allylic alkylation reactions involving heteroatom nucleophiles. Separately, we employ enantiopure gamma-benzoyloxy cyclohexenones in short, asymmetric syntheses of enantio- and diastereomerically diverse epoxyquinoid natural products. We further highlight the utility of palladium catalysis in complex molecule synthesis through the development of a unique, intramolecular carbon-carbon bond-forming reaction that generates a strained enyne and through an asymmetric formal synthesis of aliskiren, a renin inhibitor used in the treatment of hypertension.

Author : Aiwen Lei
Publisher : John Wiley & Sons
Page : 240 pages
File Size : 24,43 MB
Release : 2016-08-12
Category : Technology & Engineering
ISBN : 3527681019

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The first handbook on this emerging field provides a comprehensive overview of transition metal-catalyzed coupling reactions in the presence of an oxidant. Following an introduction to the general concept and mechanism of this reaction class, the team of authors presents chapters on C-C cross-coupling reactions using organometallic partners, C-Heteroatom bond forming reactions via oxidative couplings, and C-H couplings via C-H activation. The text also covers such groundbreaking topics as recent achievements in the fields of C-C and C-X bond formation reactions as well as C-H activation involving oxidative couplings. With its novel and concise approach towards important building blocks in organic chemistry and its focus on synthetic applications, this handbook is of great interest to all synthetic chemists in academia and industry alike.

Author : Tamejiro Hiyama
Publisher : John Wiley & Sons
Page : 566 pages
File Size : 30,98 MB
Release : 2020-02-18
Category : Science
ISBN : 3527344535

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Provides a unique summary of important catalytic reactions in the presence of silicon A must-have for all synthetic chemists, this book summarizes all of the important developments in the application of organosilicon compounds in organic synthesis and catalysis. Edited by two world leaders in the field, it describes different approaches and covers a broad range of reactions, e.g. catalytic generation of silicon nucleophiles, Si-H Bond activation, C-H bond silylation, silicon-based cross-coupling reactions, and hydrosilylation in the presence of earth-abundant metals. In addition to the topics covered above, Organosilicon Chemistry: Novel Approaches and Reactions features chapters that look at Lewis base activation of silicon Lewis acids, silylenes as ligands in catalysis, and chiral silicon molecules. -The first book about this topic in decades, covering a broad range of reactions -Covers new approaches and novel catalyst systems that have been developed in recent years -Written by well-known, international experts in the areas of organometallic silicon chemistry and organosilicon cross-coupling reactions Organosilicon Chemistry: Novel Approaches and Reactions is an indispensable source of information for synthetic chemists in academia and industry, working in the field of organic synthesis, catalysis, and main-group chemistry.

Author : Aziz M. Muzafarov
Publisher : Springer Science & Business Media
Page : 242 pages
File Size : 25,84 MB
Release : 2010-09-22
Category : Technology & Engineering
ISBN : 3642160476

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Modern Synthetic and Application Aspects of Polysilanes: An Underestimated Class of Materials?, by A. Feigl, A. Bockholt, J. Weis, and B. Rieger; * Conjugated Organosilicon Materials for Organic Electronics and Photonics, by Sergei A. Ponomarenko and Stephan Kirchmeyer; * Polycarbosilanes Based on Silicon-Carbon Cyclic Monomers, by E.Sh. Finkelshtein, N.V. Ushakov, and M.L. Gringolts; * New Synthetic Strategies for Structured Silicones Using B(C6F5)3, by Michael A. Brook, John B. Grande, and François Ganachaud; * Polyhedral Oligomeric Silsesquioxanes with Controlled Structure: Formation and Application in New Si-Based Polymer Systems, by Yusuke Kawakami, Yuriko Kakihana, Akio Miyazato, Seiji Tateyama, and Md. Asadul Hoque;

Author : Richard G Jones
Publisher : Royal Society of Chemistry
Page : 214 pages
File Size : 25,47 MB
Release : 2023-09-08
Category : Technology & Engineering
ISBN : 183767244X

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Silicon-containing Polymers reflects the growing interest worldwide in this developing field. Silicon polymers are now finding use as moulding materials, rubbers, ceramic precursors, in lithography and reprography as photosensitive materials, as conducting polymers, and in a host of other applications. This book presents up-to-date research from all over the world. It brings together research from the forefront of a multidisciplinary subject, covering the synthesis, modification, characterization, properties and applications of polysiloxanes, polysilylenes, polysilazanes and organosilicate derivatives. Silicon-containing Polymers will be of interest to researchers and postgraduates in any area of materials science, as well as some areas of inorganic chemistry.

Author : D.M. Roundhill
Publisher : Springer Science & Business Media
Page : 364 pages
File Size : 32,10 MB
Release : 2013-06-29
Category : Science
ISBN : 1489914951

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Focusing on practical applications, the author provides a balanced introduction to the many possible technological uses of metal complexes. Coverage includes the transition metals, lanthanide and actinide complexes, metal porphyrins, and many other complexes. This volume meets the needs of students and scientists in inorganic chemistry, chemical physics, and solid-state physics.

Author : John Connolly
Publisher : Elsevier
Page : 457 pages
File Size : 13,19 MB
Release : 2012-12-02
Category : Technology & Engineering
ISBN : 0323149707

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Photochemical Conversion and Storage of Solar Energy contains the proceedings of the Third International Conference on Photochemical Conversion and Storage of Solar Energy held in Boulder, Colorado, on August 3-8, 1980. The papers review the state of the art in the areas of photochemistry and photoelectrochemistry in the context of solar energy conversion and storage. Topics covered include photosynthetic quantum conversion; biomimetic systems for solar energy conversion; and photochemical electron transfer reactions in homogeneous solutions. This volume is comprised of 11 chapters and begins by describing an artificial photosynthetic system that can capture solar quanta and convert them into a stable chemical form. The discussion then turns to biomimetic approaches to solar energy conversion; fluorescent concentrators for photovoltaic cells; requirements for homogeneous photoredox chemistry in inorganic systems; and the use of inorganic components coupled with catalysts in heterogeneous assemblies for photochemical water splitting. The following chapters focus on photogalvanic cells, electrochemical photovoltaic cells, and photoelectrosynthetic reactions at the semiconductor-electrolyte interface. The final chapter examines the thermodynamic limits on photoconversion and storage of solar energy. This monograph will be of interest to chemists and other scientists concerned with the photochemical aspects of solar energy conversion and storage.