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Author: Rachel Motove Zeldin
Publisher:
ISBN:
Category :
Languages : en
Pages : 532
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Book Description
The modern era of synthetic chemistry can be characterized by increased understanding, development and application of transition metal complexes to traditionally organic transformations. While the field has focused largely on the chemistry of group 4-8 metals (and in particular, rhodium and palladium), there has been growing interest in the past decade in using so-called "coinage metals"--Gold, silver and copper--as catalysts for organic reactions. Gold(I) metal complexes have been shown to effect a range of organic transformations that proceed through [pi]-activation mechanisms, often with greater selectivity than other transition metal complexes. Additionally, in contrast to more established transition metal reactions, gold(I) processes can be conducted at low temperature and in the presence of water and air. Because of their mild conditions and high degree of control, gold(I) reactions are ideal for application to total synthesis. In the first chapter of this text, we discuss the current state of the art of gold(I)-catalysis in the context of complex molecule synthesis. The reactivity exhibited by gold(I) complexes is highly controlled by choice of catalyst ligand. In the second chapter, we discuss the development of ligand-controlled intramolecular reaction of dienes and allenes to afford selectively either [4+2]- or [4+3] cycloadducts. The purpose of this discussion is two-fold: first, to demonstrate the effect that stabilization of reactive intermediates has on the course of gold(I) reactions, and second, to develop methodologies aimed at constructing novel, complex ring structures. In the third chapter of this text, we take one of the reactions discovered in the course of our work in diene-allene cycloadditions and apply it to the total synthesis of antimalarial bisindole alkaloids flinderoles B and C. The key step, a gold(I)-catalyzed hydroarylation of an allene using a C2-indole nucleophile, simulatenously installs three of four unique structural motifs of this natural product.
Author: Rachel Motove Zeldin
Publisher:
ISBN:
Category :
Languages : en
Pages : 532
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Book Description
The modern era of synthetic chemistry can be characterized by increased understanding, development and application of transition metal complexes to traditionally organic transformations. While the field has focused largely on the chemistry of group 4-8 metals (and in particular, rhodium and palladium), there has been growing interest in the past decade in using so-called "coinage metals"--Gold, silver and copper--as catalysts for organic reactions. Gold(I) metal complexes have been shown to effect a range of organic transformations that proceed through [pi]-activation mechanisms, often with greater selectivity than other transition metal complexes. Additionally, in contrast to more established transition metal reactions, gold(I) processes can be conducted at low temperature and in the presence of water and air. Because of their mild conditions and high degree of control, gold(I) reactions are ideal for application to total synthesis. In the first chapter of this text, we discuss the current state of the art of gold(I)-catalysis in the context of complex molecule synthesis. The reactivity exhibited by gold(I) complexes is highly controlled by choice of catalyst ligand. In the second chapter, we discuss the development of ligand-controlled intramolecular reaction of dienes and allenes to afford selectively either [4+2]- or [4+3] cycloadducts. The purpose of this discussion is two-fold: first, to demonstrate the effect that stabilization of reactive intermediates has on the course of gold(I) reactions, and second, to develop methodologies aimed at constructing novel, complex ring structures. In the third chapter of this text, we take one of the reactions discovered in the course of our work in diene-allene cycloadditions and apply it to the total synthesis of antimalarial bisindole alkaloids flinderoles B and C. The key step, a gold(I)-catalyzed hydroarylation of an allene using a C2-indole nucleophile, simulatenously installs three of four unique structural motifs of this natural product.
Author: Antoine Simonneau
Publisher: Springer
ISBN: 3319067079
Category : Science
Languages : en
Pages : 261
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Book Description
Antoine Simonneau's thesis highlights the development of new cycloisomerization reactions through the activation of alkynes with gold complexes. First Simonneau describes 1,6-enynes and their direct conversion into allenes through 1,5-hydride or ester migration processes. The author and his team used appropriate propargylic functional groups to achieve this conversion. This study shows that O-tethered 1,6-enynes carrying a strained cycloalkane at the propargylic position could undergo a cyclopropanation/ring expansion cascade reaction. The author employed this rearrangement as the starting point in the design of a new macro cycle synthesis. The next part of the thesis focuses on the cycloisomerization of diynes involving as the first step of the process the rearrangement of one alkyne partner into an allene thanks to a gold-catalyzed 1,3-shift of a propargylic ester. The thesis discloses a new cycloisomerization pattern featuring a 1,5-carbonyl transfer, giving rise to unprecedented cross-conjugated diketones. In the final part of the research, Simmoneau investigates the gold-catalyzed cycloisomerization mechanism of 1,6-enynes and questions the intermediacy of gold acetylides. By the means of NMR and mass spectrometry analysis, theoretical treatment and solution experiments, it was possible to rule out the involvement of these species in the catalytic cycle. This thesis has led to a number of publications in high-impact journals.
Author: A. Stephen K. Hashmi
Publisher: John Wiley & Sons
ISBN: 3527319522
Category : Science
Languages : en
Pages : 419
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Book Description
With its impressive features, gold has led to completely new reaction types in recent years, which in turn have strongly influenced both organic catalysis and material science. Other fields where a significant amount of new results has been obtained include nanotechnology, self assembly/supramolecular systems and biochemical/medicinal chemistry. As a result, gold is one of the hottest topics in catalysis at the moment, with an increasing amount of research being carried out in this field. While focusing on homogeneous catalysis, this monograph also covers the main applications in heterogeneous catalysis. Following a look at the gold-catalyzed addition of heteroatom nucleophiles to alkynes, it goes on to discuss gold-catalyzed additions to allenes and alkenes, gold-catalyzed benzannulations, cycloisomerization and rearrangement reactions, as well as oxidation and reduction reactions. The whole is finished off with a section on gold-catalyzed aldol and related reactions and the application of gold-catalyzed reactions to natural product synthesis. Of interest to synthetic chemists and inorganic chemists, as well as organic chemists working in homogeneous catalysis, physical and technical chemists.
Author: LeGrande M. Slaughter
Publisher: Springer
ISBN: 3319137220
Category : Science
Languages : en
Pages : 292
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Book Description
The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience. Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field. Review articles for the individual volumes are invited by the volume editors. Readership: research chemists at universities or in industry, graduate students.
Author: Veronique Michelet
Publisher: World Scientific
ISBN: 1783265558
Category : Science
Languages : en
Pages : 564
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Book Description
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.
Author: Chao-Jun Li
Publisher: John Wiley & Sons
ISBN: 3527807691
Category : Science
Languages : en
Pages : 400
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Book Description
Covers all the aspects of the recent achievements in silver catalyzed reactions Silver catalysis has emerged as a powerful tool in the field of organic synthesis. This comprehensive book systematically explores the unique performance of silver catalysis, introducing all the recent progress of silver catalysis in organic synthesis. It clearly emphasizes the unique features of silver catalysis and provides the reaction mechanism involved. This two-volume book also provides vivid schematics and tables throughout to enhance the accessibility to the relevant theory and mechanisms. Silver Catalysis in Organic Synthesis begins with an introduction to Silver Chemistry before moving on to chapters covering: Silver-Catalyzed Cycloaddition Reactions; Silver-Catalyzed Cyclizations; Silver-Mediated Radical Reactions; Silver-Mediated Fluorination, Perfluoroalkylation and Trifluoromethylthiolation Reactions; Coupling Reactions and C-H Functionalization; Silver-Catalyzed CO2 Incorporation; Silver-Catalyzed Carbene, Nitrene, and Silylene Transfer Reactions; Asymmetric Silver-Catalyzed Reactions; Silver-Catalyzed Reduction and Oxidation of Aldehydes and Their Derivatives; Silver Complexes in Organic Transformations; and Silver Nanoparticles in Organic Transformations. -Covers recently developed organic reactions catalyzed by silver, along with their reaction mechanism -Introduces many new reactions and mechanisms related to silver catalysis -Offers professionals and newcomers in the related fields a survey of new advances in silver catalysis in organic synthesis Silver Catalysis in Organic Synthesis will appeal to a wide readership including chemists, biochemists, pharmaceutical scientists, biomedical researchers, agriculture scientists, and graduate students in the related fields.
Author: Takahiko Akiyama
Publisher: John Wiley & Sons
ISBN: 1119736412
Category : Science
Languages : en
Pages : 798
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Book Description
Catalytic Asymmetric Synthesis Seminal text presenting detailed accounts of the most important catalytic asymmetric reactions known today This book covers the preparation of enantiomerically pure or enriched chemical compounds by use of chiral catalyst molecules. While reviewing the most important catalytic methods for asymmetric organic synthesis, this book highlights the most important and recent developments in catalytic asymmetric synthesis. Edited by two well-qualified experts, sample topics covered in the work include: Metal catalysis, organocatalysis, photoredox catalysis, enzyme catalysis C–H bond functionalization reactions Carbon–carbon bond formation reactions, carbon–halogen bond formation reactions, hydrogenations, polymerizations, flow reactions Axially chiral compounds Retaining the best of its predecessors but now thoroughly up to date with the important and recent developments in catalytic asymmetric synthesis, the 4th edition of Catalytic Asymmetric Synthesis serves as an excellent desktop reference and text for researchers and students, from upper-level undergraduates all the way to experienced professionals in industry or academia.
Author: Jianbo Wang
Publisher: John Wiley & Sons
ISBN: 3527829156
Category : Science
Languages : en
Pages : 450
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Book Description
Presents an up-to-date overview of the rapidly growing field of carbene transformations Carbene transformations have had an enormous impact on catalysis and organometallic chemistry. With the growth of transition metal-catalyzed carbene transformations in recent decades, carbene transformations are today an important compound class in organic synthesis as well as in the pharmaceutical and agrochemical industries. Edited by leading experts in the field, Transition Metal-Catalyzed Carbene Transformations is a thorough summary of the most recent advances in the rapidly expanding research area. This authoritative volume covers different reaction types such as ring forming reactions and rearrangement reactions, details their conditions and properties, and provides readers with accurate information on a wide range of carbene reactions. Twelve in-depth chapters address topics including carbene C-H bond insertion in alkane functionalization, the application of engineered enzymes in asymmetric carbene transfer, progress in transition-metal-catalyzed cross-coupling using carbene precursors, and more. Throughout the text, the authors highlight novel catalytic systems, transformations, and applications of transition-metal-catalyzed carbene transfer. Highlights the dynamic nature of the field of transition-metal-catalyzed carbene transformations Summarizes the catalytic radical approach for selective carbene cyclopropanation, high enantioselectivity in X-H insertions, and bio-inspired carbene transformations Introduces chiral N,N'-dioxide and chiral guanidine-based catalysts and different transformations with gold catalysis Discusses approaches in cycloaddition reactions with metal carbenes and polymerization with carbene transformations Outlines multicomponent reactions through gem-difunctionalization and transition-metal-catalyzed cross-coupling using carbene precursors Transition Metal-Catalyzed Carbene Transformations is essential reading for all chemists involved in organometallics, including organic and inorganic chemists, catalytic chemists, and chemists working in industry.
Author: Ramon Rios Torres
Publisher: John Wiley & Sons
ISBN: 1118308638
Category : Science
Languages : en
Pages : 422
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Book Description
The Pauson-Khand reaction is an important reaction in the field of organic chemistry. It involves the transition-metal catalysed cycloaddition of an alkyne, an alkene and carbon monoxide, to produce cyclopentenones. The importance of this reaction originates from its high value in transforming simple components into the synthetically useful cyclopentenone unit, in which a high degree of molecular complexity can be achieved in a single step, with impressive stereochemical and regiochemical control. The Pauson-Khand Reaction investigates the nature and many variations of this reaction. Topics covered include: the mechanisms of Pauson‐Khand-type reactions non chiral intramolecular and intermolecular versions of Pauson‐Khand reactions asymmetric Pauson‐Khand reaction using chiral auxiliaries the enantioselective Pauson‐Khand reaction Pauson‐Khand reactions catalysed by metals other than cobalt unconventional Pauson‐Khand reactions the Pauson‐Khand reaction in total synthesis Presenting a comprehensive overview of this fundamental reaction, The Pauson-Khand Reaction will find a place on the bookshelves of any organic or organometallic chemist.
Author: Bunsho Ohtani
Publisher: Frontiers Media SA
ISBN: 2889667863
Category : Science
Languages : en
Pages : 163
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Book Description
