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This book is a comprehensive text covering the research and development trends in the booming field of transition metal catalyzed oxidative cross-coupling reactions. Oxidative cross-coupling reaction is a new method to forming chemical bonds besides the traditional cross-coupling reactions. This book provides the answers to how this coupling reaction occurs and what its advantages are. The palladium, copper and iron catalyzed oxidative cross-coupling reactions as the main focuses of interest are described in detail. The oxidative cross-coupling reactions catalyzed by other metals and transition-metal-free oxidative coupling reactions are also introduced.This book provides a useful reference source for researchers and graduates in the field of transition metal catalyzed coupling reactions. It is also valuable to researchers working in pharmaceutical companies, fine organic chemical companies, and etc.
In the second half of dissertation, two studies with regard to traditional cross-coupling reactions of aryl chlorides with organometallic reagents are carried out. Firstly, palladium-catalyzed Hiyama cross-coupling reaction of aryl and heteroaryl chlorides with aryl and heteroaryltrialkoxysilanes under solvent-free reaction condition is presented. The catalyst system comprising of Pd(OAc)2́2 and PCy2́2-Andolephos (Chapter 6, L2) is a highly effective for this coupling reaction with low catalyst loading (down to 0.05 mol% Pd) and short reaction time (3 h). A broad substrate scope containing electron-rich, -neutral, and -deficient and sterically hindered aryl chlorides is achieved. Notably, the first general examples of Hiyama cross-coupling reaction using heteroaryltrialkoxysilanes are demonstrated. The presence of acetic acid or water suppresses the decomposition of aryl chlorides and promotes the product yields. A large scale experiment without degasification and purification of reactants is also conducted smoothly. Last but not least, a general palladium-catalyzed borylation of aryl chlorides with pinacol borane is reported. A newly modified indolylphosphine ligand (Chapter 7, L18) is prepared via an efficient protocol involving Fischer indolization from readily available phenylhydrazine and 2'-hydroxyacetophenone. The combination of Pd(dba)2́2 and newly modified indolylphosphine ligand (Chapter 7, L18) are shown to be an effective catalyst for the borylation of non-activated and activated aryl chlorides with pinacol borane. Addition of tetra-n-butylammoniumiodide (TBAI) is highly effective for coupling of aryl chlorides bearing function groups such as keto, nitile and ester. 1 mol% Pd catalyst loading can be achieved using this catalytic system.
Cross-coupling reactions involving C-H and C-X bond functionalisation are commonplace in natural product synthesis and natural products, therapeutic agents, biological probes, and advanced materials. Much attention has been given to understanding the mechanistic strategies used to achieve this, making this a hot topic in recent years. In this edited book, contributions from across the globe examine these strategies, with a particular focus on palladium and copper, as well as iron – an emerging element in this field. Reviewing the recent literature, the book presents an in-depth understanding of the field, guiding the reader to achieving the best synthetic strategies for aromatic functionalisation. Organic and Organometallic chemists, as well as natural product and pharmaceutical scientists, will find this an essential guide to a major transformation currently underway in synthetic chemistry.
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.
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.
Transition-Metal-Catalyzed C-H Functionalization of Heterocycles A comprehensive guide to recent advances in this field Constituting the majority of all known compounds, heterocycles are structures that incorporate one or more heteroatoms within their core, thus exhibiting properties that are quite different from their all-carbon analogs. They are fundamental to all fields of chemistry and, therefore, their synthesis and modification has attracted a great deal of attention in the recent years. In this vein, transition-metal-catalyzed C-H bond functionalization forms a crucial tool for generating and analyzing heterocyclic compounds. Transition-Metal-Catalyzed C-H Functionalization of Heterocycles, Two-Volume Set, showcases diverse C-H functionalization methodologies and their incorporation into the latest research. The chapters serve as an essential tool depicting detailed site-selective functionalization of heterocyclic cores, along with a comprehensive discussion on their mechanistic approaches. Readers of Transition-Metal-Catalyzed C-H Functionalization of Heterocycles, Two-Volume-Set will also find: A detailed introduction to C-H activation along with the mechanistic aspects of transition-metal-catalyzed C-H bond activation reactions Easy-to-use structures with each chapter dedicated to a type of heterocycle and its specific functionalization methodologies A leading team of international authors in C-H bond functionalization Transition-Metal-Catalyzed C-H Functionalization of Heterocycles, Two-Volume-Set is a valuable guide for students and researchers in organic synthesis and process development, in both academic and industrial contexts.
This book highlights major achievements made in the last five years concerning sustainable C(sp3)-H bond functionalization and offers a promising and emerging tool-kit for organic synthesis. The book is divided into three chapters demonstrating key advances in C(sp3)-H bond functionalization. Chapter 1 reviews transition-metal-catalyzed C(sp3)-H bond functionalization using different directing groups, while Chapter 2 addresses the new methods of transition-metal-catalyzed and metal-free C(sp3)-H bond functionalization without directing groups, in addition to briefly highlighting redox-neutral C(sp3)-H bond functionalization. In closing, Chapter 3 examines visible-light photoredox catalysis, an emerging and highly sustainable C(sp3)-H bond functionalization strategy. The book offers an intriguing and useful reference guide for a broad readership working and/or interested in the fields of organic, organometallic, and green chemistry.
Modular C-H functionalization methods offer a direct approach to molecular derivatization. In "radical relay" C-H functionalization reactions, a C(sp3)-H bond can be abstracted by an H atom transfer (HAT) reagent to form an alkyl radical. It has been demonstrated that alkyl radicals can be cross coupled with nucleophilic coupling partners in the presence of transition metal catalysts or reacted directly with compatible radical traps to form new bonds. Such oxidative coupling reactions allow bond construction from otherwise unreactive C-H sites enabling conversion of simple molecular building blocks into value added product libraries and generation of structural analogues of important molecules that can be tested for improved properties. This thesis discloses the development, mechanistic understanding, and application of several oxidative cross coupling methods including C(sp3)-H arylation, fluorination, and methylation reactions as well as an aerobic oxidative amidation reaction between alcohols and amines. Collectively, these methods contribute to the breadth of oxidation reactions available for the synthesis and functionalization of diverse molecules. The C-H arylation, fluorination/fluoride displacement, and amide coupling all are opportunities to apply oxidative coupling directly to the synthesis of important molecules. Complementarily, the fluorination and methylation reactions present opportunities to functionalize existing molecules to allow derivatized compositions of matter to be accessed for testing. Both forms of methodology are appealing for application in synthesis-driven specialties, where rapid and direct access to new structures is essential to solving complex challenges
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.
The series Topics in Organometallic Chemistry presents critical overviews of research results in organometallic chemistry. As our understanding of organometallic structure, properties and mechanisms increases, new ways are opened for the design of organometallic compounds and reactions tailored to the needs of such diverse areas as organic synthesis, medical research, biology and materials science. Thus the scope of coverage includes a broad range of topics of pure and applied organometallic chemistry, where new breakthroughs are being achieved that are of significance to a larger scientific audience. The individual volumes of Topics in Organometallic Chemistry are thematic. Review articles are generally invited by the volume editors. All chapters from Topics in Organometallic Chemistry are published OnlineFirst with an individual DOI. In references, Topics in Organometallic Chemistry is abbreviated as Top Organomet Chem and cited as a journal.