Download or read book Palladium catalyzed Heck Reaction and Tandem Cross Coupling Reactions for Heterocycle Synthesis written by Yuanqing Fang and published by . This book was released on 2007 with total page 1130 pages. Available in PDF, EPUB and Kindle. Book excerpt: We have obtained a tetracyclic Heck product with a formal anti-beta -hydride elimination during our post-ARO Pd-catalyzed derivatization studies of dihydronaphthalenes. We found that the yield for this Heck reaction was highly base-dependent, with DABCO being optimal. The catalyst combination of Pd2(dba)3/HP(tBu)3·BF 4 and DABCO was highly efficient for this intramolecular Heck reaction under very mild conditions. Additionally, we observed tandem double Heck reactions, which selectively functionalize two C-Br bonds intra- and intermolecularly. We further developed the concept of selective intramolecular and intermolecular cross-couplings using more general gemdihaloolefin systems, which subsequently led to the development of a variety of heterocycle forming reactions. A tandem C-N/Suzuki coupling of a gemdihalovinylaniline and organoboron reagents including aryl, heteroaryl, alkenylboronic acids (or borate esters) and alkyl boranes afforded a variety of 2-substituted indoles in good to excellent yield. This new method of indole synthesis tolerated various functional groups on all positions of the indole moiety. The orthogonal approach of the sequential copper and palladium-mediated synthesis of 1,2-diarylindoles exploited the availability of diverse organoboron reagents. This new method was successfully applied for the synthesis of three Merck KDR kinase inhibitors in very good overall yields. The Pd-catalyzed tandem couplings of gemdihalovinyl systems were further extended for the synthesis of (1) 2-carbonyl indoles via a C-N coupling, carbonylation, and Suzuki sequence, (2) 2-vinyl indoles via a C-N coupling/Heck reaction sequence, and (3) 2 alkynyl indoles via a C-N/Sonogashira coupling sequence. Furthermore, a Cu-catalyzed tandem Goldberg reaction was developed for the synthesis of imidazoindolones from amino acid-tethered gemdibromoolefins. Preliminary studies towards a modular synthesis of azaindoles from N'-Boc- N'-gemdibromovinyl pyridylamine via a sequential Suzuki/direct arylation protocol was also explored. This new tandem coupling reaction was also successfully extended to two other pharmaceutically important families of heterocycles, azaindoles and thienopyrroles. Suitable substituents (such as alkyl, Boc, and Cbz) on the amino group of the substrate were essential to prevent catalyst poisoning during the tandem process.
Download or read book The Mizoroki Heck Reaction written by Martin Oestreich and published by John Wiley & Sons. This book was released on 2009-02-11 with total page 608 pages. Available in PDF, EPUB and Kindle. Book excerpt: Exploring the importance of Richard F. Heck’s carbon coupling reaction, this book highlights the subject of the 2010 Nobel Prize in Chemistry for palladium-catalyzed cross couplings in organic synthesis, and includes a foreword from Nobel Prize winner Richard F. Heck. The Mizoroki-Heck reaction is a palladium-catalyzed carbon–carbon bond forming process which is widely used in organic and organometallic synthesis. It has seen increasing use in the past decade as chemists look for strategies enabling the controlled construction of complex carbon skeletons. The Mizoroki-Heck Reaction is the first dedicated volume on this important reaction, including topics on: mechanisms of the Mizoroki-Heck reaction intermolecular Mizoroki-Heck reactions focus on regioselectivity and product outcome in organic synthesis waste-minimized Mizoroki-Heck reactions intramolecular Mizoroki-Heck reactions formation of heterocycles chelation-controlled Mizoroki-Heck reactions the Mizoroki-Heck reaction in domino processes oxidative heck-type reactions (Fujiwara-Moritani reactions) Mizoroki-Heck reactions with metals other than palladium ligand design for intermolecular asymmetric Mizoroki-Heck reactions intramolecular enantioselective Mizoroki-Heck reactions desymmetrizing Mizoroki-Heck reactions applications in combinatorial and solid phase syntheses, and the development of modern solvent systems and reaction techniques the asymmetric intramolecular Mizoroki-Heck reaction in natural product total synthesis Several chapters are devoted to asymmetric Heck reactions with particular focus on the construction of otherwise difficult-to-obtain sterically congested tertiary and quaternary carbons. Industrial and academic applications are highlighted in the final section. The Mizoroki-Heck Reaction will find a place on the bookshelves of any organic or organometallic chemist. “I am convinced that this book will rapidly become the most important reference text for research chemists in academia and industry who seek orientation in the rapidly growing and – for the layman – confusing field described as the “’Mizoroki–Heck reaction’.” (Synthesis, March 2010)
Download or read book Synthesis of Aromatic Heterocycles and Carbocycles Through Tandem Palladium Catalyzed Cross Coupling Reactions of Gem dihaloolefins written by Christopher Scott Bryan and published by . This book was released on 2010 with total page 798 pages. Available in PDF, EPUB and Kindle. Book excerpt: Our group has developed a strategy for the synthesis of benzofused carbocycles and heterocycles through tandem palladium-catalyzed reactions of gem-dibromoolefins. In these syntheses, one bromide undergoes a Pd-catalyzed cyclization reaction, and the other participates in an orthogonal inter- or intramolecular Pd-catalyzed reaction to functionalize or annulate that ring, respectively.Chapter 2 describes the synthesis of benzothiophenes through the combination of a Pd-catalyzed C--S coupling with an orthogonal Suzuki, Heck, or Sonogashira reaction. This represents the first example of the incorporation of Pd-catalyzed C--S coupling into a tandem reaction.Chapter 1 describes the pairing of an intramolecular C--N bond forming reaction (the Buchwald- Hartwig coupling) with an intramolecular direct arylation for the synthesis of fused indole derivatives. A range of previously unknown heterocycles were synthesized through this method.In Chapter 3, a tandem intramolecular Heck / intermolecular Suzuki reaction is described for the synthesis of methyleneindenes. Studies on this reaction have provided advanced understanding of the mechanism, including how variation of the ligand controls the regioselectivity of the reaction.
Download or read book Palladium Catalyzed Coupling Reactions written by Árpád Molnár and published by John Wiley & Sons. This book was released on 2013-02-14 with total page 531 pages. Available in PDF, EPUB and Kindle. Book excerpt: This handbook and ready reference brings together all significant issues of practical importance in selected topics discussing recent significant achievements for interested readers in one single volume. While covering homogeneous and heterogeneous catalysis, the text is unique in focusing on such important aspects as using different reaction media, microwave techniques or catalyst recycling. It also provides a comprehensive treatment of key issues of modern-day coupling reactions having emerged and matured in recent years and emphasizes those topics that show potential for future development, such as continuous flow systems, water as a reaction medium, and catalyst immobilization, among others. With its inclusion of large-scale applications in the pharmaceutical industry, this will equally be of great interest to industrial chemists. From the contents * Palladium-Catalyzed Cross-Coupling Reactions - A General Introduction * High-turnover Heterogeneous Palladium Catalysts in Coupling Reactions: the Case of Pd Loaded on Dealuminated Y Zeolites Palladium-Catalyzed Coupling Reactions with Magnetically Separable Nanocatalysts * The Use of Ordered Porous Solids as Support Materials in Palladium-Catalyzed Cross-Coupling Reactions * Coupling Reactions Induced by Polymer-Supported Catalysts * Coupling Reactions in Ionic Liquids * Cross-Coupling Reactions in Aqueous Media * Microwave-Assisted Synthesis in C-C and C-Heteroatom Coupling Reactions * Catalyst Recycling in Palladium-Catalyzed Carbon-Carbon Coupling Reactions * Nature of the True Catalytic Species in Carbon-Carbon Coupling Reactions with * Heterogeneous Palladium Precatalysts * Coupling Reactions in Continuous Flow Systems * Large-Scale Applications of Palladium-Catalyzed Couplings in the Pharmaceutical Industry
Download or read book Palladium Assisted Synthesis of Heterocycles written by Navjeet Kaur and published by CRC Press. This book was released on 2019-05-01 with total page 482 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book is a compilation of the recent applications of palladium catalysts in organic synthesis. The book demonstrates that it is a highly dynamic research field. This methodology has emerged as a powerful tool for the efficient and chemoselective synthesis of heterocyclic molecules. In the past few years, several strategies have been pointed out to pursue more efficient, sustainable, and environment friendly chemical processes. Among those strategies, catalysis and the design of new processes that avoid the use of toxic reagents have been the focus of intense research.
Download or read book Palladium in Heterocyclic Chemistry written by Jie Jack Li and published by Elsevier. This book was released on 2006-10-20 with total page 662 pages. Available in PDF, EPUB and Kindle. Book excerpt: Palladium chemistry, despite its immaturity, has rapidly become an indispensable tool for synthetic organic chemists. Heterocycles are of paramount importance in the pharmaceutical industry and palladium chemistry is one of the most novel and efficient ways of making heterocycles. Today, palladium-catalyzed coupling is the method of choice for the synthesis of a wide range of biaryls and heterobiaryls. The number of applications of palladium chemistry to the syntheses of heterocycles has grown exponentially. These developments highlight the need for a monograph dedicated solely to the palladium chemistry in heterocycles and this book provides a comprehensive explanation of the subject. The principal aim of the book is to highlight important palladium-mediated reactions of heterocycles with emphasis on the unique characteristics of individual heterocycles. 1. Palladium chemistry of heterocycles has its “idiosyncrasies stemming from their different structural properties from the corresponding carbocyclic aryl compounds. Even activated chloroheterocycles are sufficiently reactive to undergo Pd-catalyzed reactions. As a consequence of &agr and &bgr activation of heteroaryl halides, Pd-catalyzed chemistry may take place regioselectively at the activated positions, a phenomenon rarely seen in carbocyclic aryl halides. In addition, another salient peculiarity in palladium chemistry of heterocycles is the so-called "heteroaryl Heck reaction". For instance, while intermolecular palladium-catalyzed arylations of carbocyclic arenes are rare, palladium-catalyzed arylations of azoles and many other heterocycles readily take place. Therefore, the principal aim of this book is to highlight important palladium-mediated reactions of heterocycles with emphasis on the unique characteristics of individual heterocycles. 2. A myriad of heterocycles are biologically active and therefore of paramount importance to medicinal and agricultural chemists. Many heterocycle-containing natural products (they are highlighted in boxes throughout the text) have elicited great interest from both academic and industrial research groups. Recognizing the similarities between the palladium chemistry of arenes and heteroarenes, a critical survey of the accomplishments in heterocyclic chemistry will keep readers abreast of such a fast-growing field. We also hope this book will spur more interest and inspire ideas in such an extremely useful area. This book comprises a compilation of important preparations of heteroaryl halides, boranes and stannanes for each heterocycle. The large body of data regarding palladium-mediated polymerization of heterocycles in material chemistry is not focused here; neither is coordination chemistry involving palladium and heterocycles. Many heterocycle-containing natural products (highlighted throughout the text) have elicited great interest from both academic and industrial research groups. Recognizing the similarities between the palladium chemistry of arenes and heteroarenes, a critical survey of the accomplishments in heterocyclic chemistry keeps readers abreast of this fast-growing field. It is also hoped that this book will stimulate more interest and inspire new ideas in this exciting area. Contains the most up-to-date developments in this fast-moving field Includes 3 new chapters Incorporates material from selected well-respected authors on heterocyclic chemistry
Download or read book Palladium in Heterocyclic Chemistry written by Jie Jack Li and published by Elsevier. This book was released on 2000 with total page 436 pages. Available in PDF, EPUB and Kindle. Book excerpt: For this text, Jack Li and Gordon Gribble have compiled an array of referenced examples of the use of palladium in heterocyclic chemistry.
Download or read book Heterocycles from Double Functionalized Arenes written by Xiao-Feng Wu and published by Royal Society of Chemistry. This book was released on 2015 with total page 315 pages. Available in PDF, EPUB and Kindle. Book excerpt: An introduction to transition metal catalyzed coupling reactions of double-functionalized arenes in heterocycle synthesis.
Download or read book Handbook of Organopalladium Chemistry for Organic Synthesis written by Ei-ichi Negishi and published by John Wiley & Sons. This book was released on 2003-11-24 with total page 1697 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organized to provide maximum utility to the bench synthetic chemist. The editor is well-known for his work in exploring, developing, and applying organopalladium chemistry. Contributors include over 24 world authorities in the field.
Download or read book Metal catalyzed Cross coupling Reactions written by François Diederich and published by John Wiley & Sons. This book was released on 2008-07-11 with total page 540 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbon-carbon bond forming reactions are arguably the most important processes in chemistry, as they represent key steps in the building of complex molecules from simple precursors. Among these reactions, metal-catalyzed cross-coupling reactions are extensively employed in a wide range of areas of preparative organic chemistry, ranging from the synthesis of complex natural products, to supramolecular chemistry, and materials science. In this work, a dozen internationally renowned experts and leaders in the field bring the reader up to date by documenting and critically analyzing current developments and uses of metal-catalyzed cross-coupling reactions. A particularly attractive and useful feature, that enhances the practical value of this monograph, is the inclusion of key synthetic protocols, in experimental format, chosen for broad utility and application. This practice-oriented book can offer the practitioner short cuts to ensure they remain up-to-date with the latest developments.
Download or read book Synthesis of Aromatic Heterocycles and Carbocycles Through Tandem Palladium catalyzed Cross couplings of Gem dihaloolefins written by Christopher Bryan and published by . This book was released on 2010 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
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.
Download or read book Cross Coupling and Heck Type Reactions 3 written by Mats Larhed and published by Thieme Chemistry. This book was released on 2013 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: In Science of Synthesis: Cross Coupling and Heck-Type Reactions, expert authors present and discuss the best and most reliable methods currently available for the formation of new carbon-carbon and carbon-heteroatom bonds using these reactions, highlighted with representative experimental procedures. Together, the three volumes of Cross Coupling and Heck-Type Reactions provide an extensive overview of the current state of the art in this field of central importance in modern chemistry, and are an invaluable resource for the practicing synthetic organic chemist. This volume provides comprehensive coverage of the different classes of Heck-type reactions. It describes the state-of-the-art developments in each area whilst critically evaluating the strengths and weaknesses of the different methods. In accordance with the growing demand for synthetic efficiency and practicality in organic synthesis, many of these newly developed Heck-type methods feature operationally convenient conditions, high catalytic efficiency, and high levels of chemical, regiochemical, and stereochemical control. Metal-catalyzed C-H functionalization has also been developed into a powerful tool for organic synthesis, providing for original C-C disconnections in retrosynthetic analysis and improving the overall efficiency of the desired transformations. This volume also summarizes the most important concepts and methods in this hot research area. This volume is part of a 3-volume set: Cross Coupling and Heck-Type Reactions Workbench Edition General information about Science of Synthesis
Download or read book Palladium and Nickel Catalyzed Transformations Forming Functionalized Heterocycles written by Hyung Yoon and published by Springer Nature. This book was released on 2020-09-02 with total page 236 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.
Download or read book Aromatic C sp2 H Dehydrogenative Coupling Reactions written by Bagher Eftekhari-Sis and published by CRC Press. This book was released on 2019-10-31 with total page 310 pages. Available in PDF, EPUB and Kindle. Book excerpt: This comprehensive text covers the research and development trends in the growing field of aromatic C–H dehydrogenative coupling reactions, leading to different types of heterocycles. The author provides answers to how these coupling reactions occur, what kinds of heterocycles are synthesized, and what their advantages are. The palladium-, rhodium-, iridium-, copper-, cobalt-, ruthenium-, and ferric-catalyzed aromatic C(sp2)–H dehydrogenative cross-coupling reactions are described in detail. A useful reference source for researchers and graduates in the field of heterocyclic chemistry and transition-metal-catalyzed dehydrogenative coupling reactions. Features: Comprehensive volume on the synthesis of benzo-heterocycles via aromatic C(sp2)–H bond activation. Heterocycles are of paramount importance to medicinal chemistry and drug discovery. Provides a comprehensive literature survey on the construction of heterocycles. Reaction procedures and mechanistic explanations are included, which will appeal to those in fine chemicals and pharmaceutical companies.
Download or read book Transition Metal Catalyzed Heterocycle Synthesis via C H Activation written by Xiao-Feng Wu and published by John Wiley & Sons. This book was released on 2016-03-07 with total page 596 pages. Available in PDF, EPUB and Kindle. Book excerpt: Reflecting the tremendous growth of this hot topic in recent years, this book covers C-H activation with a focus on heterocycle synthesis. As such, the text provides general mechanistic aspects and gives a comprehensive overview of catalytic reactions in the presence of palladium, rhodium, ruthenium, copper, iron, cobalt, and iridium. The chapters are organized according to the transition metal used and sub-divided by type of heterocycle formed to enable quick access to the synthetic route needed. Chapters on carbonylative synthesis of heterocycles and the application of C-H activation methodology to the synthesis of natural products are also included. Written by an outstanding team of authors, this is a valuable reference for researchers in academia and industry working in the field of organic synthesis, catalysis, natural product synthesis, pharmaceutical chemistry, and crop protection.
Download or read book Palladacycles written by Anant Kapdi and published by Elsevier. This book was released on 2019-06-14 with total page 420 pages. Available in PDF, EPUB and Kindle. Book excerpt: Palladacycles: Catalysis and Beyond provides an overview of recent research in palladacycles in catalysis for cross-coupling and similar reactions. In the quest for developing highly efficient and robust palladium-based catalysts for C-C bond formation via cross-coupling reactions, palladacycles have played a significant role. In recent years, they have found a wide variety of applications, ranging from catalysts for cross-coupling and related reactions, to their more recent application as anticancer agents. This book explores early examples of the use of palladacyclic complexes in catalysis employing azobenzene and hydrazobenzene as coordinating ligands. Its applications in processes such as selective reduction of alkenes, alkynes, or nitroalkanes are also covered. Palladacycles: Catalysis and Beyond reveals the tremendous advances that have taken place in the potential applications of palladacycles as versatile catalysts in academia and industry. It is a valuable resource for synthetic chemists, organometallic chemists, and chemical biologists. Reviews the importance and various applications of palladacycles in academic research and industry, including industrial scale applications Includes the impact of palladacycles on coupling reactions and potential applications as anticancer agents Features coverage of nano and colloidal catalysis via palladacyclic degradation
