Download or read book New Palladium Catalysed Intramolecular Coupling Reactions written by Francesco Mariani and published by . This book was released on 2016 with total page 200 pages. Available in PDF, EPUB and Kindle. Book excerpt: Although sygma-aryl and sygma-vinylpalladium(II) complexes are commonly used as electrophiles in C--C bond forming reactions, recent research has demonstrated that the same palladium intermediates can also react with carbon-heteroatom multiple bonds in a nucleophilic manner. Continuing with the interest of our group on the palladium-catalysed intramolecular coupling of aryl halides whit carbonyl compounds, we have expanded our previous findings to substrates containing other carbon-heteroatom multiple bonds. In this context, the first objective of the PhD Thesis has been the study of the dual nature of the sygma-arylpalladium(II) species in aldehyde containing compounds. Thus, after some preliminary studies on the ambiphilic character of the sygma-arylpalladium(II) intermediates involved in the palladium-catalysed intramolecular reactions of (2-iodoanilino)-aldehydes, we have described an efficient new methodology for the synthesis of dibenzo[b, e]azepin-11-ones based on the intramolecular acylation of aryl iodides with aldehydes. Continuing whit our interest in these nucleophilic addition processes, we have developed an efficient methodology for the preparation of a small library of tetrahydroisoquinolin-4-ols based on the palladium-catalysed intramolecular nucleophilic addition of a-(2-iodobenzylamino)- aldehydes. Finally, we have expanded the influence of the heteroatom (nitrogen, oxygen, and sulphur) on the course of the palladium-catalysed intramolecular reactions of aryl iodides and aldehydes having heteroatom--containing tethers. Through an extensive experimental-computational (DFT) study we have concluded that the nature of the heteroatom in the tether is not decisive for the outcome of these reactions. Continuing our research for methodologies that help us to increase the synthetic potential of organopalladium chemistry, we decide to investigate the feasibility of the palladium-catalysed intramolecular coupling of aryl halides and diazoderivatives as a methodology for the synthesis of nitrogen heterocycles. So, the second objective was the study of the Pd-catalysed intramolecular coupling of aryl halides with N-tosylhydrazones and sygma-diazoesters in nitrogen containing substrates. We have found that palladium can be used to catalyse the C(sp3)-H insertion of metal carbenoids derived from sygma-diazoesters to form pyrrolidines through intramolecular assembly of C(sp3)-C(sp3) bonds. This reaction is the first example of palladium-catalyzed C(sp3)-C(sp3) bond assembly starting from diazocarbonyl compounds. The coupling reaction can be catalyzed by both Pd(0) and Pd(II), is regioselective, and shows a broad functional group tolerance.
Download or read book Cross Coupling Reactions written by Norio Miyaura and published by Springer. This book was released on 2003-07-01 with total page 253 pages. Available in PDF, EPUB and Kindle. Book excerpt: In 1972, a very powerful catalytic cycle for carbon-carbon bond formation was 2 first discovered by the coupling reaction of Grignard reagents at the sp -carbon. Over the past 30 years, the protocol has been substantially improved and expanded to other coupling reactions of Li,B,N,O,Al,Si,P,S,Cu,Mn,Zn,In,Sn, and Hg compounds. These reactions provided an indispensable and simple methodology for preparative organic chemists. Due to the simplicity and rel- bility in the carbon-carbon, carbon-heteroatom, and carbon-metalloid bo- formations,as well as high efficiency of the catalytic process,the reactions have been widely employed by organic chemists in various fields. Application of the protocol ranges from various syntheses of complex natural products to the preparation of biologically relevant molecules including drugs, and of sup- molecules, and to functional materials. The reactions on solid surfaces allow robot synthesis and combinatorial synthesis. Now, many organic chemists do not hesitate to use transition metal complexes for the transformation of org- ic molecules. Indeed, innumerable organic syntheses have been realized by the catalyzed reactions of transition metal complexes that are not achievable by t- ditional synthetic methods. Among these, the metal-catalyzed cross-coupling reactions have undoubtedly contributed greatly to the development of such a new area of “metal-catalyzed organic syntheses”. An excellent monograph for the cross-coupling reactions and other met- catalyzed C-C bond-forming reactions recently appeared in Metal-catalyzed Cross-coupling Reactions (Wiley-VCH,1998).
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 Metal Catalyzed Cross Coupling Reactions and More written by Armin de Meijere and published by John Wiley & Sons. This book was released on 2013-12-04 with total page 1640 pages. Available in PDF, EPUB and Kindle. Book excerpt: This three volume book is the follow-up handbook to the bestselling volume "Metal-Catalyzed Cross-Coupling Reactions", the definitive reference in the field. In line with the enormous developments in this area, this is not a new edition, but rather a new book in three volumes with over 50% more content. This new content includes C-H activation, shifting the focus away from typical cross-coupling reactions, while those topics and chapters found in de Meijere/Diederich's book have been updated and expanded. With its highly experienced editor team and the list of authors reading like an international Who's-Who in the field, this work will be of great interest to every synthetic chemist working in academia and industry.
Download or read book Catalyst Components for Coupling Reactions written by Gary A. Molander and published by John Wiley & Sons. This book was released on 2013-05-30 with total page 1749 pages. Available in PDF, EPUB and Kindle. Book excerpt: The long awaited Handbook for all synthetic chemists working on coupling reactions, compiling all major catalyst components in use in the area. Consists of a compilation of articles taken from the EROS database, with the inclusion of about 20 newly commissioned catalysts/pre-catalysts/ligands that have made an impact in this area of synthetic organic chemistry. Includes catalyst systems used in Heck, Kumada-Tamao-Corriu, Suzuki-Miyaura, Hiyama-Hatanaka, Negishi, Migita-Kosugi-Stille, Buchwald-Hartwig, and Tsuji-Trost coupling reactions.
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 Development and Application of Palladium catalyzed Carbon nitrogen Bond Forming Reactions written by Seble-Hiwot Teshome Wagaw and published by . This book was released on 1999 with total page 280 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book New Trends in Cross Coupling written by Thomas Colacot and published by Royal Society of Chemistry. This book was released on 2015 with total page 914 pages. Available in PDF, EPUB and Kindle. Book excerpt: Following on from its recognition in the 2010 Nobel Prize for Chemistry, contributors from across the globe present the latest cross-coupling trends in both academia and industry.
Download or read book Palladium catalyzed Intramolecular Coupling Reactions Between Aryl and Vinyl Iodides and Allylic Moieties written by Sharon Husak and published by . This book was released on 2007 with total page 142 pages. Available in PDF, EPUB and Kindle. Book excerpt: The effect of changing the allylic group in a palladium-catalyzed direct cross-coupling between aryl halides and allylic moieties was examined. beta-Heteroatom elimination was found to preferentially occur over beta-hydride elimination for substrates possessing an allylic moiety containing a good leaving group. Extension of the reaction conditions to the intramolecular coupling of aryl iodides and allylic alcohols allows for the rapid synthesis of a variety of carbo- and herterocycles containing aldehyde functionalities in good to excellent yields. Optimization of the palladium-catalyzed cross-coupling reaction between a vinyl halide and allyl carbonate allowed for the efficient synthesis of six-membered nitrogen-containing cycles. The nature of the leaving group strongly influences the yield of the coupling reaction. Application of the optimized conditions to the intramolecular cyclization of a vinyl iodide and allylic alcohol indicates the utility of this methodology in the formation of carbonyl-containing heterocycles.
Download or read book Cross coupling Reactions written by Joffrey Vrijdag and published by . This book was released on 2020 with total page 268 pages. Available in PDF, EPUB and Kindle. Book excerpt: "Cross-Coupling Reactions: An Overview opens with an overview of the fundamentals and applications of the young and fast developing area of transition metal catalyzed/mediated oxidative (dehydrogenative) C-H/C-H coupling reactions between two (hetero)arenes. Continuing, the authors highlight the recent advances regarding the ligand supported transition metal-catalyzed domino (cascade) or one-pot syntheses of various heterocycles involving cross-coupling reactions. The recent advances in Cu catalyzed tandem reactions for heterocycle synthesis are also addressed. Cu metal chemistry has garnered attention as a potential alternative to precious transition metals, being cheaper, more sustainable and more easily available. A comprehensive account of research on green chemical routes is provided, involving various palladium metal-based catalysts utilized in facilitating cross-coupling reaction in aqueous media. Reported decarboxylative cross-coupling reactions are discussed along with suitable examples, focusing on their mechanism of action"--
Download or read book Transition Metal Catalyzed Oxidative Cross Coupling Reactions written by Aiwen Lei and published by Springer. This book was released on 2018-12-14 with total page 192 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.
Download or read book Advances in Cross Coupling Reactions written by José Pérez Sestelo and published by MDPI. This book was released on 2020-12-03 with total page 234 pages. Available in PDF, EPUB and Kindle. Book excerpt: In this Special Issue, recent advances in cross-coupling reactions are presented in the form of original research articles, reviews, and short communications. These contributions cover different topics in this area, including novel coupling reactions, reaction conditions, synthetic alternatives, metal ligands, and applications for new pharmaceutical compounds and organic materials. In particular, the reviews deal with methodologies such as the synthesis of diarylketones through palladium catalysis and the most relevant examples of Suzuki–Miyaura and Buchwald–Hartwig coupling reactions in the synthesis of bioactive compounds. The synthetic utility of cross-coupling reactions for the synthesis of medium-size rings and the utility of Stille and Suzuki coupling reactions for the synthesis of new molecular machines based on sterically hindered anthracenyl trypticenyl units are also summarized. The original research articles present the synthesis of 2-alkynylpyrrols by inverse Sonogashira coupling and the synthesis of indoles under oxidative dearomative cross-dehydrogenative conditions. The efficient combination of iridium-catalyzed C–H borylation of aryl halides with the Sonogashira coupling and a sequential iridium-catalyzed borylation of NH-free pyrroles followed by a Suzuki–Miyaura reaction are included. The synthesis of aryl propionic acids, a common structural motif in medicinal chemistry, and the synthesis of new organic dyes are also covered.
Download or read book Practical Medicinal Chemistry with Macrocycles written by Eric Marsault and published by John Wiley & Sons. This book was released on 2017-09-12 with total page 617 pages. Available in PDF, EPUB and Kindle. Book excerpt: Including case studies of macrocyclic marketed drugs and macrocycles in drug development, this book helps medicinal chemists deal with the synthetic and conceptual challenges of macrocycles in drug discovery efforts. Provides needed background to build a program in macrocycle drug discovery –design criteria, macrocycle profiles, applications, and limitations Features chapters contributed from leading international figures involved in macrocyclic drug discovery efforts Covers design criteria, typical profile of current macrocycles, applications, and limitations
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 Hypervalent Iodine Chemistry written by Viktor V. Zhdankin and published by John Wiley & Sons. This book was released on 2013-10-01 with total page 630 pages. Available in PDF, EPUB and Kindle. Book excerpt: Hypervalent Iodine Chemistry is the first comprehensive text covering all of the main aspects of the chemistry of organic and inorganic polyvalent iodine compounds, including applications in chemical research, medicine, and industry. Providing a comprehensive overview of the preparation, properties, and synthetic applications of this important class of reagents, the text is presented in the following way: The introductory chapter provides a historical background and describes the general classification of iodine compounds, nomenclature, hypervalent bonding, structural features, and the principles of reactivity of polyvalent iodine compounds. Chapter 2 gives a detailed description of the preparative methods and structural features of all known classes of organic and inorganic derivatives of polyvalent iodine. Chapter 3, the key chapter of the book, deals with the many applications of hypervalent iodine reagents in organic synthesis. Chapter 4 describes the most recent achievements in hypervalent iodine catalysis. Chapter 5 deals with recyclable polymer-supported and nonpolymeric hypervalent iodine reagents. Chapter 6 covers the "green" reactions of hypervalent iodine reagents under solvent-free conditions or in aqueous solutions. The final chapter provides an overview of the important practical applications of polyvalent iodine compounds in medicine and industry. This book is aimed at all chemists interested in iodine compounds, including academic and industrial researchers in inorganic, organic, physical, medicinal, and biological chemistry. It will be particularly useful to synthetic organic and inorganic chemists, including graduate and advanced undergraduate students. It comprehensively covers the green chemistry aspects of hypervalent iodine chemistry, making it especially useful for industrial chemists.
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)
