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Carbon Carbon Bond Formation Via Catalytic Hydrogenation And Transfer Hydrogenation
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Book Synopsis Carbon-carbon Bond Formation Via Catalytic Hydrogenation and Transfer Hydrogenation by : Yu Lu
Download or read book Carbon-carbon Bond Formation Via Catalytic Hydrogenation and Transfer Hydrogenation written by Yu Lu and published by . This book was released on 2012 with total page 628 pages. Available in PDF, EPUB and Kindle. Book excerpt: Under the conditions of transfer hydrogenation employing ortho-cyclometallated iridium C,O-benzoate catalysts, two protocols of iterative chain elongation of 1,3-diols to furnish 1,3-polyols were developed. First, one-directional chain elongation employing mono-protected 1,3-diols as starting materials was achieved. In all cases, high levels of catalyst-directed enantioselectivity and diastereoselectivity were observed. Then, double asymmetric allylation of 1,n-glycols to deliver C2-symmetric adducts with exceptional level of enantioselectivity was devised. Iterative two-directional elongation of 1,3-diols to furnish 1,3-polyols with high level of catalyst-directed diastereoselectivity was then achieved. Implementation of this methodology and other hydrogenative C-C bond formations proved to be effective means for the preparation of a known bryostatin A-ring fragment and the total synthesis of bryostatin 7.
Book Synopsis Transition Metal-catalyzed Carbon-carbon Bond Formation Utilizing Transfer Hydrogenation by : Timothy Patrick Montgomery
Download or read book Transition Metal-catalyzed Carbon-carbon Bond Formation Utilizing Transfer Hydrogenation written by Timothy Patrick Montgomery and published by . This book was released on 2015 with total page 1092 pages. Available in PDF, EPUB and Kindle. Book excerpt: A central tenant of organic synthesis is the construction of carbon-carbon bonds. One of the traditional methods for carrying out such transformations is that of carbonyl addition. Unfortunately, traditional carbonyl addition chemistry suffers various drawbacks: preactivation, moisture sensitivity, and the generation of stoichiometric organometallic waste. The research presented in this dissertation focuses on the development of methods that make use of nucleophile-electrophile pairs generated in situ via transfer hydrogenation, which allow the formation of carbonyl or imine addition products from the alcohol or amine oxidation level; streamlining the construction of complex molecules from simple, readily available starting materials. Additionally, studies toward the total synthesis of the fibrinogen receptor inhibitor tetrafibricin, utilizing the methods developed in catalytic carbon-carbon bond formation through the addition, transfer or removal of hydrogen, are presented.
Book Synopsis Transition Metal-catalyzed Reductive C-C Bond Formation Under Hydrogenation and Transfer Hydrogenation Conditions by : Ming-yu Ngai
Download or read book Transition Metal-catalyzed Reductive C-C Bond Formation Under Hydrogenation and Transfer Hydrogenation Conditions written by Ming-yu Ngai and published by . This book was released on 2008 with total page 652 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbon-carbon bond forming reactions are vital to the synthesis of natural products and pharmaceuticals. In 2003, the 200 best selling prescription drugs reported in Med Ad News are all organic compounds. Synthesizing these compounds involves many carbon-carbon bond forming processes, which are not trivial and typically generate large amounts of waste byproducts. Thus, development of an atom economical and environmentally benign carbon-carbon bond forming methodology is highly desirable. Hydrogenation is one of the most powerful catalytic reactions and has been utilized extensively in industry. Although carbon-carbon bond forming reactions under hydrogenation conditions, such as, alkene hydroformylation and the Fischer-Tropsch reaction are known, they are limited to the coupling of unsaturated hydrocarbons to carbon monoxide. Recently, a breakthrough was made by the Krische group, who demonstrated that catalytic hydrogenative C-C bond forming reactions can be extended to the coupling partners other than carbon monoxide. This discovery has led to the development of a new class of carbon-carbon bond forming reactions. Herein, an overview of transition metal-catalyzed reductive couplings of [pi]-unsaturated systems employing various external reductants is summarized in Chapter 1. Chapters 2-4 describe a series of rhodium- and iridium-catalyzed asymmetric hydrogenative couplings of various alkynes to a wide range of imines and carbonyl compounds. These byproduct-free transformations provide a variety of optically enriched allylic amines and allylic alcohols, which are found in numerous natural products, and are used as versatile precursors for the synthesis of many biologically active compounds. Transfer hydrogenation represents another important class of reactions in organic chemistry. This process employs hydrogen sources other than gaseous dihydrogen, such as isopropanol. The Krische group succeeded in developing a new family of transfer hydrogenative carbon-carbon bond formation reactions. Chapter 5 presents two novel ruthenium- and iridium-catalyzed transfer hydrogenative carbonyl allylation reactions. The catalytic system employing iridium complexes enables highly enantioselective carbonyl allylation from both the alcohol and aldehyde oxidation level. These systems define a departure from the use of preformed organometallic reagents in carbonyl additions that transcends the boundaries of oxidation level.
Book Synopsis Development of Neutral Redox Carbon-carbon Bond Forming Reactions Via Transition Metal-catalyzed Transfer Hydrogenation by : Khoa Dang Nguyen (Ph. D.)
Download or read book Development of Neutral Redox Carbon-carbon Bond Forming Reactions Via Transition Metal-catalyzed Transfer Hydrogenation written by Khoa Dang Nguyen (Ph. D.) and published by . This book was released on 2017 with total page 1316 pages. Available in PDF, EPUB and Kindle. Book excerpt: Since C-C bonds form the backbone of every organic molecule and reside at the heart of chemical science, the development of new efficient methods for promoting C-C bond formation is of great significance. Inspired and expanded from traditional Grignard reactions, the work presented in this dissertation focuses on metal catalyzed neutral redox-triggered carbonyl addition via transfer hydrogenation. Advancing the native reducing capability of alcohols, employment of catalytic transition metals enables the formation of nucleophile-electrophile pairs in situ, en route to the products of formal alcohol C-H functionalization. These redox-triggered reactions circumvent the stoichiometric metallated byproduct waste and streamline the construction of complex molecules from simple and/or readily available feedstocks. The research reported herein discloses new developed methodologies of ruthenium and iridium catalyzed coupling reactions of primary and secondary alcohols with various pi-unsaturates. These studies contribute to the growing body of redox-triggered alcohol C-C couplings - new carbonyl addition chemistry that extends beyond the use of premetalated reagents.
Download or read book Hydrogenation written by Iyad Karamé and published by BoD – Books on Demand. This book was released on 2012-10-10 with total page 342 pages. Available in PDF, EPUB and Kindle. Book excerpt: The domain of catalytic hydrogenation continues to grow fast, reflecting the wide range of chemical applications that can be enhanced by the easy use of molecular hydrogen. The advances in characterization techniques and their application have improved our understanding of the catalytic processes and mechanisms occurring in both homogeneous and heterogeneous catalysis. The aim of this volume, although not exhaustive, is to provide a general overview of new progress of the hydrogenation reactions. This volume comprises a series of various contributions, as reviews or original articles, treating heterogeneously and homogeneously catalyzed hydrogenation reactions. It is composed of three parts: hydrogenation reactions in fine organic chemistry, hydrogenation reactions in environmental chemistry and renewable energy, and special topics in hydrogenation.
Book Synopsis New Advances in Hydrogenation Processes by : Maryam Takht Ravanchi
Download or read book New Advances in Hydrogenation Processes written by Maryam Takht Ravanchi and published by BoD – Books on Demand. This book was released on 2017-01-25 with total page 364 pages. Available in PDF, EPUB and Kindle. Book excerpt: Hydrogen is one of the abundant elements on earth majorly in the form of water (H2O) and mainly as hydrogen gas (H2). Catalytic hydrogenation is a key reaction that has versatile applications in different industries. The main objective of this book is to bring together various applications of hydrogenation through the perspective of leading researchers in the field. This book is intended to be used as a graduate-level text book or as a practical guide for industrial engineers.
Book Synopsis Catalytic Hydrogenation by : L. Cervený
Download or read book Catalytic Hydrogenation written by L. Cervený and published by Elsevier. This book was released on 1986-08-01 with total page 705 pages. Available in PDF, EPUB and Kindle. Book excerpt: The collection of contributions in this volume presents the most up-to-date findings in catalytic hydrogenation. The individual chapters have been written by 36 top specialists each of whom has achieved a remarkable depth of coverage when dealing with his particular topic. In addition to detailed treatment of the most recent problems connected with catalytic hydrogenations, the book also contains a number of previously unpublished results obtained either by the authors themselves or within the organizations to which they are affiliated.Because of its topical and original character, the book provides a wealth of information which will be invaluable not only to researchers and technicians dealing with hydrogenation, but also to all those concerned with homogeneous and heterogeneous catalysis, organic technology, petrochemistry and chemical engineering.
Book Synopsis Transition Metal Catalyzed Hydrogenative and Transfer Hydrogenative C-C Bond Formation by : Eduardas Skucas
Download or read book Transition Metal Catalyzed Hydrogenative and Transfer Hydrogenative C-C Bond Formation written by Eduardas Skucas and published by . This book was released on 2009 with total page 404 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbon-carbon bond formation is one the fundamental reactions in organic synthesis. The quest for the development of new and more efficient processes for the construction of this bond has been an ongoing focus for years. The transformations that permit the use of simple precursors to access complex structural architectures in the absence of stoichiometric quantities by-products are highly desirable. Hydrogen is a cheapest and cleanest reductant available to the mankind. The catalytic hydrogenation has been widely utilized in the industry, however the construction of the carbon-carbon bond under hydrogenative conditions has been achieved only for alkene hydroformylations and Fisher-Tropsh process and limited to the use of carbon monoxide. The extension of the hydrogenative carbon-carbon bond formations beyond aforementioned processes would be of a great significance to the synthetic community. The overview of allene use in the metal catalyzed reactions to achieve carbonyl and imine allylation and vinylation is presented in Chapter 1. The following chapter vii discusses the development of metal catalyzed hydrogenative and transfer hydrogenative coupling of allenes and carbonyl compounds to afford allylation products. These studies have resulted in the development of the first carbonyl allylation from the alcohol oxidation level. Chapter 3 discusses efforts towards achieving highly enantioselective hydrogenative coupling of alkynes to carbonyl compounds.
Book Synopsis Hydrogen Transfer Reactions by : Gabriela Guillena
Download or read book Hydrogen Transfer Reactions written by Gabriela Guillena and published by Springer. This book was released on 2016-09-27 with total page 393 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Current Chemistry Collections presents critical reviews from the journal Topics in Current Chemistry organized in topical volumes. 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.
Book Synopsis Transition Metal Catalyzed Regioselective Carbon-carbon Bond Formation Mediated by Transfer Hydrogenation by : Brannon Sam
Download or read book Transition Metal Catalyzed Regioselective Carbon-carbon Bond Formation Mediated by Transfer Hydrogenation written by Brannon Sam and published by . This book was released on 2015 with total page 1026 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Formation of C-C Bonds Via Transfer Hydrogenation by : Xin Gao
Download or read book Formation of C-C Bonds Via Transfer Hydrogenation written by Xin Gao and published by . This book was released on 2013 with total page 966 pages. Available in PDF, EPUB and Kindle. Book excerpt: Under the conditions of transfer hydrogenation employing ortho-cyclometallated iridium C,O-benzoate catalysts, selective silylallylation and CF3-allylation were developed. In both cases, high levels of catalyst-directed enantioselectivity and diastereoselectivity were observed. Column chromatography was then tested as a new protocol to purify the iridium precatalyst; this single component precatalyst was proved to be more efficient to promote carbonyl crotylation reactions, both diastereo- and enantioselectivity were increased. Then, double asymmetric crotylation of 1,3-diols to deliver (pseudo-)C2-symmetric adducts with exceptional level of enantioselectivity was devised. Implementation of this methodology and other hydrogenative C-C bond formations proved to be effective means for the preparation of two known polypropionate natural product fragments of C19-C25 of scytophycin C, C19-C27 of rifamycin S and the total synthesis of 6-deoxyerythronolide B.
Book Synopsis Transition Metal Catalyzed C-C Bond Formation Under Transfer Hydrogenation Conditions by : Joyce Chi Ching Leung
Download or read book Transition Metal Catalyzed C-C Bond Formation Under Transfer Hydrogenation Conditions written by Joyce Chi Ching Leung and published by . This book was released on 2013 with total page 902 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbon-carbon bond forming reactions are fundamental transformations for constructing structurally complex organic building blocks, especially in the realm of natural products synthesis. Classical protocols for forming a C-C bond typically require the use of stoichiometrically preformed organometallic reagents, constituting a major drawback for organic synthesis on process scale. Since the emergence of transition metal catalysis in hydrogenation and hydrogenative C-C coupling reactions, atom and step economy have become important considerations in the development of sustainable methods. In the Krische laboratory, our goal is to utilize abundant, renewable feedstocks, so that the reactions can proceed in an efficient and atom-economical manner. Our research focuses on developing new C-C bond forming protocols that transcend the use of stoichiometric, preformed organometallic reagents, in which [pi]-unsaturates can be employed as surrogates to discrete premetallated reagents. Under transition metal catalyzed transfer hydrogenation conditions, alcohols can engage in C-C coupling, avoiding unnecessary redox manipulations prior to carbonyl addition. Stereoselective variants of these reactions are also under extensive investigation to effect stereo-induction by way of chiral motifs found in ligands and counterions. The research presented in this dissertation represents the development of a new class of C-C bond forming transformations useful for constructing synthetic challenging molecules. Development of transfer hydrogenative C-C bond forming reactions in the form of carbonyl additions such as carbonyl allylation, carbonyl propargylation, carbonyl vinylation etc. are discussed in detail. Additionally, these methods avoid the use of stoichiometric chiral allenylmetal, propargylmetal or vinylmetal reagents, respectively, accessing diastereo- and enantioenriched products of carbonyl additions in the absence of stoichiometric organometallic byproducts. By exploiting the atom-economical transfer hydrogenative carbonyl addition protocols using ruthenium and iridium, preparations of important structural motifs that are abundant in natural products, such as allylic alcohols, homoallylic alcohols and homopropargylic alcohols, become more feasible and accessible.
Book Synopsis Hydrogen-mediated Carbon-carbon Bond Formations by : Susan Amy Garner
Download or read book Hydrogen-mediated Carbon-carbon Bond Formations written by Susan Amy Garner and published by . This book was released on 2007 with total page 556 pages. Available in PDF, EPUB and Kindle. Book excerpt: Hydrogen gas is the cleanest and most cost-effective reductant available to mankind, and the use of hydrogen gas in catalytic hydrogenation reactions is one of the oldest and most utilized organic reactions. Although catalytic hydrogenation has been practiced in industry on enormous scale, the use of hydrogen gas as a terminal reductant in C-C bond forming reactions has been limited to processes involving the migratory insertion of carbon monoxide such as: alkene hydroformylation and the Fischer-Tropsch reaction. A significant advance to the field of synthetic organic chemistry would be the expansion of C-C bond forming reactions beyond reductive coupling via carbon monoxide insertion. Herein, related metal catalyzed reductive couplings to [alpha], [beta]-unsaturated compounds in the presence of reducing agents such as: silane, borane, and hydrogen are reviewed. The following chapters discuss the development of hydrogen-mediated reductive aldol and Mannich reactions. The results from this body of work clearly demonstrate that hydrogen-mediated C-C bond forming reactions are emerging as a powerful tool for synthetic chemists.
Book Synopsis Surface Organometallic Chemistry: Molecular Approaches to Surface Catalysis by : Jean-Marie Basset
Download or read book Surface Organometallic Chemistry: Molecular Approaches to Surface Catalysis written by Jean-Marie Basset and published by Springer Science & Business Media. This book was released on 2012-12-06 with total page 340 pages. Available in PDF, EPUB and Kindle. Book excerpt: Surface organometallic chemistry is a new field bringing together researchers from organometallic, inorganic, and surface chemistry and catalysis. Topics ranging from reaction mechanisms to catalyst preparation are considered from a molecular basis, according to which the "active site" on a catalyst surface has a supra-molecular character. This. the first book on the subject, is the outcome of a NATO Workshop held in Le Rouret. France, in May. 1986. It is our hope that the following chapters and the concluding summary of recommendations for research may help to provide a definition of surface organometallic chemistry. Besides catalysis. the central theme of the Workshop, four main topics are considered: 1) Reactions of organometallics with surfaces of metal oxides, metals. and zeolites; 2) Molecular models of surfaces, metal oxides, and metals; 3) Molecular approaches to the mechanisms of surface reactions; 4) Synthesis and modification of zeolites and related microporous solids. Most surface organometallic chemistry has been carried out on amorphous high-surf ace-area metal oxides such as silica. alumina. magnesia, and titania. The first chapter. contributed by KNOZINGER. gives a short summary of the structure and reactivity of metal oxide surfaces. Most of our understanding of these surfaces is based on acid base and redox chemistry; this chemistry has developed from X-ray and spectroscopic data, and much has been inferred from the structures and reactivities of adsorbed organic probe molecules. There are major opportunities for extending this understanding by use of well-defined (single crystal) oxide surfaces and organometallic probe molecules.
Book Synopsis Catalytic Hydrogenation in Organic Synthesis by : Morris Freifelder
Download or read book Catalytic Hydrogenation in Organic Synthesis written by Morris Freifelder and published by John Wiley & Sons. This book was released on 1978-11 with total page 218 pages. Available in PDF, EPUB and Kindle. Book excerpt: Based on over 22 years of experience, this book presents a substantial accumulation of knowledge. Clearly and understandably written, it gives detailed descriptions of many experiments, providing step-by-step procedures along with personal notes and observations, directions, suggestions, and safety precautions. The yields obtained in these experiments are good to excellent, and most of the hydrogenations discussed are carried out under very mild conditions.
Book Synopsis Catalytic Hydrogenation in Organic Syntheses by : Rylander
Download or read book Catalytic Hydrogenation in Organic Syntheses written by Rylander and published by Elsevier. This book was released on 2012-12-02 with total page 336 pages. Available in PDF, EPUB and Kindle. Book excerpt: Catalytic Hydrogenation in Organic Syntheses focuses on the process of catalytic hydrogenation in organic synthesis. This book gives the reader easy access to catalytic history, to show what can be done and how to do it. A variety of working generalities and common sense guides are given as aids in selecting catalytic metal, catalyst support, concentration of metal and catalyst, solvent, and reaction conditions. All manner of hydrogenation catalysts are considered and mechanisms of hydrogenation are presented at a level that is useful to the synthetic organic chemist. This volume is comprised of 15 chapters and begins with an overview of catalytic hydrogenation and heterogeneous hydrogenation catalysts, along with hydrogenation reactors and reaction conditions. The discussion then shifts to the hydrogenation of compounds such as acetylenes, olefins, aldehydes, ketones, nitriles, oximes, acids, esters, lactones, anhydrides, and nitro compounds as well as carbocyclic aromatics and heterocyclic compounds. The reader is also introduced to reductive alkylation, catalytic dehydrohalogenation, and hydrogenolysis of small rings. A chapter on miscellaneous hydrogenolyses concludes the book. This book will be of interest to organic chemists working in the field of catalytic hydrogenation.
Book Synopsis Catalytic Hydrogenation for Biomass Valorization by : Roberto Rinaldi
Download or read book Catalytic Hydrogenation for Biomass Valorization written by Roberto Rinaldi and published by Royal Society of Chemistry. This book was released on 2015 with total page 324 pages. Available in PDF, EPUB and Kindle. Book excerpt: As the biorefinery industry expands to meet the latest discoveries in biomass conversion, this book provides a thorough grounding in the subject.
