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Rhodium Catalyzed Cycloadditions And Cycloisomerizations Involving Propargylic Esters And Alcohols
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Book Synopsis Rhodium-catalyzed Cycloadditions and Cycloisomerizations Involving Propargylic Esters and Alcohols by : Xiaoxun Li
Download or read book Rhodium-catalyzed Cycloadditions and Cycloisomerizations Involving Propargylic Esters and Alcohols written by Xiaoxun Li and published by . This book was released on 2014 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Transition metal-catalyzed cyloaddition and cycloisomerization reactions occupy a central position within the realm of organic synthesis. Research described in this thesis focuses on using propargylic esters and alcohols as building blocks for rhodium(I)-catalyzed cycloadditions and cycloisomerizations. The discovery and application of combining the [pi]-acidity and redox/insertion reactivity of rhodium(I) complexes, led to the development of many new reactions. By taking advantage of Rh-catalyzed 1,3-acyloxy migration of propargylic esters, I developed two tandem reactions. One is Rh-catalyzed carbonylation of 3-acyloxy-1,4-enynes (ACEs) for the synthesis of highly substituted cyclopentenones, and the other is ring expansion of cyclopropanes or cyclobutanes for the preparation of highly functionalized seven-membered or eight-membered carbocycles. By taking advantage of Rh-catalyzed 1,2-acyloxy migration of propargylic esters adjacent to heterocycles, I developed a novel and practical method for the preparation of a series of heterocycles including indoles, benzofurans, carbazoles and benzothiophenes from substituted pyrroles, furans, indoles and thiophenes. Inspired by the first Rh-catalyzed intra- and intermolecular [5+2] cycloadditions of 3-acyloxy-1,4-enynes (ACEs) with alkynes, I developed a new five-carbon building block, an inverted ACE, for [5+2] cycloadditions by switching the position of the alkene and alkyne groups in ACE. By replacing the acyloxy group in ACE with OH leaving group and aniline nucleophile, a completely new type of 5-carbon building block (HYE) was designed for cycloadditions. The tandem indole annulation and [5+1] cycloaddition was realized for the synthesis of various highly substituted carbazoles. Natural products glycosinine and mahanimbine were prepared. Furthermore, indolyl Rh(I)-carbene could be generated from 3-hydroxy-1,4-enyne (HYE) through a dehydration process. With different N-protecting group, I prepared dimeric indoles, cyclopropyl indoles, vinyl indoles and other interesting indole derivatives.
Book Synopsis Rhodium-catalyzed [5+1] and [5+2] Cycloadditions Using 1,4-enyne as the Five-carbon Component by : Wangze Song
Download or read book Rhodium-catalyzed [5+1] and [5+2] Cycloadditions Using 1,4-enyne as the Five-carbon Component written by Wangze Song and published by . This book was released on 2016 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Transition metal-catalyzed cycloaddition reaction is one of the most efficient ways to access ring systems and remains to be one of the most active areas in organic chemistry. The discovery of 3-acyloxy-1,4-enyne (ACE) and 3-hydroxy-1,4-enyne (HYE) as the five-carbon components has led to the development of various Rh-catalyzed [5+1] and [5+2] cycloadditions in our group. These novel methods offered efficient access to highly substituted six- and seven-membered carbocycles. I will present our progresses on the development, application and mechanistic studies of the following four [5+1] and [5+2] cycloadditions. 1) Using ACE bearing an electron-rich ester as the five-carbon component, a [5+1] cycloaddition was realized under mild conditions for the preparation of highly substituted phenols. 2) Based on our previous success on Rh-catalyzed intermolecular [5+2] cycloaddition of ACE and alkynes, a library of highly substituted tropones was successfully prepared by modifying the cycloheptatriene products derived from the [5+2] cycloaddition. 3) The scope of the Rh-catalyzed intramolecular [5+2] cycloaddition of ACE with alkenes was expanded and the Rh-catalyzed intramolecular [5+2] cycloaddition of ACE with allenes was developed for the synthesis of highly functionalized bicyclic 5-7 fused ring systems with multiple stereogenic centers. 4) Using HYE as the 5-carbon component, a [5+1] carbonylative benzannulation reaction was previously developed in our group for the synthesis of tricyclic carbazoles. The scope of this tandem reaction is now expanded to the synthesis of tetra- and even pentacyclic ring systems including furocarbazoles, thiophenocarbazole, pyrrolocarbazole, and indolocarbazole. Metal carbene intermediates are involved in most of these cycloadditions. The strategy of using propargylic esters and propargylic alcohols as the Rh(I) carbene precursor should have broad implications in transition metal catalysis and metal carbene chemistry.
Book Synopsis Rhodium and Platinum Catalyzed Cycloadditions from Propargylic Esters and Ethers by :
Download or read book Rhodium and Platinum Catalyzed Cycloadditions from Propargylic Esters and Ethers written by and published by . This book was released on 2013 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: The past decade has witnessed a "gold rush" due to the novel [tau tau]-acidity of gold. On the other hand, rhodium is well known for traditional organometallic reactivities such as oxidative addition, reductive elimination, and carbonylation, which makes rhodium widely utilized in industrial processes such as hydroformylation and Monsanto acetic acid synthesis. My Ph.D. research combines [tau tau]-acidity of rhodium with traditional reactivities of rhodium. In particular, we use [tau tau]-acidic Rh-complexes to activate propargylic esters and ethers for cycloadditions. Propargylic esters can undergo either 1,3- or 1,2-acyloxy migration in the presence of rhodium to form allenes and vinyl metal carbenes respectively. By taking advantage of the Rh-catalyzed 1,3-acyloxy migration, I developed a [5+1] cycloaddition starting from cyclopropyl propargylic esters. By taking advantage of Rh-catalyzed 1,2-acyloxy migration, I contributed to the synthesis of 7- and 8-membered rings starting from vinyl propargylic esters. Vinyl metal carbenes could also be obtained from propargylic esters tethered with a nucleophile. By employing either platinum or rhodium metal complexes, I developed a tandem indole annulation and [4+3] cycloaddition with dienes and furans involving vinyl metal carbene intermediates. Biologically interesting bisindoles were also synthesized through a similar indole annulation followed by intermolecular nucleophilic trap of external indoles.
Book Synopsis Studies of Rhodium-catalyzed [5+2] Cycloadditions and Their Applications in Organic Synthesis by : Craig Owen Husfeld
Download or read book Studies of Rhodium-catalyzed [5+2] Cycloadditions and Their Applications in Organic Synthesis written by Craig Owen Husfeld and published by . This book was released on 2001 with total page 744 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Carbon Dioxide and Organometallics by : Xiao-Bing Lu
Download or read book Carbon Dioxide and Organometallics written by Xiao-Bing Lu and published by Springer. This book was released on 2015-08-26 with total page 313 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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
Book Synopsis Progress in Heterocyclic Chemistry by : Gordon W. Gribble
Download or read book Progress in Heterocyclic Chemistry written by Gordon W. Gribble and published by Elsevier. This book was released on 2011-11-07 with total page 548 pages. Available in PDF, EPUB and Kindle. Book excerpt: Progress in Heterocyclic Chemistry (PHC) is an annual review series commissioned by the International Society of Heterocyclic Chemistry (ISHC). Volumes in the series contain both highlights of the previous year's literature on heterocyclic chemistry and articles on emerging topics of particular interest to heterocyclic chemists. The chapters in Volume 23 constitute a systematic survey of the important original material reported in the literature of heterocyclic chemistry in 2010. As with previous volumes in the series, Volume 23 apprises academic/industrial chemists and advanced students of developments in heterocyclic chemistry in a convenient format. Covers the heterocyclic literature published in 2010 Includes specialized reviews Features contributions from leading researchers in their fields
Book Synopsis C-H Activation for Asymmetric Synthesis by : Françoise Colobert
Download or read book C-H Activation for Asymmetric Synthesis written by Françoise Colobert and published by John Wiley & Sons. This book was released on 2019-11-11 with total page 294 pages. Available in PDF, EPUB and Kindle. Book excerpt: Provides, in one handbook, comprehensive coverage of one of the hottest topics in stereoselective chemistry Written by leading international authors in the field, this book introduces readers to C-H activation in asymmetric synthesis along with all of its facets. It presents stereoselective C-H functionalization with a broad coverage, from outer-sphere to inner-sphere C-H bond activation, and from the control of olefin geometry to the induction of point, planar and axial chirality. Moreover, methods wherein asymmetry is introduced either during the C-H activation or in a different elementary step are discussed. Presented in two parts?asymmetric activation of C(sp3)-H bonds and stereoselective synthesis implying activation of C(sp2)-H bonds?CH-Activation for Asymmetric Synthesis showcases the diversity of stereogenic elements, which can now be constructed by C-H activation methods. Chapters in Part 1 cover: C(sp3)-H bond insertion by metal carbenoids and nitrenoids; stereoselective C-C bond and C-N bond forming reactions through C(sp3)?H bond insertion of metal nitrenoids; enantioselective intra- and intermolecular couplings; and more. Part 2 looks at: C-H activation involved in stereodiscriminant step; planar chirality; diastereoselective formation of alkenes through C(sp2)?H bond activation; amongst other methods. -Covers one of the most rapidly developing fields in organic synthesis and catalysis -Clearly structured in two parts (activation of sp3- and activation of sp2-H bonds) -Edited by two leading experts in C-H activation in asymmetric synthesis CH-Activation for Asymmetric Synthesis will be of high interest to chemists in academia, as well as those in the pharmaceutical and agrochemical industry.
Book Synopsis Homogeneous Gold Catalysis by : LeGrande M. Slaughter
Download or read book Homogeneous Gold Catalysis written by LeGrande M. Slaughter and published by Springer. This book was released on 2015-03-30 with total page 292 pages. Available in PDF, EPUB and Kindle. Book excerpt: 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.
Book Synopsis Comprehensive Organometallic Chemistry III, Volume 3 by : D. M. P. Mingos
Download or read book Comprehensive Organometallic Chemistry III, Volume 3 written by D. M. P. Mingos and published by . This book was released on 2007 with total page 976 pages. Available in PDF, EPUB and Kindle. Book excerpt: Provides essential information for any chemist or technologist who needs to use or apply organometallic compounds. Provides a comprehensive overview of recent developments in the field and attempts to predict trends in the field over the next ten years.
Book Synopsis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis by : Montserrat Diéguez
Download or read book Artificial Metalloenzymes and MetalloDNAzymes in Catalysis written by Montserrat Diéguez and published by John Wiley & Sons. This book was released on 2018-02-21 with total page 1200 pages. Available in PDF, EPUB and Kindle. Book excerpt: An important reference for researchers in the field of metal-enzyme hybrid catalysis Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a comprehensive review of the most current strategies, developed over recent decades, for the design, synthesis, and optimization of these hybrid catalysts as well as material about their application. The contributors—noted experts in the field—present information on the preparation, characterization, and optimization of artificial metalloenzymes in a timely and authoritative manner. The authors present a thorough examination of this interesting new platform for catalysis that combines the excellent selective recognition/binding properties of enzymes with transition metal catalysts. The text includes information on the various applications of metal-enzyme hybrid catalysts for novel reactions, offers insights into the latest advances in the field, and contains an informative perspective on the future: Explores the development of artificial metalloenzymes, the modern and strongly evolving research field on the verge of industrial application Contains a comprehensive reference to the research area of metal-enzyme hybrid catalysis that has experienced tremendous growth in recent years Includes contributions from leading researchers in the field Shows how this new catalysis combines the selective recognition/binding properties of enzymes with transition metal catalysts Written for catalytic chemists, bioinorganic chemists, biochemists, and organic chemists, Artificial Metalloenzymes and MetalloDNAzymes in Catalysis offers a unique reference to the fundamentals, concepts, applications, and the most recent developments for more efficient and sustainable synthesis.
Book Synopsis Progress in Heterocyclic Chemistry by : Gordon Gribble
Download or read book Progress in Heterocyclic Chemistry written by Gordon Gribble and published by Elsevier. This book was released on 2011-09-22 with total page 548 pages. Available in PDF, EPUB and Kindle. Book excerpt: Progress in Heterocyclic Chemistry (PHC) is an annual review series commissioned by the International Society of Heterocyclic Chemistry (ISHC). Volumes in the series contain both highlights of the previous year’s literature on heterocyclic chemistry and articles on emerging topics of particular interest to heterocyclic chemists. The chapters in Volume 23 constitute a systematic survey of the important original material reported in the literature of heterocyclic chemistry in 2010. As with previous volumes in the series, Volume 23 apprises academic/industrial chemists and advanced students of developments in heterocyclic chemistry in a convenient format. Covers the heterocyclic literature published in 2010 Includes specialized reviews Features contributions from leading researchers in their fields
Book Synopsis Journal by : American Chemical Society
Download or read book Journal written by American Chemical Society and published by . This book was released on 2001 with total page 1320 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Side Reactions in Organic Synthesis by : Florencio Zaragoza Dörwald
Download or read book Side Reactions in Organic Synthesis written by Florencio Zaragoza Dörwald and published by John Wiley & Sons. This book was released on 2006-03-06 with total page 389 pages. Available in PDF, EPUB and Kindle. Book excerpt: Most syntheses in the chemical research laboratory fail and usually require several attempts before proceeding satisfactorily. Failed syntheses are not only discouraging and frustrating, but also cost a lot of time and money. Many failures may, however, be avoided by understanding the structure-reactivity relationship of organic compounds. This textbook highlights the competing processes and limitations of the most important reactions used in organic synthesis. By allowing chemists to quickly recognize potential problems this book will help to improve their efficiency and success-rate. A must for every graduate student but also for every chemist in industry and academia. Contents: 1 Organic Synthesis: General Remarks 2 Stereoelectronic Effects and Reactivity 3 The Stability of Organic Compounds 4 Aliphatic Nucleophilic Substitutions: Problematic Electrophiles 5 The Alkylation of Carbanions 6 The Alkylation of Heteroatoms 7 The Acylation of Heteroatoms 8 Palladium-Catalyzed C-C Bond Formation 9 Cyclizations 10 Monofunctionalization of Symmetric Difunctional Substrates
Download or read book Nitroalkanes written by Roberto Ballini and published by John Wiley & Sons. This book was released on 2021-01-07 with total page 320 pages. Available in PDF, EPUB and Kindle. Book excerpt: Discover a comprehensive exploration of recent progress in the preparation of nitroalkanes from two leading voices in the field Nitroalkanes: Synthesis, Reactivity, and Applications delivers a thorough summary of the importance of nitroalkanes in organic synthesis. The book covers their preparation, transformation into other functional groups, like carbonyls and amines, and their use in the formation of single carbon-carbon or double carbon-carbon bonds. The distinguished authors have included chapters on acyclic and cyclic alpha-nitro ketones as well as the synthesis of cyclopropanes and spiro ketals. The book provides treatments of the application of nitroalkanes for the synthesis of important heterocycles, poly-functionalized structures, natural products, and compounds of biological and pharmaceutical interest. A one-stop resource in a topic that hasn???t been fully addressed by any other book in decades, this book covers the most important synthetic routes toward nitroalkanes. Readers will also benefit from the inclusion of: A thorough introduction to the synthesis of nitroalkanes, as well as the transformation of the nitro group into other functionalities An exploration of the formation of C-C single bonds, C=C double bonds, and the breaking of C3C bonds from cyclic alpha-nitro ketones Discussions of acyclic alpha-nitro ketones, nitroalkanes as precursors of cyclopropanes, and the synthesis of spiro ketals An examination of the preparation and synthetic applications of 1,3-Dinitroalkanes Perfect for organic chemists, natural products chemists, and catalytic chemists, Nitroalkanes: Synthesis, Reactivity, and Applications will also earn a place in the libraries of medicinal chemists seeking a one-stop resource for the most recent developments in the preparation of nitroalkanes, their functionalization, and their applications.
Book Synopsis Stereoselective Synthesis by : Gary A. Molander
Download or read book Stereoselective Synthesis written by Gary A. Molander and published by Thieme Chemistry. This book was released on 2011 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbonyl and imino groups are two of the most integral functional groups employed in organic synthesis. Specific topics discussed: reduction, alkylation, alkenylation, and arylation of these groups, as well as asymmetric aldol, Mannich, and Morita-Bayliss-Hillman reactions. This volume is part of a 3-volume set: Science of Synthesis Stereoselective Synthesis Workbench Edition Further information about Stereoselective Synthesis (including sample pages and the table of contents)
Book Synopsis Palladium in Heterocyclic Chemistry by : Jie Jack Li
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 658 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
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 387 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.
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