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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 956 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 308 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 Modern Gold Catalyzed Synthesis by : A. Stephen K. Hashmi
Download or read book Modern Gold Catalyzed Synthesis written by A. Stephen K. Hashmi and published by John Wiley & Sons. This book was released on 2012-05-21 with total page 419 pages. Available in PDF, EPUB and Kindle. Book excerpt: With its impressive features, gold has led to completely new reaction types in recent years, which in turn have strongly influenced both organic catalysis and material science. Other fields where a significant amount of new results has been obtained include nanotechnology, self assembly/supramolecular systems and biochemical/medicinal chemistry. As a result, gold is one of the hottest topics in catalysis at the moment, with an increasing amount of research being carried out in this field. While focusing on homogeneous catalysis, this monograph also covers the main applications in heterogeneous catalysis. Following a look at the gold-catalyzed addition of heteroatom nucleophiles to alkynes, it goes on to discuss gold-catalyzed additions to allenes and alkenes, gold-catalyzed benzannulations, cycloisomerization and rearrangement reactions, as well as oxidation and reduction reactions. The whole is finished off with a section on gold-catalyzed aldol and related reactions and the application of gold-catalyzed reactions to natural product synthesis. Of interest to synthetic chemists and inorganic chemists, as well as organic chemists working in homogeneous catalysis, physical and technical chemists.
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 Silver in Organic Chemistry by : Michael Harmata
Download or read book Silver in Organic Chemistry written by Michael Harmata and published by John Wiley & Sons. This book was released on 2011-01-11 with total page 395 pages. Available in PDF, EPUB and Kindle. Book excerpt: The first authoritative book on using silver cations in organic chemistry—for catalysis and more! With more sophisticated catalytic methodologies fueling a resurgence in the study of cation-based chemistry, gold and platinum have stepped to the fore as the unique agents used to create new chemical reactions. Although these metals have become a primary focus of researchers in the field, another coinage metal that is often overlooked—but is as powerful as the others—is silver, a far less costly alternative to gold and platinum in aiding the development of new reactions. Making a strong case for the use of silver as a catalyst and structural element in organometal constructs, this authoritative book is the first to explore the benefits of using silver in organic chemistry by taking a close look at silver’s unique reactivity and structural characteristics for the development of new methods and materials. Silver in Organic Chemistry is: The first book to address catalysis using silver, whose use in organic chemistry is on the verge of exploding A resource for researchers wishing to do chemistry with silver cations, an area that stands in the shadow of gold chemistry, but still glistens, demonstrating that all that glitters is not gold—sometimes it’s silver! A guide for “first attempts” in working with silver cations Edited by a very well-respected, highly visible authority in this field Silver in Organic Chemistry promotes further scientific discussion by offering important new ways to examine the future possibilities of an emerging field. By elevating the importance of silver chemistry, this thought-provoking guide illustrates how this versatile metal can become an increasingly significant player in opening the door to new catalytic organic reactions and new organometal materials.
Book Synopsis Transition-Metal-Mediated Aromatic Ring Construction by : Ken Tanaka
Download or read book Transition-Metal-Mediated Aromatic Ring Construction written by Ken Tanaka and published by John Wiley & Sons. This book was released on 2013-07-09 with total page 785 pages. Available in PDF, EPUB and Kindle. Book excerpt: State-of-the-science methods, synthetic routes, and strategies to construct aromatic rings The development of new reactions for the synthesis of aromatic compounds is a highly active research area in organic synthesis, providing new functional organic materials, functional reagents, and biologically active compounds. Recently, significant advances in transition-metal-mediated reactions have enabled the efficient and practical construction of new aromatic rings with useful properties and applications. This book draws together and reviews all the latest discoveries and methods in transition-metal-mediated reactions, offering readers promising new routes to design and construct complex aromatic compounds. Integrating metal catalysis with aromatic compound synthesis, Transition-Metal-Mediated Aromatic Ring Construction offers a practical guide to the methods, synthetic routes, and strategies for constructing aromatic compounds. The book's five parts examine: [2+2+2], [2+2+1], and related cycloaddition reactions [4+2], [3+2], and related cycloaddition reactions Electrocyclization reactions Coupling and addition reactions Other important transformations, including methathesis reactions and skeletal rearrangement reactions Edited by Ken Tanaka, an internationally recognized expert in the field of transition-metal catalysis, the book features authors who are leading pioneers and researchers in synthetic reactions. Their contributions reflect a thorough review and analysis of the literature as well as their own firsthand laboratory experience developing new aromatic compounds. All chapters end with a summary and outlook, setting forth new avenues of research and forecasting new discoveries. There are also references at the end of each chapter, guiding readers to important original research reports and reviews. In summary, Transition-Metal-Mediated Aromatic Ring Construction offers synthetic chemists a promising new avenue for the development of important new aromatic compounds with a broad range of applications.
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 Organic Synthesis Using Transition Metals by : Roderick Bates
Download or read book Organic Synthesis Using Transition Metals written by Roderick Bates and published by John Wiley & Sons. This book was released on 2012-04-30 with total page 5 pages. Available in PDF, EPUB and Kindle. Book excerpt: Transition metals open up new opportunities for synthesis, because their means of bonding and their reaction mechanisms differ from those of the elements of the s and p blocks. In the last two decades the subject has mushroomed - established reactions are seeing both technical improvements and increasing numbers of applications, and new reactions are being developed. The practicality of the subject is demonstrated by the large number of publications coming from the process development laboratories of pharmaceutical companies, and its importance is underlined by the fact that three Nobel prizes have been awarded for discoveries in this field in the 21st Century already. Organic Synthesis Using Transition Metals, 2nd Edition considers the ways in which transition metals, as catalysts and reagents, can be used in organic synthesis, both for pharmaceutical compounds and for natural products. It concentrates on the bond-forming reactions that set transition metal chemistry apart from "classical" organic chemistry. Each chapter is extensively referenced and provides a convenient point of entry to the research literature. Topics covered include: introduction to transition metals in organic synthesis coupling reactions C-H activation carbonylative coupling reactions alkene and alkyne insertion reactions electrophilic alkene and alkyne complexes reactions of alkyne complexes carbene complexes h3- or p-allyl -allyl complexes diene, dienyl and arene complexes cycloaddition and cycloisomerisation reactions For this second edition the text has been extensively revised and expanded to reflect the significant improvements and advances in the field since the first edition, as well as the large number of new transition metal-catalysed processes that have come to prominence in the last 10 years – for example the extraordinary progress in coupling reactions using “designer” ligands, catalysis using gold complexes, new opportunities arising from metathesis chemistry, and C-H activation – without neglecting the well established chemistry of metals such as palladium. Organic Synthesis Using Transition Metals, 2nd Edition will find a place on the bookshelves of advanced undergraduates and postgraduates working in organic synthesis, catalysis, medicinal chemistry and drug discovery. It is also useful for practising researchers who want to refresh and enhance their knowledge of the field.
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 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 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
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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