Download or read book New Copper catalyzed Reactions of Organoboron and Organosilicon Compounds written by Aaron M. Whittaker and published by . This book was released on 2013 with total page 195 pages. Available in PDF, EPUB and Kindle. Book excerpt: Copper-catalyzed transformations such as allylic substitution, conjugate addition, and electrophilic amination have proven to be indispensable tools for the formation of carbon-carbon and carbon-heteroatom bonds. Nevertheless, the use of highly reactive organometallic reagents limits functional group compatibility of these reactions and can contribute to poor selectivity in certain cases. Presented herein are four reactions that address the above mentioned limitations by catalytically accessing aryl, alkenyl, and alkyl copper intermediates from mild transmetalation partners. Specifically, the use of organoborane and silane transmetalation partners in copper-catalyzed reactions resulted in high levels of chemoselectivity, stereoselectivity, and regioselectivity thus providing products that are unattainable with the traditional approaches. Chapter 1 will describe the use of arylboronic esters as transmetalation partners in a copper catalyzed allylic substitution reaction. The comparatively low reactivity of the arylboronic esters allowed the preferential formation of monoaryl copper intermediates while avoiding the formation of diaryl cuprates. As a result, high SN20́ø selectivity was observed in the allylic arylation, alkenylation, and alkylation reactions. Finally, the development of an enantioselective variant giving up to 70% ee will be described. Detailed in chapter 2 is a formal hydroamination of alkenes using copper catalysis. Complete anti-Markovnikov selectivity for the alkene substrates is achieved in one-pot by hydroboration followed by copper-catalyzed electrophilic amination. This methodology was applied to the synthesis of trialkyl amines in the presence of a variety of functional groups, and was used to alkylate heterocycles. Furthermore, while investigating the reaction mechanism, Unambiguous evidence of a stable alkyl copper intermediate was provided with the first X-ray crystal structure of such a species. An extension of the hydroamination methodology will then be described in chapter 3. Copper-catalyzed coupling of arylboronic esters with electrophilic O-benzoyl hydroxylamines provided access to 32 different N,N-disubstituted anilines and heteroaromatic amines. The products obtained in these reactions have unprecedented levels of steric hindrance, but are nevertheless synthesized under mild conditions and in high yield. Finally, in chapter 4, I will outline a new approach to catalytic hydrofunctionalization that was used to develop a selective semireduction of alkynes. Simply using a silane and an alcohol, both terminal and internal alkynes were reduced to the alkene with surprising chemoselectivity and complete stereoselectivity. Moreover, as little as 0.5 mol % of a copper catalyst can be used and no over-reduction was observed.
Download or read book Synthesis of Functionalized Organoboron Compounds Through Copper I Catalysis written by Koji Kubota and published by Springer. This book was released on 2017-06-27 with total page 222 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book describes state-of-the-art borylation chemistry using copper(I) catalysis. Enantioselective reactions are included to afford a variety of functionalized, complex organoboronate esters, which will find wide application in asymmetric synthesis, drug discovery, and material science. Organoboron compounds are recognized as useful reagents in organic synthesis; therefore, great effort has been devoted to the development of a simple, mild, and efficient method for their preparation in the past several years. However, the synthesis of functionalized organoboron compounds remains a challenging issue because known reactions often require the use of highly reactive organometallic carbon nucleophiles. This book focuses on conceptually new, formal nucleophilic copper(I)-catalyzed borylation reactions with diboron compounds that show high selectivity and excellent functional group compatibility. Theoretical studies based on density functional theory calculations to understand the reaction mechanisms have also been described. Advances in this novel borylation chemistry will allow the rapid and efficient synthesis of complex molecules with potentially interesting properties in combination with the boron functionalization process.
Download or read book Copper catalyzed Reactions of Organoboron Compounds written by Richard P. Rucker and published by . This book was released on 2013 with total page 167 pages. Available in PDF, EPUB and Kindle. Book excerpt: The discovery, development, scope, and mechanistic studies of three new copper-catalyzed transformations of organoboron compounds are described herein. Specifically, Chapter 1 details the development and scope of the first general method for SN2'-selective substitution of primary allylic chlorides using aryl boronic esters as nucleophiles. The formal anti-Markovnikov hydroamination of 9-alkyl-9-BBN derivatives, which are conveniently prepared from the hydroboration of terminal alkenes, to give tertiary alkyl amines is discussed in Chapter 2. Chapter 3 describes the development, scope, and mechanistic studies of the copper-catalyzed electrophilic amination of aryl boronic esters and its application to the synthesis of hindered N,N-dialkyl anilines.
Download or read book Copper Catalysis in Organic Synthesis written by Gopinathan Anilkumar and published by John Wiley & Sons. This book was released on 2020-06-24 with total page 504 pages. Available in PDF, EPUB and Kindle. Book excerpt: The most current information on growing field of copper catalysis Copper Catalysis in Organic Synthesis contains an up-to-date overview of the most important reactions in the presence of copper catalysts. The contributors—noted experts on the topic—provide an introduction to the field of copper catalysis, reviewing its development, scope, and limitations, as well as providing descriptions of various homo- and cross-coupling reactions. In addition, information is presented on copper-catalyzed C–H activation, amination, carbonylation, trifluoromethylation, cyanation, and click reactions. Comprehensive in scope, the book also describes microwave-assisted and multi-component transformations as well as copper-catalyzed reactions in green solvents and continuous flow reactors. The authors highlight the application of copper catalysis in asymmetric synthesis and total synthesis of natural products and heterocycles as well as nanocatalysis. This important book: Examines copper and its use in organic synthesis as a more cost-effective and sustainable for researchers in academia and industry Offers the first up-to-date book to explore copper as a first line catalyst for many organic reactions Presents the most significant developments in the area, including cross-coupling reactions, C–H activation, asymmetric synthesis, and total synthesis of natural products and heterocycles Contains over 20 contributions from leaders in the field Written for catalytic chemists, organic chemists, natural products chemists, pharmaceutical chemists, and chemists in industry, Copper Catalysis in Organic Synthesis offers a book on the growing field of copper catalysis, covering cross-coupling reactions, C–H activation, and applications in the total synthesis of natural products.
Download or read book Copper I Catalyzed Stereoselective Borylation Reactions written by Yu Ozawa and published by Springer Nature. This book was released on 2023-05-30 with total page 236 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book focuses on the development of novel functionalized organoboron compounds and those synthetic methods. High degrees of chemo-, regio-, and stereoselectivities of the borylation reactions are attained through catalyst design and optimization. Furthermore, the selectivity-determining mechanisms are analyzed with state-of-the-art DFT and other computational methods. In this book, the author synthesizes some multi-substituted alkenyl and allylic boronates via borylation reactions using a copper(I)/diboron catalyst system. Those compounds contain novel densely substituted and distorted structures, which have not been accessed by other methods. The high stereoselectivities are achieved by the optimization of the catalyst, especially the ligand. Some new ligands are also developed in this book. Furthermore, the derivatization of the borylation products is demonstrated to access the sterically demanding complex molecules. Also, the author performs computational analysis to reveal how the catalyst controls the selectivities. The deep insight into the reaction mechanism provides guides for rational catalyst design for not only copper(I) catalysis but also other transition metal catalysis. Thus, the content should be of interest to academic and industrial scientists in a wide range of areas.
Download or read book Copper Mediated Cross Coupling Reactions written by Gwilherm Evano and published by John Wiley & Sons. This book was released on 2013-09-23 with total page 682 pages. Available in PDF, EPUB and Kindle. Book excerpt: Providing comprehensive insight into the use of copper in cross-coupling reactions, Copper-Mediated Cross-Coupling Reactions provides a complete up-to-date collection of the available reactions and catalytic systems for the formation of carbon-heteroatom and carbon-carbon bonds. This essential reference covers a broad scope of copper-mediated reactions, their variations, key advances, improvements, and an array of academic and industrial applications that have revolutionized the field of organic synthesis. The text also discusses the mechanism of these transformations, the use of copper as cost-efficient alternative to palladium, as well as recently developed methods for conducting copper-mediated reactions with supported catalysts.
Download or read book Boron bridged Bis oxazolines and Their Use in Copper catalyzed Reactions written by Aurélie Toussaint and published by Cuvillier Verlag. This book was released on 2008 with total page 271 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Copper Catalyzed Asymmetric Synthesis written by Alexandre Alexakis and published by John Wiley & Sons. This book was released on 2013-12-30 with total page 467 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book reflects the increasing interest among the chemical synthetic community in the area of asymmetric copper-catalyzed reactions, and introduces readers to the latest, most significant developments in the field. The contents are organized according to reaction type and cover mechanistic and spectroscopic aspects as well as applications in the synthesis of natural products. A whole chapter is devoted to understanding how primary organometallics interact with copper to provide selective catalysts for allylic substitution and conjugate addition, both of which are treated in separate chapters. Another is devoted to the variety of substrates and experimental protocols, while an entire chapter covers the use on non-carbon nucleophiles. Other chapters deal with less-known reactions, such as carbometallation or the additions to imines and related systems, while the more established reactions cyclopropanation and aziridination as well as the use of copper (II) Lewis acids are warranted their own special chapters. Two further chapters concern the processes involved, as determined by mechanistic studies. Finally, a whole chapter is devoted to the synthetic applications. This is essential reading for researchers at academic institutions and professionals at pharmaceutical or agrochemical companies.
Download or read book Copper in N Heterocyclic Chemistry written by Ananya Srivastava and published by Elsevier. This book was released on 2020-11-13 with total page 506 pages. Available in PDF, EPUB and Kindle. Book excerpt: Copper in N-Heterocyclic Chemistry provides an overview of copper-catalyzed synthesis and functionalization of N-heterocyclic compounds, covering all recent developments in a way that is ideal for researchers and students working in the area of synthetic organic chemistry and medicinal chemistry. The book explores N-heterocyclic compounds as unique structural units in the development of natural products and pharmaceuticals, along with the remarkable progress made in the area of high atom economic strategies, and more recently, copper-catalyzed C-H activation and its applications in organic synthesis. Readers will find troubleshooting protocols, as well as the advantages and limitations of each method discussed. As copper catalysts show versatile chemical reactivity in many aspects, including their oxidation states 0–3 are accessible and their ability to facilitate bond formations due to their ability to serve as Lewis acids, oxidizing agents and catalysts, this book is an ideal resource on the topics explored. Discusses novel synthetic methods developed over the past decade for copper-catalyzed synthesis of N-heterocyclic compounds Covers the most recent methodologies adapted in synthetic chemistry for applications in natural products and pharmaceuticals Includes troubleshooting protocols, as well as the advantages and limitations of each method discussed in detail
Download or read book Copper Catalysis written by Devendra Vyas and published by LAP Lambert Academic Publishing. This book was released on 2012-03 with total page 292 pages. Available in PDF, EPUB and Kindle. Book excerpt: The present work is devoted to the catalytic generation of silicon-based cuprates and their application in several C Si bond-forming reactions. A general procedure for the catalytic preparation of Cu Si nucleophiles via activation of Si B interelement linkages is described. This versatile copper(I)-catalyzed protocol involving formation of regioselective C Si bonds enables excess to a variety of organosilicon compounds. The detail investigations ascribing our preliminary attempts to transform into enantioselective variant in presence of different chiral ligands are also presented. In addition to this, the book also details on the study to explain the stereochemical surprises in reagent- controlled Lewis acid-mediated allylation of isatins with -chiral allylic stannane.
Download or read book Transition Metal catalyzed Reactions of Organoboron Compounds written by Yuri Bolshan and published by . This book was released on 2009 with total page 372 pages. Available in PDF, EPUB and Kindle. Book excerpt: This thesis describes research conducted since May 2003 at the University of Toronto in the laboratory of Professor Robert A. Batey. The manuscript is divided into three chapters. Chapter one provides a general introduction to the transition metal-catalyzed reactions of potassium organotrifluoroborate salts and methods for their preparation. A comparison in reactivity between organoboronic acids and organotrifluoroborate salts in metal-catalyzed reactions under similar reaction conditions and the importance of polar protic solvents during transmetalation step are also discussed.Chapter two provides an overview of the addition of organometallic and organometalloid reagents to imines. Particular attention is drawn to the metal-catalyzed additions of organozinc and organoboron compounds as well as the development of chiral ligands associated with these transformations. The synthesis, role and advantages of a chiral auxiliary over currently available methods in the synthesis of chiral amines are also described. In addition, chapter two provides a description of our contribution to this area of synthetic organic chemistry, including the synthesis of enantiomerically enriched amines via rhodium-catalyzed addition of arylboron compounds to N-tert-butanesulfinyl aldimines. The addition occurred at room temperature to afford the corresponding amides in good yields and high diastereoselectivities. The removal of the auxiliary is achieved under acidic conditions without detectable epimerization at a chiral center. The practical utility of this methodology was shown via the synthesis of a cetirizine precursor with high degree of diastereoselctivity.Chapter three introduces traditional and modern synthetic methods for the synthesis of the enamide functionality with an emphasis on palladium and copper-catalyzed transformations. The utility of enamides as synthetic intermediates in organic chemistry and their presence in natural products and biologically active compounds are also described. Our contribution to the field of enamide synthesis is discussed, including the optimization and scope of a novel copper-catalyzed cross-coupling between amides and potassium alkenyltrifluoroborate salts, which occurs under an atmosphere of oxygen in the presence of molecular sieves to afford enamides in good yields.
Download or read book The Chemistry of Organocopper Compounds written by Zvi Rappoport and published by John Wiley & Sons. This book was released on 2009-12-21 with total page 1183 pages. Available in PDF, EPUB and Kindle. Book excerpt: Copper in organic synthesis has seen a tremendous development over the past ten years. This text represents the most comprehensive survey on the use of Copper and Cuprates in organic synthesis. The first time that the Patai Series touches on Copper compounds, it contains contributions by leading experts, and delivers the quality expected from the Patai Series.
Download or read book Modern Organocopper Chemistry written by Norbert Krause and published by John Wiley & Sons. This book was released on 2002 with total page 396 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organocopper compounds are now an integral part of every modern synthesis laboratory, allowing important stages of synthesis to be carried out in an elegant fashion. Yet a certain amount of experience is needed if they are to be used effectively. Non-experts in the field often have difficulty in choosing the most suitable reagent for a particular substrate and the prerequisites for the reaction.This manual, edited by Norbert Krause, answers such questions, since it contains all the useful tips and tricks on organocopper compounds - information gained from personal experience by the international team of authors. This allows those working in laboratories in both academia and industry to determine the optimal reagent for their needs using the substrates available for reaction and the desired products. The result is a more effective use of these synthesis tools in everyday laboratory practice.
Download or read book Copper Catalyzed Multi Component Reactions written by Yusuke Ohta and published by Springer. This book was released on 2013-02-25 with total page 104 pages. Available in PDF, EPUB and Kindle. Book excerpt: A copper-catalyzed direct synthesis of 2-(aminomethyl)indoles by catalytic domino reaction including multi-component coupling was developed, and is the first example of a three-component indole formation without producing salts as a byproduct. Based on this reaction, a copper-catalyzed synthesis of 3-(aminomethyl)isoquinoline was accomplished which represents an unprecedented isoquinoline synthesis through a four-component coupling reaction. Following these results, extensive application studies using one-pot palladium-, acid-, or base-promoted cyclization revealed that indole- or isoquinoline-fused polycyclic compounds can be readily synthesized through multi-component reactions. As the concept of Green Chemistry becomes ever more important, these findings may provide efficient and atom-economical approaches to the diversity-oriented synthesis of bioactive compounds containing a complex structure. This could lead to development of promising drug leads with structural complexity. The work of this thesis will go on to inspire the synthetic research of many readers.
Download or read book Copper Catalyzed Multi Component Reactions written by Yusuke Ohta and published by Springer. This book was released on 2011-03-30 with total page 120 pages. Available in PDF, EPUB and Kindle. Book excerpt: As the concept of Green Chemistry becomes ever more important, the findings presented in this book may provide efficient and atom-economical approaches to the diversity-oriented synthesis of bioactive compounds containing a complex structure.
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 Computational Advances of Rh Catalyzed C H Functionalization written by Yu Lan and published by Springer Nature. This book was released on 2021-02-26 with total page 132 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book offers a comprehensive overview of recent theoretical studies on rhodium-catalyzed C-H functionalization, a topic that has attracted considerable attention over the years. It includes a brief experimental history, elementary reactions, and theoretical perspectives and describes in detail recent advanced computational studies on different types of Rh-catalyzed C-H functionalization, the underlying mechanisms, and the origin of regioselectivity in a series of such reactions. Providing examples shows readers how to use theoretical tools to solve problems related to mechanisms of organometallic reactions. As such, the book is an interesting and useful resource for a wide readership in various fields involving synthetic organic, organometallic, and catalysis reactions.
