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New Synthetic Applications Of Rhodium Catalyzed Carbon Carbon And Carbon Heteroatom Bond Forming Reactions
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Book Synopsis New Synthetic Applications of Rhodium-catalyzed Carbon-carbon and Carbon-heteroatom Bond Forming Reactions by : Gavin Chit Tsui
Download or read book New Synthetic Applications of Rhodium-catalyzed Carbon-carbon and Carbon-heteroatom Bond Forming Reactions written by Gavin Chit Tsui and published by . This book was released on 2013 with total page 348 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis New Synthetic Applications of Rhodium-catalyzed Carbon-carbon and Carbon-heteroatom Bond Forming Reactions by : Gavin Chit Tsui
Download or read book New Synthetic Applications of Rhodium-catalyzed Carbon-carbon and Carbon-heteroatom Bond Forming Reactions written by Gavin Chit Tsui and published by . This book was released on 2013 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author :Keith Fagnou Publisher :National Library of Canada = Bibliothèque nationale du Canada ISBN 13 :9780612745919 Total Pages :1052 pages Book Rating :4.7/5 (459 download)
Book Synopsis New Rhodium-catalyzed Carbon-carbon and Carbon-heteroatom Bond Forming Reactions for Organic Synthesis [microform] by : Keith Fagnou
Download or read book New Rhodium-catalyzed Carbon-carbon and Carbon-heteroatom Bond Forming Reactions for Organic Synthesis [microform] written by Keith Fagnou and published by National Library of Canada = Bibliothèque nationale du Canada. This book was released on 2002 with total page 1052 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Catalyzed Carbon-Heteroatom Bond Formation by : Andrei K. Yudin
Download or read book Catalyzed Carbon-Heteroatom Bond Formation written by Andrei K. Yudin and published by John Wiley & Sons. This book was released on 2010-12-01 with total page 541 pages. Available in PDF, EPUB and Kindle. Book excerpt: Written by an experienced editor widely acclaimed within the scientific community, this book covers everything fromo9xygen to nitrogen functionalities. From the contents: Palladium-Catalyzed Syntheses of Five-Member Saturated Heterocyclic and of Aromatic Heterodynes Palladium-Catalysis for Oxidative 1, 2-Difunctionalization of Alkenes Rhodium-Catalyzed Amination of C-H-Bonds Carbon-Heteroatom Bond Formation by RH(I)-Catalyzed Ring-Opening Reactions Transition Metal-Catalyzed Synthesis of Lactones and of Monocyclic and Fused Five-Membered Aromatic heterocycles the Formation of Carbon-Sulfur and Carbon-Selenium bonds by Substitution and Addition reactions catalyzed by Transition Metal Complexes New Reactions of Copper Acetylides Gold Catalyzed Addition of Nitrogen, Sulfur and Oxygen Nucleophiles to C-C Multiple Bonds. The result is an indispensable source of information for the Strategic Planning of the Synthetic routes for organic, catalytic and medicinal chemists, as well as chemists in industry.
Book Synopsis Modern Rhodium-Catalyzed Organic Reactions by : P. Andrew Evans
Download or read book Modern Rhodium-Catalyzed Organic Reactions written by P. Andrew Evans and published by John Wiley & Sons. This book was released on 2006-03-06 with total page 496 pages. Available in PDF, EPUB and Kindle. Book excerpt: Rhodium has proven to be an extremely useful metal due to its ability to catalyze an array of synthetic transformations, with quite often-unique selectivity. Hydrogenation, C-H activation, allylic substitution, and numerous other reactions are catalyzed by this metal, which presumably accounts for the dramatic increase in the number of articles that have recently emerged on the topic. P. Andrew Evans, the editor of this much-needed book, has assembled an internationally renowned team to present the first comprehensive coverage of this important area. The book features contributions from leaders in the field of rhodium-catalyzed reactions, and thereby provides a detailed account of the most current developments, including: Rhodium-Catalyzed Asymmetric Hydrogenation (Zhang) Rhodium-Catalyzed Hydroborations and Related Reactions (Brown) Rhodium-Catalyzed Asymmetric Addition of Organometallic Reagents to Electron Deficient Olefins (Hayashi) Recent Advances in Rhodium(I)-Catalyzed Asymmetric Olefin Isomerization and Hydroacylation Reactions (Fu) Stereoselective Rhodium(I)-Catalyzed Hydroformylation and Silylformylation Reactions and Their Application to Organic Synthesis (Leighton) Carbon-Carbon Bond-Forming Reactions Starting from Rh-H or Rh-Si Species (Matsuda) Rhodium(I)-Catalyzed Cycloisomerization and Cyclotrimerization Reactions (Ojima) The Rhodium(I)-Catalyzed Alder-ene Reaction (Brummond) Rhodium-Catalyzed Nucleophilic Ring Cleaving Reactions of Allylic Ethers and Amines (Fagnou) Rhodium(I)-Catalyzed Allylic Substitution Reactions and their Applications to Target Directed Synthesis (Evans) Rhodium(I)-Catalyzed [2+2+1] and [4+1] Carbocyclization Reactions (Jeong) Rhodium(I)-Catalyzed [4+2] and [4+2+2] Carbocyclizations (Robinson) Rhodium(I)-Catalyzed [5+2], [6+2], and [5+2+1] Cycloadditions: New Reactions for Organic Synthesis (Wender) Rhodium(II)-Stabilized Carbenoids Containing both Donor and Acceptor Substituents (Davies) Chiral Dirhodium(II)Carboxamidates for Asymmetric Cyclopropanation and Carbon-Hydrogen Insertion Reactions (Doyle) Cyclopentane Construction by Rhodium(II)-Mediated Intramolecular C-H Insertion (Taber) Rhodium(II)-Catalyzed Oxidative Amination (DuBois) Rearrangement Processes of Oxonium and Ammonium Ylides Formed by Rhodium(II)-Catalyzed Carbene-Transfer (West) Rhodium(II)-Catalyzed 1,3-Dipolar Cycloaddition Reactions (Austin) "Modern Rhodium-Catalyzed Organic Reactions" is an essential reference text for researchers at all levels in the general area of organic chemistry. This book provides an invaluable overview of the most significant developments in this important area of research, and will no doubt be an essential text for researchers at academic institutions and professionals at pharmaceutical/agrochemical companies.
Book Synopsis Rhodium-Catalyzed C-C Bond Formation Via Heteroatom-Directed C-H Bond Activation by :
Download or read book Rhodium-Catalyzed C-C Bond Formation Via Heteroatom-Directed C-H Bond Activation written by and published by . This book was released on 2010 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Once considered the 'holy grail' of organometallic chemistry, synthetically useful reactions employing C-H bond activation have increasingly been developed and applied to natural product and drug synthesis over the past decade. The ubiquity and relative low cost of hydrocarbons makes C-H bond functionalization an attractive alternative to classical C-C bond forming reactions such as cross-coupling, which require organohalides and organometallic reagents. In addition to providing an atom economical alternative to standard cross - coupling strategies, C-H bond functionalization also reduces the production of toxic by-products, thereby contributing to the growing field of reactions with decreased environmental impact. In the area of C-C bond forming reactions that proceed via a C-H activation mechanism, rhodium catalysts stand out for their functional group tolerance and wide range of synthetic utility. Over the course of the last decade, many Rh-catalyzed methods for heteroatom-directed C-H bond functionalization have been reported and will be the focus of this review. Material appearing in the literature prior to 2001 has been reviewed previously and will only be introduced as background when necessary. The synthesis of complex molecules from relatively simple precursors has long been a goal for many organic chemists. The ability to selectively functionalize a molecule with minimal pre-activation can streamline syntheses and expand the opportunities to explore the utility of complex molecules in areas ranging from the pharmaceutical industry to materials science. Indeed, the issue of selectivity is paramount in the development of all C-H bond functionalization methods. Several groups have developed elegant approaches towards achieving selectivity in molecules that possess many sterically and electronically similar C-H bonds. Many of these approaches are discussed in detail in the accompanying articles in this special issue of Chemical Reviews. One approach that has seen widespread success involves the use of a proximal heteroatom that serves as a directing group for the selective functionalization of a specific C-H bond. In a survey of examples of heteroatom-directed Rh catalysis, two mechanistically distinct reaction pathways are revealed. In one case, the heteroatom acts as a chelator to bind the Rh catalyst, facilitating reactivity at a proximal site. In this case, the formation of a five-membered metallacycle provides a favorable driving force in inducing reactivity at the desired location. In the other case, the heteroatom initially coordinates the Rh catalyst and then acts to stabilize the formation of a metal-carbon bond at a proximal site. A true test of the utility of a synthetic method is in its application to the synthesis of natural products or complex molecules. Several groups have demonstrated the applicability of C-H bond functionalization reactions towards complex molecule synthesis. Target-oriented synthesis provides a platform to test the effectiveness of a method in unique chemical and steric environments. In this respect, Rh-catalyzed methods for C-H bond functionalization stand out, with several syntheses being described in the literature that utilize C-H bond functionalization in a key step. These syntheses are highlighted following the discussion of the method they employ.
Book Synopsis Rhodium Catalysis in Organic Synthesis by : Ken Tanaka
Download or read book Rhodium Catalysis in Organic Synthesis written by Ken Tanaka and published by John Wiley & Sons. This book was released on 2019-05-06 with total page 684 pages. Available in PDF, EPUB and Kindle. Book excerpt: An essential reference to the highly effective reactions applied to modern organic synthesis Rhodium complexes are one of the most important transition metals for organic synthesis due to their ability to catalyze a variety of useful transformations. Rhodium Catalysis in Organic Synthesis explores the most recent progress and new developments in the field of catalytic cyclization reactions using rhodium(I) complexes and catalytic carbon-hydrogen bond activation reactions using rhodium(II) and rhodium(III) complexes. Edited by a noted expert in the field with contributions from a panel of leading international scientists, Rhodium Catalysis in Organic Synthesis presents the essential information in one comprehensive volume. Designed to be an accessible resource, the book is arranged by different reaction types. All the chapters provide insight into each transformation and include information on the history, selectivity, scope, mechanism, and application. In addition, the chapters offer a summary and outlook of each transformation. This important resource: -Offers a comprehensive review of how rhodium complexes catalyze a variety of highly useful reactions for organic synthesis (e.g. coupling reactions, CH-bond functionalization, hydroformylation, cyclization reactions and others) -Includes information on the most recent developments that contain a range of new, efficient, elegant, reliable and useful reactions -Presents a volume edited by one of the international leading scientists working in the field today -Contains the information that can be applied by researchers in academia and also professionals in pharmaceutical, agrochemical and fine chemical companies Written for academics and synthetic chemists working with organometallics, Rhodium Catalysis in Organic Synthesis contains the most recent information available on the developments and applications in the field of catalytic cyclization reactions using rhodium complexes.
Author :Piet W.N.M. van Leeuwen Publisher :Springer Science & Business Media ISBN 13 :0306469472 Total Pages :291 pages Book Rating :4.3/5 (64 download)
Book Synopsis Rhodium Catalyzed Hydroformylation by : Piet W.N.M. van Leeuwen
Download or read book Rhodium Catalyzed Hydroformylation written by Piet W.N.M. van Leeuwen and published by Springer Science & Business Media. This book was released on 2006-04-11 with total page 291 pages. Available in PDF, EPUB and Kindle. Book excerpt: In the last decade there have been numerous advances in the area of rhodium-catalyzed hydroformylation, such as highly selective catalysts of industrial importance, new insights into mechanisms of the reaction, very selective asymmetric catalysts, in situ characterization and application to organic synthesis. The views on hydroformylation which still prevail in the current textbooks have become obsolete in several respects. Therefore, it was felt timely to collect these advances in a book. The book contains a series of chapters discussing several rhodium systems arranged according to ligand type, including asymmetric ligands, a chapter on applications in organic chemistry, a chapter on modern processes and separations, and a chapter on catalyst preparation and laboratory techniques. This book concentrates on highlights, rather than a concise review mentioning all articles in just one line. The book aims at an audience of advanced students, experts in the field, and scientists from related fields. The didactic approach also makes it useful as a guide for an advanced course.
Book Synopsis Transition Metal-catalyzed Carbon-carbon/carbon-heteroatom Bond Formation Reactions Utilizing Strained Ring Systems by : Nai-Wen Tseng
Download or read book Transition Metal-catalyzed Carbon-carbon/carbon-heteroatom Bond Formation Reactions Utilizing Strained Ring Systems written by Nai-Wen Tseng and published by . This book was released on 2009 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: This thesis focuses on the development of carbon-carbon/carbon-heteroatom bond forming reactions using strained ring systems under transition metal catalysis. The first chapter describes the use of bifunctional organoboron reagents with a rhodium catalyst to synthesize carbocycles through a cascade sequence. The reaction of norbornene derivatives gives vinylcyclopropane and cyclopentene products in moderate to good yield. The mechanistic proposal and insights into the reaction mechanism are presented. Preliminary results from studies toward an enantioselective sequential addition/cyclization process are described. The methodology is subsequently applied in the synthesis of a variety of polycyclic heteroaromatics using bifunctional heteroaryl boronate esters. The second chapter describes studies toward the formation of carbon-heteroatom bonds using cyclopropane derivatives. Under a recently developed Pd(OAc) 2/PhI(OAc)2 catalytic system, methylenecyclopropanes are isomerized to substituted pyridines via a sequential fragmentation/cyclization process. Under same reaction conditions, allylic acetate products are obtained from the isomerization of cyclopropanes through a similar process.
Book Synopsis Reversible Oxidative Addition in Palladium Catalysis by : Stephen Newman
Download or read book Reversible Oxidative Addition in Palladium Catalysis written by Stephen Newman and published by . This book was released on 2012 with total page 986 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Rhodium-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes and Palladium-Catalyzed Carbon-Halogen Bond Forming Reactions by : Christine Le
Download or read book Rhodium-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes and Palladium-Catalyzed Carbon-Halogen Bond Forming Reactions written by Christine Le and published by . This book was released on 2017 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Atom-economical addition reactions to unsaturated carbonâ carbon bonds represent a powerful class of transformations in organic chemistry, since a great deal of molecular complexity can be generated from simple starting materials. Highly regio- and stereoselective processes have been made possible through the use of transition metal catalysts, alongside specialized ancillary ligands and in combination with rational substrate design. One area of research in the Lautens group involves the transition metal catalyzed asymmetric ring opening (ARO) of strained alkenes, which provides access to enantioenriched carbocyclic frameworks. Although a variety of coupling partners have been applied in this transformation, the use of soft carbon nucleophiles remains limited in scope. The first chapter describes a rhodium(I)-catalyzed ARO of meso-oxabicyclic alkenes using silyl enol ethers and ketene acetals. In analogy to the Mukaiyama aldol reaction, a novel silyl migration occurs, enabling an in situ protection of the chiral alcohols obtained. Developing new reactivity from Heck-type carbopalladation processes represents another research interest in the Lautens group. Oxidative addition into a carbonâ halogen bond constitutes the first step of nearly all palladium(0)-catalyzed cross-couplings. Conversely, reductive elimination from palladium(II) to yield an organohalide product represents a rare and often thermodynamically unfavoured process. The next two chapters address challenges in the synthesis of vinyl halides using palladium(0) catalysis via the intramolecular carbohalogenation and chlorocarbamoylation of alkynes. During our investigations, we discovered that the steric bulk of both the substrate and the phosphine ligand play an important role in promoting the desired reactivity. Mechanistic insight has been gained through combined experimental and computational studies, which implicate a palladium-catalyzed stereoisomerization in both of these transformations. Under certain conditions, we demonstrate that highly stereoselective trans-additions to alkynes can be achieved, which illustrates that specific substrate/catalyst combinations can override the inherent cis-selectivity in carbometallations. In the fourth chapter, a formal palladium(II)-catalyzed alkyne chlorocarbamoylation reaction is presented, which provides access to medicinally relevant methylene oxindole scaffolds. In contrast to the analogous protocol using palladium(0) catalysts, the reaction is initiated by an alkyne chloropalladation step, followed by intramolecular cross-coupling with a carbamoyl chloride. Experimental and computational studies provide insight into the mechanism of this reaction.
Book Synopsis Cleavage of Carbon-Carbon Single Bonds by Transition Metals by : Masahiro Murakami
Download or read book Cleavage of Carbon-Carbon Single Bonds by Transition Metals written by Masahiro Murakami and published by John Wiley & Sons. This book was released on 2015-09-21 with total page 292 pages. Available in PDF, EPUB and Kindle. Book excerpt: Edited by leading experts and pioneers in the field, this is the first up-to-date book on this hot topic. The authors provide synthetic chemists with different methods to activate carbon-carbon sigma bonds in organic molecules promoted by transition metal complexes. They explain the basic principles and strategies for carbon-carbon bond cleavage and highlight recently developed synthetic protocols based on this methodology. In so doing, they cover cleavage of C-C bonds in strained molecules, reactions involving elimination of carbon dioxide and ketones, reactions via retroallylation, and cleavage of C-C bonds of ketones and nitriles. The result is an excellent information source for researchers in academia and industry working in the field of synthetic organic chemistry, while equally serving as supplementary reading for advanced courses in organometallic chemistry and catalysis.
Book Synopsis New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation by : Rui Shang
Download or read book New Carbon–Carbon Coupling Reactions Based on Decarboxylation and Iron-Catalyzed C–H Activation written by Rui Shang and published by Springer. This book was released on 2016-12-09 with total page 225 pages. Available in PDF, EPUB and Kindle. Book excerpt: This thesis presents the latest developments in new catalytic C–C bond formation methods using easily accessible carboxylate salts through catalytic decarboxylation with good atom economy, and employing the sustainable element iron as the catalyst to directly activate C–H bonds with high step efficiency. In this regard, it explores a mechanistic understanding of the newly discovered decarboxylative couplings and the catalytic reactivity of the iron catalyst with the help of density functional theory calculation. The thesis is divided into two parts, the first of which focuses on the development of a series of previously unexplored, inexpensive carboxylate salts as useful building blocks for the formation of various C–C bonds to access valuable chemicals. In turn, the second part is devoted to several new C–C bond formation methodologies using the most ubiquitous transition metal, iron, as a catalyst, and using the ubiquitous C–H bond as the coupling partner.
Book Synopsis Catalysis of Carbon-carbon and Carbon-heteroatom Bond-forming Reactions by : Catherine Suzanne Julienne Cazin
Download or read book Catalysis of Carbon-carbon and Carbon-heteroatom Bond-forming Reactions written by Catherine Suzanne Julienne Cazin and published by . This book was released on 2002 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis New Methods for Carbon-carbon Bond Formation and Application to Organic Synthesis by : Christopher James Dockendorff
Download or read book New Methods for Carbon-carbon Bond Formation and Application to Organic Synthesis written by Christopher James Dockendorff and published by . This book was released on 2006 with total page 748 pages. Available in PDF, EPUB and Kindle. Book excerpt: Tetralins with a desired 1,4-substitution pattern were synthesized via Diels-Alder reactions between arynes and acyclic dienes. We have shown this underutilized reaction to be useful for the stereospecific synthesis of 1,4-dihydronaphthalenes which are not readily accessible via other methods. Preliminary efforts to render this reaction asymmetric are presented; excellent diastereoselectivities were observed using Oppolzer's sultam as a chiral auxiliary on the diene. A short synthesis of racemic sertraline was also carried out using the aryne Diels-Alder reaction as the key step. We have reported the rhodium-catalyzed asymmetric ring-opening reaction of oxabicyclic alkenes with aryl- and alkenylboron nucleophiles. The reactions generally proceed with excellent yield and enantioselectivity under mild conditions, giving only one diastereomer (cis adducts). The Rh(I) catalyst system utilizes the ferrocenyl bisphosphine ligand PPF-P(t-Bu) 2. This ligand is also very efficient for the ring-opening reactions with heteroatom nucleophiles, which proceed via a different mechanism and give trans products. We have recently discovered that other Rh(I) catalysts can promote the highly enantio- and regioselective desymmetrization of meso-diols via allylic substitution reactions with organoborons. Some of the limitations of the rhodium-catalyzed ring-opening reactions were overcome by the development of Pd(II) catalyst systems. These catalysts give excellent yields (albeit currently with decreased enantioselectivities relative to the rhodium reactions) under very mild conditions (undistilled methanol, room temperature, open to the air). The Pd(II) systems also work very well with azabicyclic alkenes and with heteroaryl- and ortho -substituted arylboronic acids, which all were problematic with rhodium catalysts. They also show some promise with alkylboron species. Various metal-catalyzed ring-opening reactions have been utilized to make gram-scale tetralin scaffolds for drug discovery efforts. The scaffolds were subsequently functionalized to yield libraries of amides, amines, and ureas for screening against a variety of biological targets. Several opioid receptor antagonists were subsequently identified by our industrial collaborators.
Book Synopsis Transition Metal-catalyzed Carbon-carbon/Carbon-heteroatom Bond Formation Reactions Utilizing Strained Ring Systems by :
Download or read book Transition Metal-catalyzed Carbon-carbon/Carbon-heteroatom Bond Formation Reactions Utilizing Strained Ring Systems written by and published by . This book was released on 2002 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: PhD.
Book Synopsis Rhodium-catalyzed Asymmetric Carbon-Carbon Bond Formation Leading to the Development of Rhodium/Palladium Multi-metal Catalysis by : Lei Zhang
Download or read book Rhodium-catalyzed Asymmetric Carbon-Carbon Bond Formation Leading to the Development of Rhodium/Palladium Multi-metal Catalysis written by Lei Zhang and published by . This book was released on 2015 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: This thesis describes the development of rhodium-catalyzed asymmetric ring opening of strained alkenes and the subsequent use of rhodium and palladium catalysis in the development of domino reactions. The contents are divided into 4 chapters. Chapter 1 describes the rhodium-catalyzed asymmetric ring opening (ARO) of strained bicyclic alkenes using silyl enolates. The development of this method achieved a highly enantioselective addition of alkyl fragments onto bicyclic alkenes, affording broad scope, mild reaction conditions, and high functional group tolerance. The synthetic utility of the method was demonstrated through functionalization of the ARO products to a number of core scaffolds of natural products. Chapter 2 describes the development of a domino rhodium/palladium-catalyzed synthesis of dihydroquinolines. The use of two different ligands in the reaction led to a mechanistic investigation that revealed metal-ligand interactions that were crucial to the success of this domino reaction. The mechanistic insights facilitated reaction optimization, leading to an expansion of the reaction scope, including the synthesis of chromenes. Chapter 3 describes the importance of time resolution and ligand interference in the development of enantioselective domino rhodium/palladium catalysis employing chiral and achiral ligands. The development of this method provided access to chiral C4-substituted dihydroquinolinones in a direct manner, affording high yields and enantioselectivities. Current work on developing multicomponent enantioselective rhodium/palladium catalysis is also disclosed. Chapter 4 describes the development of multi-metal-catalyzed multicomponent reactions (MC)2R. The development of a highly compatible rhodium/palladium catalyst system allowed the incorporation of a third catalyst, copper, achieving a three-component one-pot reaction. Current work on the development of the use of other metal combinations to achieve (MC)2R is also disclosed.
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