Download or read book Advances in Late Metal Carbon Nitrogen Bond Formation for the Synthesis of Substituted Heterocycles written by Nicolas Rotta-Loria and published by . This book was released on 2017 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Late-metal catalyzed cross-couplings have emerged as efficient and selective methodologies for the formation of C-C and C-N bonds. The ability to synthesize complex heterocycles from cheap and abundant starting materials is an invaluable asset to the pharmaceutical industry, given that many pharmaceuticals contain at least one heterocyclic component. This reactivity can be achieved by tuning the steric and electronic properties of ancillary ligands to support metal catalysts in the reaction steps leading to the target substrate. The Stradiotto group has developed several state-of-the-art methodologies involving ligands for palladium catalysis, for both C-C and C-N bond-forming reactions. These methodologies can be amalgamated into a multicomponent reaction platform to synthesize more complex products from simple materials. Chapter 1 outlines this concept with the application of a Mor-DalPhos/Pd catalyst in the one-pot synthesis of indoles from acetone and simple amines involving C-C and C-N bond formation. The robust nature of this method can be extended to include benchtop reaction conditions in a one-step, one-pot synthesis of indoles, thus representing a useful synthetic protocol. While palladium provides a powerful tool for C-C and C-N bond formation, the general trend in catalysis has shifted away from the precious metals toward first row metals as economic alternatives. Nickel complexes have recently emerged as excellent catalysts for a number of amination reactions. The ability to utilize ammonia also represents a sought after reaction, due to the widespread availability and synthetic utility of amino-functionalized products. In this regard, Chapter 2 will focus on the development and application of both commercially available and strategically designed ligand classes for the monoarylation of ammonia with substituted heterocycles. Hydrazine represents an important synthon in synthetic chemistry. It is synthesized on multi-ton scale every year and represents an important building block in many industrial processes. Many synthetic challenges arise from using free hydrazine as reactant, which has led to lethargic growth of its application in the field of late-metal catalyzed C-N bond-formation. However, gold-catalyzed methodologies have been developed utilizing NHC ligands to allow for the hydrohydrazination of alkynes with parent hydrazine. Chapter 4 examines the development and application of a series of (PR3)AuCl complexes for use in such transformations, leading to the identification of the first effective phosphine-bound gold complex for use in the hydrohydrazination of alkynes at room temperature.
Download or read book Metals and Non metals written by Navjeet Kaur and published by CRC Press. This book was released on 2020-01-28 with total page 404 pages. Available in PDF, EPUB and Kindle. Book excerpt: Design of new processes that avoid the use of toxic reagents has been the focus of intense research of late. Catalysis by metals and non-metals offers diverse opportunities for the development of new organic reactions with promising range of selectivities—chemoselectivity, regioselectivity, diastereoselectivity, and enantioselectivity. Furthermore, these transformations frequently occur under mild conditions, tolerate a broad array of functional groups, and proceed with high stereoselectivity. The area of catalysis is sometimes referred to as a ‘foundational pillar’ of green chemistry. Catalytic reactions often reduce energy requirements and decrease separations because of increased selectivity; they are also capable of permitting the use of renewable feedstocks of less toxic reagents or minimizing the quantities of reagents needed. New catalytic organic synthesis methodologies have, thus, offered several possibilities for considerable improvement in the eco-compatibility of fine chemical production. Hence, these catalytic methodologies have emerged as powerful tools for the efficient and chemoselective synthesis of heterocyclic molecules. Key Features: Presents the synthesis of different five-membered heterocycles. Contains the most up-to-date information in this fast-moving field. Covers novel catalytic approaches used in the study and application of catalysts in synthetic organic reactions. Presents new methodologies for the synthesis of heterocycles.
Download or read book Heterocycles via Cross Dehydrogenative Coupling written by Ananya Srivastava and published by Springer Nature. This book was released on 2019-08-23 with total page 494 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book discusses the developments in the synthesis and functionalization of different heterocycles based on the formation of carbon-carbon (C-C) and carbon-heteroatom (C-X) bonds using cross-dehydrogenative coupling (CDC). Consisting of 13 chapters, the book systematically describes the advances in the synthesis and functionalization of nitrogen, oxygen, and sulfur-containing heterocycles. It also discusses the various mechanistic pathways to help readers gain an in-depth understanding of the CDC reactions of heterocycles. Lastly, in order to promote green chemistry, it addresses a range of metal-free CDC reactions of heterocycles – an area that has attracted significant attention in both academic and industrial research.
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.
Download or read book Heterocycles from Transition Metal Catalysis written by András Kotschy and published by Springer Science & Business Media. This book was released on 2005-09-30 with total page 224 pages. Available in PDF, EPUB and Kindle. Book excerpt: "Heterocycles from Transition Metal Catalysis: Formation and Functionalization" provides a concise summary of the prominent role of late transition metal (palladium, nickel, copper) catalysed processes in the synthesis and functionalization of heterocyclic systems. It gives an introduction to catalytic transformations, an overview of the most important reaction types, and presents synthetically useful catalytic processes classified by the target system and the type of transformation. The book provides a representative selection of transition metal catalysed reactions transformations that are relevant in heterocyclic chemistry. In this way, the authors present a useful resource for members of the academic community looking for a textbook as well as industrial chemists in search of a reference book. This book will be an invaluable resource for synthetic chemists, medicinal chemists, and those more generally interested in applied catalysis.
Download or read book Transition Metal catalyzed Preparation and Functionalization of Nitrogen containing Heterocycles written by Malcolm P. Huestis and published by . This book was released on 2009 with total page 148 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Synthesis of Nitrogenous Heterocycles Via Group 3 Metal catalyzed Hydroamination and Zinc II Mediated Metalloamination written by Adrian Robert Smith and published by . This book was released on 2015 with total page 149 pages. Available in PDF, EPUB and Kindle. Book excerpt: Pyrrolidines and piperidines respresent a motif found in a wide array of bioactive compounds. Hydroamination, or the insertion of a carbon-nitrogen bond into a site of unsaturation, represents an atom economical method for accessing substituted pyrrolidines and piperidines. Synthesis of nitrogenous heterocycles through group 3 metal hydroamination and zinc(II) metalloamination has been achieved. The hydroamination of aminoalkenes has been thoroughly screened and has shown good tolerance for ethereal solvents, and solvent choice can result in improved rate and diastereoselectivity. The hydroamination of secondary amines with electron rich heteroatoms has also been realized utilizing a new group 3 metal trisamide developed in these labs. Additionally, zinc(II) metalloamination has been performed on N, N-dimethylhydrazinoalkenes and successfully resulted in the synchronous formation of a nitrogen-carbon bond to form a ring as well as carbon-zinc bond formation at the adjacent carbon. This carbon-zinc bond has been intercepted by different carbon electrophiles to synchronously form a nitrogen-carbon bond and carbon-carbon bond in situ. Ligand studies for these transformations suggest 1,1,1-trifluoroacetylenamines as well as acetoacetamides are promising motifs for future ligand scaffolds due to their ease of synthesis, low cost, and good reactivity with a range of N, N-dimethylhydrazinoalkene substrates.
Download or read book Synthesis of Heterocycles Using Group 4 Metal Catalyzed C N Bond Formation written by Supriyo Majumder and published by . This book was released on 2009 with total page 502 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Novel Approaches to Synthesis of Nitrogen Containing Heterocycles microform written by Ghotas Evindar and published by National Library of Canada = Bibliothèque nationale du Canada. This book was released on 2004 with total page 1174 pages. Available in PDF, EPUB and Kindle. Book excerpt: In Chapter one, a modified approach for mercury promoted synthesis of mono-, di- and tri-substituted 5-aminotetrazoles, and 5-oxo-tetrazoles is reported. This mild protocol is applied to one pot synthesis of a number of amino acid tert-butyl ester- and peptide tert-butyl ester-tetrazole conjugates. It allows for incorporation of a tetrazole moiety into peptide structures. Finally, a solid phase synthetic protocol to incorporate tetrazole heterocycles at the N-terminus of a peptide, using HgCl2, DIC, or Mukaiyama's reagents was achieved. Chapter three describes the synthesis of 2-aminobenzimidazoles via intramolecular C-N bond formation between an aryl halide and a guanidine moiety using either copper or palladium catalysis. Inexpensive copper salts, such as CuI, are generally superior to the use of palladium catalysts. Regioselective cyclizations can also be achieved in high yield under CuI/1,10-phenanthroline catalyzed conditions, whereas palladium catalysis results in the formation of regioisomeric products. Copper- and palladium-catalyzed intramolecular C-S bond formation by cross-coupling between an aryl halide and thiourea functionality is also demonstrated for the synthesis of 2-aminobenzothiazoles. The copper-catalyzed reaction further expands the recent studies exploring the utility of copper salts as replacements for palladium in carbon-heteroatom bond forming reactions. This methodology is applied to the synthesis of the histamine H1-receptor antagonist astemizole (Hismanal) and its highly active metabolite norastemizole. This work is the first serious study of metal catalyzed arylation of guanidines, and is one of a handful of examples of copper catalyzed cyclizations involving C-N bond formation. Chapter two describes a modified Edman degradation procedure to provide an effective means of introducing a heterocycle at the N-terminus of an amino acid amide or peptide. Reaction of a peptide with an isothiocyanate, followed by dehydrothiolative trapping of the intermediate thiourea by intramolecular cyclization of the weakly nucleophilic adjacent amide nitrogen, generates an iminohydantoin. Solution-phase parallel synthesis of iminohydantoins and polymer-supported synthesis of dipeptide and tripeptide derived iminohydantoins were also achieved. Chapter four describes the formation of various benzoxazoles and a handful of benzthiazoles via intramolecular C-O cross-coupling between an aryl halide and an amide oxygen/sulfur using a catalytic amount of copper. Investigation of various ligands revealed 1,10-phenanthroline to be a superior ligand in benzoxazole formation. This protocol allowed for aryl, alky, vinyl, and hetero-aromatic substitutions at position 2-oxazole. A number of substitutions on the phenyl ring of benzoxazole were also well tolerated. An intermolecular approach has also been investigated. The developed intramolecular protocol is applied to total synthesis of antitumor agent UK-1 46 and its analog Me-UK-1 47. Also, a new protocol for the formation of substituted aminothiatriazoles from thiocarbamoylimidazolium salts is outlined. Thiocarbamoylimidazolium salts are synthesized from the corresponding amines by treatment with thiocarbonyldiimidazole (TCDI) followed by methylation with iodomethane. Thiocarbamoylimidazolium salts are shown to act as thiocarbamoyl cation equivalents. Substitution of the salts by azide anion followed by electrocyclization affords substituted aminothiatriazoles in good to excellent yields.
Download or read book Catalytic Methods for Carbon carbon and Carbon nitrogen Bond Formation written by Stephen David Ramgren and published by . This book was released on 2014 with total page 511 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation describes the study of metal-catalyzed cross-coupling reactions to construct carbon-carbon and carbon-heteroatom bonds. The key feature of much of this work is the use of inexpensive Ni and Fe catalysts to enable the coupling of unconventional electrophilic substrates, specifically aryl O-sulfamates and O-carbamates. The ability to use O-sulfamates and O-carbamates in catalytic processes is notable, as these substrates are readily derived from phenols and can be used for directed arene functionalization. Chapter one provides a summary of the efforts towards using alcohol-based solvents for the Suzuki-Miyaura cross-coupling reaction. Emphasis is placed on the cross-coupling of heterocycles, which are commonly encountered in natural product synthesis and in the pharmaceutical sector. Chapters two, three, and four describe carbon-nitrogen bond forming reactions. Chapter two pertains to the nickel-catalyzed amination of sulfamates, which culminated in the synthesis of the antibacterial drug, linezolid. Chapter three covers the amination of aryl O-carbamates and their use in sequential functionalization/site-selective cross-couplings. Chapter four describes a more user-friendly variant of the amination reaction, which relies on a bench-stable Ni(II) precatalyst, rather than a more commonly used Ni(0) precatalyst. Chapters five, six, and seven focus on carbon-carbon bond formation via Fe-, Ni- and Pd-mediated processes. Chapter five pertains to iron-catalyzed couplings of sulfamates and carbamates to generate sp2-sp3 carbon-carbon bonds. This method can be used to assemble sterically-congested frameworks. Chapter six describes the nickel-catalyzed Suzuki-Miyaura reactions of halides and phenol derivatives in `green' solvents, which was applied to the preparative scale assembly of bis(heterocycles) using low nickel catalyst loadings. Chapter seven pertains to the acetylation of arenes using palladium catalysis, which provides a simple and efficient means for the construction of a variety of aryl methyl ketones.
Download or read book Au Catalyzed Synthesis and Functionalization of Heterocycles written by Marco Bandini and published by Springer. This book was released on 2016-07-01 with total page 294 pages. Available in PDF, EPUB and Kindle. Book excerpt: The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field. All chapters from Topics in Heterocyclic Chemistry are published Online First with an individual DOI. In references, Topics in Heterocyclic Chemistry is abbreviated as Top Heterocycl Chem and cited as a journal
Download or read book Organic Chemistry of Explosives written by Jai Prakash Agrawal and published by John Wiley & Sons. This book was released on 2007-01-11 with total page 414 pages. Available in PDF, EPUB and Kindle. Book excerpt: Organic Chemistry of Explosives is the first text to bring together the essential methods and routes used for the synthesis of organic explosives in a single volume. Assuming no prior knowledge, the book discusses everything from the simplest mixed acid nitration of toluene, to the complex synthesis of highly energetic caged nitro compounds. Reviews laboratory and industrial methods, which can be used to introduce aliphatic C-nitro, aromatic C-nitro, N-nitro, and nitrate ester functionality into organic compounds Discusses the advantages and disadvantages of each synthetic method or route, with scope, limitations, substrate compatibility and other important considerations Features numerous examples in the form of text, reaction diagrams, and tables.
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 431 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.
Download or read book Metal Catalyzed Cross Coupling Reactions and More written by Armin de Meijere and published by John Wiley & Sons. This book was released on 2013-12-04 with total page 1640 pages. Available in PDF, EPUB and Kindle. Book excerpt: This three volume book is the follow-up handbook to the bestselling volume "Metal-Catalyzed Cross-Coupling Reactions", the definitive reference in the field. In line with the enormous developments in this area, this is not a new edition, but rather a new book in three volumes with over 50% more content. This new content includes C-H activation, shifting the focus away from typical cross-coupling reactions, while those topics and chapters found in de Meijere/Diederich's book have been updated and expanded. With its highly experienced editor team and the list of authors reading like an international Who's-Who in the field, this work will be of great interest to every synthetic chemist working in academia and industry.
Download or read book Advances in Cross Coupling Reactions written by José Pérez Sestelo and published by MDPI. This book was released on 2020-12-03 with total page 234 pages. Available in PDF, EPUB and Kindle. Book excerpt: In this Special Issue, recent advances in cross-coupling reactions are presented in the form of original research articles, reviews, and short communications. These contributions cover different topics in this area, including novel coupling reactions, reaction conditions, synthetic alternatives, metal ligands, and applications for new pharmaceutical compounds and organic materials. In particular, the reviews deal with methodologies such as the synthesis of diarylketones through palladium catalysis and the most relevant examples of Suzuki–Miyaura and Buchwald–Hartwig coupling reactions in the synthesis of bioactive compounds. The synthetic utility of cross-coupling reactions for the synthesis of medium-size rings and the utility of Stille and Suzuki coupling reactions for the synthesis of new molecular machines based on sterically hindered anthracenyl trypticenyl units are also summarized. The original research articles present the synthesis of 2-alkynylpyrrols by inverse Sonogashira coupling and the synthesis of indoles under oxidative dearomative cross-dehydrogenative conditions. The efficient combination of iridium-catalyzed C–H borylation of aryl halides with the Sonogashira coupling and a sequential iridium-catalyzed borylation of NH-free pyrroles followed by a Suzuki–Miyaura reaction are included. The synthesis of aryl propionic acids, a common structural motif in medicinal chemistry, and the synthesis of new organic dyes are also covered.
Download or read book Palladium Assisted Synthesis of Heterocycles written by Navjeet Kaur and published by CRC Press. This book was released on 2019-05-01 with total page 482 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book is a compilation of the recent applications of palladium catalysts in organic synthesis. The book demonstrates that it is a highly dynamic research field. This methodology has emerged as a powerful tool for the efficient and chemoselective synthesis of heterocyclic molecules. In the past few years, several strategies have been pointed out to pursue more efficient, sustainable, and environment friendly chemical processes. Among those strategies, catalysis and the design of new processes that avoid the use of toxic reagents have been the focus of intense research.
Download or read book Bio Based Solvents written by François Jérôme and published by John Wiley & Sons. This book was released on 2017-06-29 with total page 183 pages. Available in PDF, EPUB and Kindle. Book excerpt: A multidisciplinary overview of bio-derived solvent applications, life cycle analysis, and strategies required for industrial commercialization This book provides the first and only comprehensive review of the state-of-the-science in bio-derived solvents. Drawing on their own pioneering work in the field, as well as an exhaustive survey of the world literature on the subject, the authors cover all the bases—from bio-derived solvent applications to life cycle analysis to strategies for industrial commercialization—for researchers and professional chemists working across a range of industries. In the increasingly critical area of sustainable chemistry, the search for new and better green solvents has become a top priority. Thanks to their renewability, biodegradability and low toxicity, as well as their potential to promote advantageous organic reactions, green solvents offer the promise of significantly reducing the pernicious effects of chemical processes on human health and the environment. Following an overview of the current solvents markets and the challenges and opportunities presented by bio-derived solvents, a series of dedicated chapters cover all significant classes of solvent arranged by origin and/or chemical structure. Throughout, real-world examples are used to help demonstrate the various advantages, drawbacks, and limitations of each class of solvent. Topics covered include: The commercial potential of various renewably sourced solvents, such as glycerol The various advantages and disadvantages of bio-derived versus petroleum-based solvents Renewably-sourced and waste-derived solvents in the design of eco-efficient processes Life cycle assessment and predictive methods for bio-based solvents Industrial and commercial viability of bio-based solvents now and in the years ahead Potential and limitations of methodologies involving bio-derived solvents New developments and emerging trends in the field and the shape of things to come Considering the vast potential for new and better products suggested by recent developments in this exciting field, Bio-Based Solvents will be a welcome resource among students and researchers in catalysis, organic synthesis, electrochemistry, and pharmaceuticals, as well as industrial chemists involved in manufacturing processes and formulation, and policy makers.
