Read Books Online and Download eBooks, EPub, PDF, Mobi, Kindle, Text Full Free.
Development And Application Of Palladium Catalyzed Carbon Nitrogen Bond Forming Reactions
Download Development And Application Of Palladium Catalyzed Carbon Nitrogen Bond Forming Reactions full books in PDF, epub, and Kindle. Read online Development And Application Of Palladium Catalyzed Carbon Nitrogen Bond Forming Reactions ebook anywhere anytime directly on your device. Fast Download speed and no annoying ads. We cannot guarantee that every ebooks is available!
Book Synopsis Development and Application of Palladium-catalyzed Carbon-nitrogen Bond Forming Reactions by : Seble-Hiwot Teshome Wagaw
Download or read book Development and Application of Palladium-catalyzed Carbon-nitrogen Bond Forming Reactions written by Seble-Hiwot Teshome Wagaw and published by . This book was released on 1999 with total page 280 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Developments and Applications of Methods for Palladium- and Copper-catalyzed Carbon-nitrogen Bond Formation by : Jeffrey Chih-Yeh Yang
Download or read book Developments and Applications of Methods for Palladium- and Copper-catalyzed Carbon-nitrogen Bond Formation written by Jeffrey Chih-Yeh Yang and published by . This book was released on 2018 with total page 467 pages. Available in PDF, EPUB and Kindle. Book excerpt: The studies presented in this dissertation are aimed at the development and application of methodologies that enable carbon-nitrogen (C-N) bond formation catalyzed by late transition metals such as palladium and copper. The first part of this thesis focuses on the use of palladium catalysis for the construction of a carbon(sp2)-nitrogen bond in the context of a biphasic continuous-flow system (Chapter 1). The second part of this thesis describes the recent developments of copper-hydride (CuH) catalyzed asymmetric hydroamination for the formation of a-chiral carbon(sp3)-nitrogen bonds from olefins. This work includes the application of CuH catalysis to the synthesis of chiral N-alkyl aziridines (Chapter 2), and the discovery and development of novel electrophilic amines to enable CuH-catalyzed asymmetric hydroamination to directly access primary amines (Chapter 3). Part I. Chapter 1. Use of a "Catalytic" Cosolvent, N,N-Dimethyl Octanamide, Allows the Flow Synthesis of Imatinib with no Solvent Switch A general, efficient method for C-N cross-coupling has been developed using N,N-dimethyloctanamide as a cosolvent for biphasic continuous-flow applications. In addition to utilizing a proper co-solvent, the described method harnesses the superior mixing abilities of a stainless-steel powder packed tube reactor to efficiently couple a wide range of aryl/heteroaryl halides and aryl/heteroaryl/alkyl amines in a short period of time (
Book Synopsis Amination and Formation of sp2 C-N Bonds by : Marc Taillefer
Download or read book Amination and Formation of sp2 C-N Bonds written by Marc Taillefer and published by Springer. This book was released on 2013-12-12 with total page 233 pages. Available in PDF, EPUB and Kindle. Book excerpt: Palladium-Catalyzed sp2C–N Bond Forming Reactions: Recent Developments and Applications. Metal-catalyzed C(sp2)-N bond formation.- Recent Developments in Recyclable Copper Catalyst Systems for C−N Bond Forming Cross-Coupling Reactions Using Aryl Halides and Arylboronic Acids. Assembly of N-containing heterocycles via Pd and Cu-catalyzed C-N bond formation reactions. Copper-Catalyzed C(aryl)-N Bond Formation.
Book Synopsis Palladium Catalyzed Carbon-nitrogen Bond Formation by : Alejandra Domínguez Huerta
Download or read book Palladium Catalyzed Carbon-nitrogen Bond Formation written by Alejandra Domínguez Huerta and published by . This book was released on 2021 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: "This thesis describes the design and development of reductive amination methodologies of unactivated carbon-oxygen bonds using palladium on charcoal as a heterogeneous catalyst. The underlying premise is the transformation of starting materials that can be obtained from bio-renewable resources into commodity chemicals. Specifically, 2-cyclohexen-1-one and phenol were used as lignin building-block surrogates for C-N bond formation. The first chapter places the work developed in this thesis both in a global and a scientific context. Its objective is to provide an overview of our societal needs while describing the latest scientific developments related to this thesis topic. Thus, it begins by exploring the United Nation's Sustainable Goals, followed by an overview of petroleum and lignin chemistry, and finishes with a review on amino acid N-modification. In chapter two, the development of a novel methodology for the N-arylation of [alpha]-amino acids using 2-cyclohexen-1-one is described. Palladium on carbon was chosen as the catalyst, and several reaction conditions were explored to obtain optimal yields. This methodology's attractiveness lies in the absence of an aryl halide or protecting group on the 2-cyclohexen-1-one for the N-arylation to proceed. The reaction requires substoichiometric amounts of base and oxygen as the terminal oxidant. Aliphatic amino acids were ideal substrates for the reaction, and cyclohexanone provided the N-biarylated amino acids in good yields (up to 74%). Chapter three describes efforts to improve the harsh conditions required for the N-arylation of [alpha]-amino acids, resulting in the development of a novel methodology for their N-cyclohexylation in water, at room temperature, using phenol as a coupling partner. The reaction successfully achieves N-cyclohexylation for 17 out of the 20 naturally occurring amino acids without racemization with up to quantitative yields. Furthermore, small peptides were also successful substrates for the reaction. The fourth chapter explores the possibility of applying the latter methodology for the formation of one- and two-component peptide staples using tyrosine as a handle. The one component staple was investigated using acetyl-lysine and acetyl-tyrosine, while the two-component staple was investigated using acetylated-tyrosine 2,2'-(ethylenedioxy)bis(ethylamine). While model substrates proved to couple successfully under previously optimized conditions, concentration and characterization proved to be challenging for working with larger peptides. Additional experiments exploring the possibility of using tyrosine amination as a pH responding hydrogel are also described in this chapter. Finally, chapter five explores the possibility of synthesizing diphenylamines from phenol and ammonia formate as a convenient ammonia surrogate. Seventeen different diarylamines were synthesized with palladium on charcoal as the catalyst, with yields ranging from good to excellent. Notably, water and CO2 were the only byproducts generated from this transformation. Triphenylamine was also obtained in combination with the methodology described in Chapter 1"--
Book Synopsis THE DEVELOPMENT AND APPLICATION OF NEW PALLADIUM CATALYSTS IN CHALLENGING C-N AND C-O BOND FORMING REACTIONS. by : Christopher B. Lavery
Download or read book THE DEVELOPMENT AND APPLICATION OF NEW PALLADIUM CATALYSTS IN CHALLENGING C-N AND C-O BOND FORMING REACTIONS. written by Christopher B. Lavery and published by . This book was released on 2013 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Advances in Palladium-catalyzed Carbon-nitrogen Bond Forming Processes by : Rachel Elizabeth Tundel
Download or read book Advances in Palladium-catalyzed Carbon-nitrogen Bond Forming Processes written by Rachel Elizabeth Tundel and published by . This book was released on 2006 with total page 136 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter 1. Microwave-assisted, palladium-catalyzed C-N bond-forming reactions with aryl/heteroaryl nonaflates/halides and amines using the soluble amine bases DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or MTBD (7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene) and a catalyst system consisting of Pd2dba3 and ligands (XantPhos, 2-dicylcohexylphosphino-2',4',6'-triisopropyl-1,1 '-biphenyl (XPhos) and 2-di-tert-butylphosphino-2',4',6'-triisopropyl-1, '-biphenyl) resulted in good to excellent yields of arylamines in short reaction times. Chapter 2. Using a catalyst comprised of the bulky, electron-rich monophosphine ligand di-tert-Butyl XPhos (2-di-tert-butylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl) and Pd2dba3 with sodium tert-butoxide as the base, amino heterocycles were coupled successfully with aryl/heteroaryl halides in moderate to excellent yields.
Book Synopsis Advances in Late-Metal Carbon-Nitrogen Bond Formation for the Synthesis of Substituted Heterocycles by : Nicolas Rotta-Loria
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.
Book Synopsis Mechanistic Studies on Palladium-catalyzed Carbon-nitrogen Bond Forming Reactions by : Liane May Klingensmith
Download or read book Mechanistic Studies on Palladium-catalyzed Carbon-nitrogen Bond Forming Reactions written by Liane May Klingensmith and published by . This book was released on 2005 with total page 138 pages. Available in PDF, EPUB and Kindle. Book excerpt: Precatalyst species present in a solution of Pd2(dba)3 and Xantphos were identified as Pd(Xantphos)(dba) and Pd(Xantphos)2 by use of 31p NMR and independent syntheses. Pd(Xantphos)2 was found to form at high ligand concentrations. To determine whether the formation of this species affected reaction rates, reaction calorimetry was used to explore the rate of the palladium-catalyzed coupling of 4-t-butylbromobenzene and morpholine using the ligand Xantphos at varying palladium to ligand ratios. It was found that catalyst activity is dramatically dependent on the concentration of ligand relative to palladium, due to formation of Pd(Xantphos)2. Two plausible hypotheses for the low activity of Pd(Xantphos)2 as a precatalyst are (1) a slow rate of dissociation of a ligand from the bis-ligated species, and (2) the high degree of insolubility of Pd(Xantphos)2. Magnetization transfer experiments were used to probe the rate of dissociation of ligand for the bis-ligated species, and reaction calorimetry experiments were performed using the more soluble t-butylXantphos in comparison to Xantphos to determine whether the insolubility of' Pd(Xantphos)2 causes it to have relatively low activity. It was found that solubility is not the main cause for the low activity of Pd(Xantphos)2, and evidence was given to support the hypothesis that low activity results from the slow dissociation of a ligand from the bis-ligated species.
Book Synopsis Cross-coupling Reactions by : Joffrey Vrijdag
Download or read book Cross-coupling Reactions written by Joffrey Vrijdag and published by . This book was released on 2020 with total page 268 pages. Available in PDF, EPUB and Kindle. Book excerpt: "Cross-Coupling Reactions: An Overview opens with an overview of the fundamentals and applications of the young and fast developing area of transition metal catalyzed/mediated oxidative (dehydrogenative) C-H/C-H coupling reactions between two (hetero)arenes. Continuing, the authors highlight the recent advances regarding the ligand supported transition metal-catalyzed domino (cascade) or one-pot syntheses of various heterocycles involving cross-coupling reactions. The recent advances in Cu catalyzed tandem reactions for heterocycle synthesis are also addressed. Cu metal chemistry has garnered attention as a potential alternative to precious transition metals, being cheaper, more sustainable and more easily available. A comprehensive account of research on green chemical routes is provided, involving various palladium metal-based catalysts utilized in facilitating cross-coupling reaction in aqueous media. Reported decarboxylative cross-coupling reactions are discussed along with suitable examples, focusing on their mechanism of action"--
Book Synopsis Palladium Catalyzed Oxidation of Hydrocarbons by : P. Henry
Download or read book Palladium Catalyzed Oxidation of Hydrocarbons written by P. Henry and published by Springer Science & Business Media. This book was released on 2012-12-06 with total page 449 pages. Available in PDF, EPUB and Kindle. Book excerpt: The field of organometallic chemistry has emerged over the last twenty-five years or so to become one of the most important areas of chemistry, and there are no signs of abatement in the intense current interest in the subject, particularly in terms of its proven and potential application in catalytic reactions involving hydrocarbons. The development of the organometallic/ catalysis area has resulted in no small way from many contributions from researchers investigating palladium systems. Even to the well-initiated, there seems a bewildering and diverse variety of organic reactions that are promoted by palladium(II) salts and complexes. Such homogeneous reactions include oxidative and nonoxidative coupling of substrates such as olefins, dienes, acetylenes, and aromatics; and various isomerization, disproportionation, hydrogenation, dehydrogenation, car bonylation and decarbonylation reactions, as well as reactions involving formation of bonds between carbon and halogen, nitrogen, sulfur, and silicon. The books by Peter M. Maitlis - The Organic Chemistry of Palladium, Volumes I, II, Academic Press, 1971 - serve to classify and identify the wide variety of reactions, and access to the vast literature is available through these volumes and more recent reviews, including those of J. Tsuji [Accounts Chem. Res. , 6, 8 (1973); Adv. in Organometal. , 17, 141 (1979)], R. F. Heck [Adv. in Catat. , 26, 323 (1977)], and ones by Henry [Accounts Chem. Res. , 6, 16 (1973); Adv. in Organometal. , 13, 363 (1975)]. F. R. Hartley's book - The Chemistry of Platinum and Palladium, App!. Sci. Pub!.
Book Synopsis Development of C-C and C-N Bond Forming Reactions Utilizing Palladium Carbene Intermediates and Reaction Predictor by : Eugene Gutman
Download or read book Development of C-C and C-N Bond Forming Reactions Utilizing Palladium Carbene Intermediates and Reaction Predictor written by Eugene Gutman and published by . This book was released on 2017 with total page 242 pages. Available in PDF, EPUB and Kindle. Book excerpt: The research described herein consists of two disparate areas of study. The first and largest portion describes the development of novel palladium-catalyzed C-C and C-N bond forming reactions. The second portion describes the development of the Reaction Predictor system and its application towards identification of reaction products and pathways.Palladium-carbenes are important intermediates in many modern C-C and C-heteroatom bond forming reactions. Palladium-catalyzed carbenylative coupling reactions are analogous to carbonylative processes with carbon monoxide. Insertion of a cis X type ligand into the palladium-carbene can potentially generate a new stereogenic center, making these reactions worthy of study. Carbenylative insertions have been used to generate electrophilic eta3-allylpalladium species which were trapped with nitrogen and carbon nucleophiles. This work describes the cyclization of eta3-benzylpalladium species derived from palladium-catalyzed carbenylative insertion. This optimization and broad substrate scope of this reaction led to the synthesis of 1-arylindanes and 1-aryltetralins in high yields. Additionally, this reaction was used to prepare tetralone 2.30bl, a synthetic intermediate in the Curran synthesis of (+/-)-podophyllotoxin. The carbenylative cyclization also led us to pursue utilizing aliphatic N-tosylhydrazones as palladium-carbene precursors in other coupling reactions. It was realized that aliphatic N-tosylhydrazones with adjacent hydrogens can effectively participate in three-component palladium-catalyzed carbenylative cross-coupling reactions of vinyl iodides while avoiding beta-hydride elimination.Development of a palladium-catalyzed enantioselective carbene insertion into the N-H bond of aromatic heterocycles to obtain alpha-(N-indolyl)-alpha-arylesters and alpha-(N-carbazolyl)-alpha-arylesters, using alpha-diazo-alpha-arylacetates as palladium carbene precursors is also described. Aliphatic amines were also competent coupling partners in the reaction, affording biologically active piperdine derivatives in moderate yields. The reaction was applied towards the synthesis of a bioactive carbazole derivative in a concise manner.In a separate project an inductive machine learning reaction prediction program called Reaction Predicator has been trained and applied towards identification of plausible reaction products in ESI spectra. The reaction predictor training set has been expanded by the addition of new reactions written in our lab. Over 800 transition metal based training reactions have been written.In addition, over 10,000 new complex training reactions have been written and added to the training set. The Reaction Predictor pathway search feature has been customized to match products to unknown m/z peaks in ESI spectra. Pathway search was applied towards unknown identification in palladium-catalyzed N-H insertion reactions.
Book Synopsis Applied Cross-Coupling Reactions by : Yasushi Nishihara
Download or read book Applied Cross-Coupling Reactions written by Yasushi Nishihara and published by Springer Science & Business Media. This book was released on 2012-12-14 with total page 247 pages. Available in PDF, EPUB and Kindle. Book excerpt: “Applied Cross-Coupling Reactions” provides students and teachers of advanced organic chemistry with an overview of the history, mechanisms and applications of cross-coupling reactions. Since the discovery of the transition-metal-catalyzed cross-coupling reactions in 1972, numerous synthetic uses and industrial applications have been developed. The mechanistic studies of the cross-coupling reactions have disclosed that three fundamental reactions: oxidative addition, transmetalation, and reductive elimination, are involved in a catalytic cycle. Cross-coupling reactions have allowed us to produce a variety of compounds for industrial purposes, such as natural products, pharmaceuticals, liquid crystals and conjugate polymers for use in electronic devices. Indeed, the Nobel Prize for Chemistry in 2010 was awarded for work on cross-coupling reactions. In this book, the recent trends in cross-coupling reactions are also introduced from the point of view of synthesis design and catalytic activities of transition-metal catalysts.
Book Synopsis Cross-Coupling Reactions by : Norio Miyaura
Download or read book Cross-Coupling Reactions written by Norio Miyaura and published by Springer. This book was released on 2003-07-01 with total page 253 pages. Available in PDF, EPUB and Kindle. Book excerpt: In 1972, a very powerful catalytic cycle for carbon-carbon bond formation was 2 first discovered by the coupling reaction of Grignard reagents at the sp -carbon. Over the past 30 years, the protocol has been substantially improved and expanded to other coupling reactions of Li,B,N,O,Al,Si,P,S,Cu,Mn,Zn,In,Sn, and Hg compounds. These reactions provided an indispensable and simple methodology for preparative organic chemists. Due to the simplicity and rel- bility in the carbon-carbon, carbon-heteroatom, and carbon-metalloid bo- formations,as well as high efficiency of the catalytic process,the reactions have been widely employed by organic chemists in various fields. Application of the protocol ranges from various syntheses of complex natural products to the preparation of biologically relevant molecules including drugs, and of sup- molecules, and to functional materials. The reactions on solid surfaces allow robot synthesis and combinatorial synthesis. Now, many organic chemists do not hesitate to use transition metal complexes for the transformation of org- ic molecules. Indeed, innumerable organic syntheses have been realized by the catalyzed reactions of transition metal complexes that are not achievable by t- ditional synthetic methods. Among these, the metal-catalyzed cross-coupling reactions have undoubtedly contributed greatly to the development of such a new area of “metal-catalyzed organic syntheses”. An excellent monograph for the cross-coupling reactions and other met- catalyzed C-C bond-forming reactions recently appeared in Metal-catalyzed Cross-coupling Reactions (Wiley-VCH,1998).
Book Synopsis Catalytic Methods for Carbon-carbon and Carbon-nitrogen Bond Formation by : Stephen David Ramgren
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.
Book Synopsis Palladium Catalyzed Carbon-carbon Bond Formation at Carbon-hydrogen Bonds by : Louis-Charles Campeau
Download or read book Palladium Catalyzed Carbon-carbon Bond Formation at Carbon-hydrogen Bonds written by Louis-Charles Campeau and published by . This book was released on 2008 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: The biaryl core has been identified by medicinal chemists as a privileged structure in pharmaceutical compounds as it is found in 4.3% of all drugs. For over a century, synthetic chemists have sought new methods for their preparation. Breakthroughs in synthetic catalytic methodology over the past thirty years gave rise to now routine reactions such as the Suzuki and Stille couplings. Unfortunately, the need for pre-activation of both coupling partners makes for wasteful installation and subsequent removal of activating agents. Direct arylation reactions are attractive alternatives to traditional cross-coupling methods, as one of the pre-activated partners is replaced with a simple arene. The organometallic coupling partner is typically replaced as it is the most difficult to prepare. Although the advantages of this approach have made it a popular research topic for more than twenty-five years, no general catalysts exist for this transformation, and in a lot of cases reactivity remains a challenge. This thesis will outline our work in this area of research. First, our efforts toward the development of a general catalyst for the intramolecular direct arylation of aryl halides with simple arenes will be presented. These studies led to the development of three new catalysts for this transformation, affording a process general for aryl chlorides, bromides and iodides. Additionally, mechanistic studies performed on this system have brought to the forefront the concerted metallation-deprotonation mechanistic model for direct arylation. Ultimately, these studies led to the first non-directed intermolecular direct arylation of a simple arene. In a second section, efforts toward the inclusion of pi-deficient heteocycles as a substrate class in direct arylation will be outlined. These studies led to the development of a novel cross-coupling reaction of azine N-oxides with aryl halides. Greater mechanistic understanding, made possible through the use of computational tools, was crucial in extending this methodology to azole N-oxides. Finally, the development of novel direct functionalization reactions with picoline derivatives is described. These substrates are among the first to be suitable for catalyst controlled site-selective functionalization of a sp2 or sp3 C-H bond.
Book Synopsis Palladium-catalyzed C-N Cross-coupling Reactions Toward the Synthesis of Drug-like Molecules by : Camille Z. McAvoy
Download or read book Palladium-catalyzed C-N Cross-coupling Reactions Toward the Synthesis of Drug-like Molecules written by Camille Z. McAvoy and published by . This book was released on 2012 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The development of methodologies for C-N bond formation reactions is an important scientific challenge because of many academic and industrial applications. This work will focus particularly on palladium-catalyzed cross-couplings of amine-containing compounds with aryl halides. The scope of the BrettPhos precatalyst for the cross-coupling of ortho-substituted aryl iodides with amides is studied using substrates with a variety of functional groups. Due to potential metal-chelating issues with some of the substrates used in this study, a proposed ligand synthesis is discussed in which one of the methoxy groups of BrettPhos is replaced with a morpholine capable of occupying palladium's open coordination site during its catalytic cycle. A final C-N bond formation study focuses on the cross-coupling of aryl halides with amidine salts. For this cross-coupling, a methodology has been developed that can be applied to various electron-rich, electron-poor, and electron-neutral substrates. Furthermore, the products of this cross-coupling can be used for a subsequent electrocyclization through a reaction with aldehyde, demonstrating that a relatively simple two-pot methodology can be used to make relatively complex substrates with pharmaceutical applications. Both amides and amidines are common moieties in drug-like molecules because of the various biological activities of these functional groups. Potential medicinal applications of the developed cross-coupling of amidine salts with aryl halides methodology are described. Thus, methodologies for various palladium-catalyzed, C-N cross-couplings as well as a potential ligand synthesis to be used for palladium catalysis are herein discussed.
Book Synopsis Comprehensive Organometallic Chemistry II by : Richard J. Puddephatt
Download or read book Comprehensive Organometallic Chemistry II written by Richard J. Puddephatt and published by Elsevier. This book was released on 1995 with total page 670 pages. Available in PDF, EPUB and Kindle. Book excerpt:
