Author: Publisher:
ISBN:
Category :
Languages : en
Pages : 450
Book Description
Synthesis of Fused Heterocycles by Sequential Palladium Catalyzed Cross-coupling Reactions
Author: Synthesis and Modification of Heterocycles by Metal-Catalyzed Cross-coupling Reactions
Author: Tamás PatonayPublisher: Springer
ISBN: 3319326104
Category : Science
Languages : en
Pages : 371
Book Description
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.
Synthesis of Aromatic Heterocycles and Carbocycles Through Tandem Palladium-Catalyzed Cross-Coupling Reactions of Gem-dihaloolefins
Author: Christopher Scott BryanPublisher:
ISBN:
Category :
Languages : en
Pages : 798
Book Description
Our group has developed a strategy for the synthesis of benzofused carbocycles and heterocycles through tandem palladium-catalyzed reactions of gem-dibromoolefins. In these syntheses, one bromide undergoes a Pd-catalyzed cyclization reaction, and the other participates in an orthogonal inter- or intramolecular Pd-catalyzed reaction to functionalize or annulate that ring, respectively.Chapter 2 describes the synthesis of benzothiophenes through the combination of a Pd-catalyzed C--S coupling with an orthogonal Suzuki, Heck, or Sonogashira reaction. This represents the first example of the incorporation of Pd-catalyzed C--S coupling into a tandem reaction.Chapter 1 describes the pairing of an intramolecular C--N bond forming reaction (the Buchwald- Hartwig coupling) with an intramolecular direct arylation for the synthesis of fused indole derivatives. A range of previously unknown heterocycles were synthesized through this method.In Chapter 3, a tandem intramolecular Heck / intermolecular Suzuki reaction is described for the synthesis of methyleneindenes. Studies on this reaction have provided advanced understanding of the mechanism, including how variation of the ligand controls the regioselectivity of the reaction.
Heterocycles from Double-Functionalized Arenes
Author: Xiao-Feng WuPublisher: Royal Society of Chemistry
ISBN: 1782621369
Category : Science
Languages : en
Pages : 315
Book Description
An introduction to transition metal catalyzed coupling reactions of double-functionalized arenes in heterocycle synthesis.
Norbornene-mediated Palladium-catalyzed Synthesis of Fused Aromatic Carbocycles and Heterocycles /by Dino Alberico
Author: Dino AlbericoPublisher:
ISBN: 9780494157459
Category :
Languages : en
Pages : 748
Book Description
Chapter 2 examines a sequence in which two alkyl-aryl bonds and one alkenyl/aryl bond are formed in one pot. The reaction conditions were optimized and the scope was examined. A variety of symmetrical and unsymmetrical tricyclic heterocycles were synthesized in good yields from a Heck acceptor and an aryl iodide containing two tethered alkyl bromides. This methodology was applied to the synthesis of a tricyclic mescaline analogue. We have developed a norbornene-mediated palladium-catalyzed tandem reaction for the preparation of fused aromatic carbocycles and heterocycles. Chapter 1 describes an alkylation/alkenylation sequence using aryl iodides and bromoenoates. The effect of substitution on the bromoenoate was evaluated. A wide variety of carbon-, oxygen-, and nitrogen-containing functional groups are tolerated allowing for rapid access to highly functionalized aromatic carbocycles. Chapter 3 describes an alkylation/C-H functionalization sequence. In this highly efficient approach, an alkyl-aryl bond and an aryl-heteroaryl bond are created from two C-H bonds in a one-pot process. A wide range of functionalized annulated indoles were synthesized in a convergent manner in high yields.
Palladium-Catalyzed Coupling Reactions
Author: Árpád MolnárPublisher: John Wiley & Sons
ISBN: 3527648305
Category : Science
Languages : en
Pages : 531
Book Description
This handbook and ready reference brings together all significant issues of practical importance in selected topics discussing recent significant achievements for interested readers in one single volume. While covering homogeneous and heterogeneous catalysis, the text is unique in focusing on such important aspects as using different reaction media, microwave techniques or catalyst recycling. It also provides a comprehensive treatment of key issues of modern-day coupling reactions having emerged and matured in recent years and emphasizes those topics that show potential for future development, such as continuous flow systems, water as a reaction medium, and catalyst immobilization, among others. With its inclusion of large-scale applications in the pharmaceutical industry, this will equally be of great interest to industrial chemists. From the contents * Palladium-Catalyzed Cross-Coupling Reactions - A General Introduction * High-turnover Heterogeneous Palladium Catalysts in Coupling Reactions: the Case of Pd Loaded on Dealuminated Y Zeolites Palladium-Catalyzed Coupling Reactions with Magnetically Separable Nanocatalysts * The Use of Ordered Porous Solids as Support Materials in Palladium-Catalyzed Cross-Coupling Reactions * Coupling Reactions Induced by Polymer-Supported Catalysts * Coupling Reactions in Ionic Liquids * Cross-Coupling Reactions in Aqueous Media * Microwave-Assisted Synthesis in C-C and C-Heteroatom Coupling Reactions * Catalyst Recycling in Palladium-Catalyzed Carbon-Carbon Coupling Reactions * Nature of the True Catalytic Species in Carbon-Carbon Coupling Reactions with * Heterogeneous Palladium Precatalysts * Coupling Reactions in Continuous Flow Systems * Large-Scale Applications of Palladium-Catalyzed Couplings in the Pharmaceutical Industry
Catalyzed Carbon-Heteroatom Bond Formation
Author: Andrei K. YudinPublisher: John Wiley & Sons
ISBN: 3527633405
Category : Science
Languages : en
Pages : 541
Book Description
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.
Palladium Assisted Synthesis of Heterocycles
Author: Navjeet KaurPublisher: CRC Press
ISBN: 1351242598
Category : Medical
Languages : en
Pages : 482
Book Description
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.
Metal-catalyzed Cross-coupling Reactions
Author: François DiederichPublisher: John Wiley & Sons
ISBN: 3527612203
Category : Science
Languages : en
Pages : 540
Book Description
Carbon-carbon bond forming reactions are arguably the most important processes in chemistry, as they represent key steps in the building of complex molecules from simple precursors. Among these reactions, metal-catalyzed cross-coupling reactions are extensively employed in a wide range of areas of preparative organic chemistry, ranging from the synthesis of complex natural products, to supramolecular chemistry, and materials science. In this work, a dozen internationally renowned experts and leaders in the field bring the reader up to date by documenting and critically analyzing current developments and uses of metal-catalyzed cross-coupling reactions. A particularly attractive and useful feature, that enhances the practical value of this monograph, is the inclusion of key synthetic protocols, in experimental format, chosen for broad utility and application. This practice-oriented book can offer the practitioner short cuts to ensure they remain up-to-date with the latest developments.
Copper and Palladium Catalyzed Benz-fused Heterocycle Synthesis Via Intramolecular Cross-Coupling and C---H Bond Functionalization Strategies
Author: Laurie Lynn JoycePublisher:
ISBN:
Category :
Languages : en
Pages : 906
Book Description
This thesis is a summary of research conducted in the laboratory of Professor Robert A. Batey at the University of Toronto. The manuscript is divided into three chapters.Chapter one gives a general overview of methods for metal-catalyzed synthesis of heterocycles through carbon-heteroatom (C--Y) bond-forming events.Chapter two describes the intramolecular copper-catalyzed synthesis of 2aminobenzoxazoles through the coupling of aryl bromides with ureas. Reaction conditions were optimized through studies examining the effect of changing various reaction parameters including temperature, catalyst and ligand loadings, solvent choice, and degree of dryness of the reaction system. Optimized reaction conditions involve heating o-bromophenylurea precursors with 10 mol% copper iodide and 20 mol% 1,10-phenanthroline ligand in the presence of the weak base CS2CO3 (1.2 equiv) in a 1:1 acetonitrile:xylenes solvent system at 110-120°C to give 2-aminobenzoxazole products in good to excellent conversions and yields for a reaction time of 24 hours, These reactions were found to require strictly anhydrous reaction conditions and are effective only for N,N',N'-trisubstituted o-bromophenylureas.Chapter three describes a novel paliadium(0) catalyzed intramolecular oxidative C--H bond functionalization/C--S bond formation reaction for the synthesis of 2aminobenzothiazoles and related heterocycles. Reaction optimization studies were conducted by examining the effect of changing various reaction parameters while monitoring the progress of the reactions using HPLC. Optimized reaction conditions involve heating arylthiourea substrates with 3 mol% palladium tetrakistriphenylphosphine with activated 10 mol% manganese dioxide in acetonitrile solvent under an oxygen atmosphere at 80°C to give cyclized 2-aminobenzothiazole products in excellent yields. Anhydrous reaction conditions are required, and only N,N',N'-trisubstituted phenylthioureas were found to be suitable precursors to 2aminobenzothiazoles. This methodology offers improved efficiency and atom economy over previous metal-catalyzed methods that require ortho-halo arylthiourea precursors, thereby significantly improving the availability of phenylthiourea starting materials. Unlike for other palladium-catalyzed C--H functionalization reactions typically utilizing Pd(II) and a co-oxidant such as Cu(OAc)2 under oxidative conditions, we propose that the main role of activated MnO 2 is to act as a porous surface/sink to adsorb oxygen and deliver it to paliadium(0) to form a peroxo-paliadium(II) species.