Synthesis of Heterocycles Via Palladium-catalyzed Coupling of Vinylic Halides and Functionally-substituted Alkenes PDF Download

Author: Hoseok Yang
Publisher:
ISBN:
Category :
Languages : en
Pages : 342

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Author: Maria Gerelle
Publisher:
ISBN:
Category :
Languages : en
Pages :

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Book Description
Chapter 1 is a brief literature review of the most recent progress in the area of C-H functionalization via palladium catalysis. This covers the functionalization of electron deficient arenes and heterocycles with alkenyl and alkyl halides both using inter- and intra-molecular reactions. The chapter also contains an overview of recent work from the Willis group. Chapter 2 presents the functionalization of electron deficient arenes and alkenyl bromides using palladium catalysis (Scheme 1), as well as the use of statistical analysis software for optimizing the cross-coupling reaction. Scheme 1: Functionalization of electron deficient arenes using palladium catalysis Chapter 3 describes the cross-coupling of substituted benzoxazoles, benzothiazole and benzimidazole with a range of alkenyl iodides using palladium catalysis (Scheme 2). The reaction can tolerate both (E) and (Z) disubstituted alkenes and tri-substituted alkenyl iodides, with retention of the double bond geometry. 1 x =0, S, NMe - 14 examples 25-99% yield i Scheme 2: Cross-coupling using benzoxazoles, benzothiazole and benzimidazole with alkenyl iodides Chapter 4 details the synthesis of sultams via an intramolecular functionalization using palladium catalysis. The chapter covers the optimization of the starting material synthesis as well as the cross-coupling reaction. We can access the sulfonamides from cyc1ohexenone and were able to incorporate a large range of substitution patterns (Scheme 3). Scheme 3: Synthesis ofsultams from cyclohexenone Finally, Chapter 5 contains all the experimental details, general considerations and compound data. All the NMR spectra of novel compounds can be found in the appendix. 2.

Author: Navjeet Kaur
Publisher: CRC Press
ISBN: 1351242601
Category : Medical
Languages : en
Pages : 432

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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.

Author: John P. Wolfe
Publisher: Springer
ISBN: 3642388809
Category : Science
Languages : en
Pages : 276

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Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Carboamination or Carboalkoxylation Reactions, by John P. Wolfe Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Diamination, Aminoalkoxylation, or Dialkoxylation Reactions, by Sherry R. Chemler Synthesis of Heterocycles via Metal-Catalyzed Wacker-Type Oxidative Cyclization Reactions of Alkoxy- or Amino-Alkenes, by Wanbin Zhang Synthesis of Saturated Heterocycles via Metal-Catalyzed Hydroamination or Hydroalkoxylation Reactions, by Lisa D. Julian Synthesis of Saturated Heterocycles via Metal-Catalyzed Allylic Alkylation Reactions, by Aaron Aponick Synthesis of Heterocycles via Metal-Catalyzed Cascade/Domino Reactions that Generate a C–N or C–O Bond, by Mark Lautens Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions that Generate a C–N or C–O Bond, by Jerome Waser

Author:
Publisher:
ISBN:
Category : Dissertations, Academic
Languages : en
Pages : 868

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Author: Xiao-Feng Wu
Publisher: Royal Society of Chemistry
ISBN: 1782623124
Category : Science
Languages : en
Pages : 314

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Book Description
The efficient synthesis of heterocycles has become one of the main branches in organic chemistry due to their use in the synthesis of natural products and pharmaceuticals. Current sythentic strategies based on C-H activation methodologies are met with many problems like harsh reaction conditions and low reaction efficiency. Double functionalized chemicals offer a perfect alternative for the synthesis of heterocycles. Heterocycles from Double-Functionalized Arenes starts with a short discussion on the importance of heterocycles and a brief introduction on the preparation of double-functionalized arenes. Specific chapters then look at five-membered heterocycles synthesis, six-membered heterocycles synthesis and macroheterocycles synthesis. This is the first book dedicated to the topic of transition metal catalyzed coupling reactions of double functionalized arenes in heterocycle synthesis and can be used as a handbook for senior researchers and as an introduction for organic chemistry students.

Author: David A. Petrone
Publisher: Springer
ISBN: 3319775073
Category : Science
Languages : en
Pages : 392

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This book investigates the use of palladium modified by bulky ligands as catalysts for new chemical transformations that rapidly assemble several classes of complex heterocyles. It documents the development of new chemical reactions involving carbon–carbon (C‒C) and carbon–halogen (C‒X) bond formation in the context of alkene difunctionalization and dearomatization reactions. Due to the ubiquity of heterocycles in bioactive natural products and life-improving pharmaceutical treatments, a long-term goal for synthetic organic chemists has been to develop novel and creative heterocycle syntheses that illicit a high degree of product diversity and are characterized by mild reaction conditions and limited waste production. A considerable fraction of leading pharmaceutical drugs contain at least one heterocycle within their chemical structure, and their prevalence in these technologies is strong evidence that the fundamental curiosities of organic chemistry lead to real-world solutions for the health and wellness of the global population.

Author: Jie Jack Li
Publisher: Gulf Professional Publishing
ISBN: 0080914411
Category : Science
Languages : en
Pages : 1011

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Book Description
Palladium chemistry, despite its immaturity, has rapidly become an indispensable tool for synthetic organic chemists. Heterocycles are of paramount importance in the pharmaceutical industry and palladium chemistry is one of the most novel and efficient ways of making heterocycles. Today, palladium-catalyzed coupling is the method of choice for the synthesis of a wide range of biaryls and heterobiaryls. The number of applications of palladium chemistry to the syntheses of heterocycles has grown exponentially. These developments highlight the need for a monograph dedicated solely to the palladium chemistry in heterocycles and this book provides a comprehensive explanation of the subject. The principal aim of Palladium in Heterocyclic Chemistry is to highlight important palladium-mediated reactions of heterocycles with emphasis on the unique characteristics of individual heterocycles. 1. Palladium chemistry of heterocycles has its "idiosyncrasies" stemming from their different structural properties from the corresponding carbocyclic aryl compounds. Even activated chloroheterocycles are sufficiently reactive to undergo Pd-catalyzed reactions. As a consequence of &agr and &bgr activation of heteroaryl halides, Pd-catalyzed chemistry may take place regioselectively at the activated positions, a phenomenon rarely seen in carbocyclic aryl halides. In addition, another salient peculiarity in palladium chemistry of heterocycles is the so-called "heteroaryl Heck reaction". For instance, while intermolecular palladium-catalyzed arylations of carbocyclic arenes are rare, palladium-catalyzed arylations of azoles and many other heterocycles readily take place. Therefore, the principal aim of this book is to highlight important palladium-mediated reactions of heterocycles with emphasis on the unique characteristics of individual heterocycles. 2. A myriad of heterocycles are biologically active and therefore of paramount importance to medicinal and agricultural chemists. Many heterocycle-containing natural products (they are highlighted in boxes throughout the text) have elicited great interest from both academic and industrial research groups. Recognizing the similarities between the palladium chemistry of arenes and heteroarenes, a critical survey of the accomplishments in heterocyclic chemistry will keep readers abreast of such a fast-growing field. We also hope this book will spur more interest and inspire ideas in such an extremely useful area. This book comprises a compilation of important preparations of heteroaryl halides, boranes and stannanes for each heterocycle. The large body of data regarding palladium-mediated polymerization of heterocycles in material chemistry is not focused here; neither is coordination chemistry involving palladium and heterocycles. Many heterocycle-containing natural products (highlighted throughout the text) have elicited great interest from both academic and industrial research groups. Recognizing the similarities between the palladium chemistry of arenes and heteroarenes, a critical survey of the accomplishments in heterocyclic chemistry keeps readers abreast of this fast-growing field. It is also hoped that this book will stimulate more interest and inspire new ideas in this exciting field. Contains the most up-to-date developments in this fast-moving field Includes 3 new chapters Contains material from selected well-respected authors on heterocyclic chemistry

Author: Adam Gerherd). Meyer
Publisher:
ISBN:
Category :
Languages : en
Pages : 360

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Studies the synthesis of substituted hydraxy and amino vinyl triflates and their applicability to undergo an intramolecular palladium-catalyzed carbonylation reaction. Optically active monocyclic and bicyclic [alpha], [beta]-unsaturated [ga-lactones and the monoterpene(+) mintlactone were synthesized.

Author: Norio Miyaura
Publisher: Springer
ISBN: 354045313X
Category : Science
Languages : en
Pages : 253

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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).