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Abstract: Cross-coupling reactions have been of interest to organic chemists much of the past century. It has only been in the last half century that prominent advances have been discovered, all of which take advantage of organometallic chemistry. The most widely explored reactions use palladium or nickel complexes to promote the cross-coupling of a wide variety of functionalized aryl groups. One such reaction is the Suzuki-Miyaura cross-coupling, which is a transition-metal mediated coupling of an organohalide and an organoborane. As a carbon-carbon bond forming reaction, the Suzuki-Miyaura cross-coupling has great potential in synthetic applications due to its mild conditions and functional group tolerance. An important aspect of the reaction is the ability to impart specific configurations during the formation of new carbon-carbon bonds. Such selectivity has been thoroughly explored in the Suzuki-Miyaura cross-coupling of sp2-sp2 carbon-carbon bonds with the retention of E or Z stereochemistry. However, the formation of axially chiral biaryls still presents an ongoing challenge. Biaryls containing at least three substituents ortho to the aryl-aryl bond exhibit atropisomerism, which gives rise to axial chirality. Thus, the application of asymmetric catalysis to the formation of axial chiral biaryls was of interest. The work presented in this thesis investigates the synthesis of several chiral ligands for use in cross-coupling reactions and a study of the Suzuki-Miyaura cross-coupling of biaryls.
This book is a printed edition of the Special Issue "Suzuki–Miyaura Cross-Coupling Reaction and Potential Applications" that was published in Catalysts
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
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.
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).
In Science of Synthesis: Cross Coupling and Heck-Type Reactions, expert authors present and discuss the best and most reliable methods currently available for the formation of new carbon-carbon and carbon-heteroatom bonds using these reactions, highlighted with representative experimental procedures. Together, the three volumes of Cross Coupling and Heck-Type Reactions provide an extensive overview of the current state of the art in this field of central importance in modern chemistry, and are an invaluable resource for the practicing synthetic organic chemist. This volume covers carbon-carbon bond formation, and, as a widely acknowledged recognition of the importance of the transformations described herein, virtually all of the chemistry described in this volume has achieved "Name Reaction" stature, and the chapters are organized accordingly. Thus, Suzuki-Miyaura reactions, Hiyama cross coupling, Stille coupling, Negishi coupling, and finally Kumada coupling are discussed in sequence, with a particular emphasis on breadth of scope rather than detailed minutiae. This volume is part of a 3-volume set: Cross Coupling and Heck-Type Reactions Workbench Edition General information about Science of Synthesis