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This book is a printed edition of the Special Issue "Suzuki–Miyaura Cross-Coupling Reaction and Potential Applications" that was published in Catalysts
“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.
On the contrary, flow continuous processes present a series of advantages leading to new ways to synthesise chemical products.
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).
Palladium-Catalyzed Modification of Nucleosides, Nucleotides and Oligonucleotides describes the procedures and protocols related to the modification of nucleosides, nucleotides and oligonucleotides via Pd-mediated cross-coupling processes. The book highlights the growing area of nucleic acid modification and how Pd-mediated coupling reactions can assist this development. Users will find key synthetic protocols for these reactions in this latest volume in the Latest Trends in Palladium Chemistry series. As most of the research in the field of antiviral agents has centered on the use of modified nucleosides that have exhibited promising activity, this book provides an up-to-date reference for both professionals in industry and other interested parties. Provides synthetic routes for useful nucleoside molecules, information otherwise found only through time-consuming literature searches Covers metal-mediated and metal-catalyzed cross coupling processes of nucleosides and related compounds Includes Suzuki-Miyaura, Stille and Sonogashira reactions, as well as C-H bond functionalization Highlights the growing area of nucleic acid modification and how Pd-mediated coupling reactions can assist
This valuable and unique text, written by world-renowned researchers, covers the application of these reagents to organic synthesis. The book is written in a clear and concise manner, containing step-by-step experimental procedures, and should be a valuable resource to new postgraduate students and experienced researchers alike.
Synthetic Methods in Drug Discovery Volume 1 focusses on the hugely important area of transition metal mediated methods used in industry. Current methods of importance such as the Suzuki-Miyaura coupling, Buchwald-Hartwig couplings and CH activation are discussed. In addition, exciting emerging areas such as decarboxylative coupling, and the uses of iron and nickel in coupling reactions are also covered. This book provides both academic and industrial perspectives on some key reactions giving the reader an excellent overview of the techniques used in modern synthesis. Reaction types are conveniently framed in the context of their value to industry and the challenges and limitations of methodologies are discussed with relevant illustrative examples. Edited and authored by leading scientists from both academia and industry, this book will be a valuable reference for all chemists involved in drug discovery as well as postgraduate students in medicinal chemistry.
The amide bond represents a privileged motif in chemistry. The recent years have witnessed an explosion of interest in the development of new chemical transformations of amides. These developments cover an impressive range of catalytic N–C bond activation in electrophilic, Lewis acid, radical, and nucleophilic reaction pathways, among other transformations. Equally relevant are structural and theoretical studies that provide the basis for chemoselective manipulation of amidic resonance. This monograph on amide bonds offers a broad survey of recent advances in activation of amides and addresses various approaches in the field.
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.