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This volume presents recent progress on 3d base metal catalyzed C-C cross coupling reactions. The contributions provide detailed discussions on the use of cheap metal catalysts such as Cr, Mn, Fe, Co, Ni, Cu, and Zn to construct Csp2-Csp2, Csp2-Csp3 and Csp3-Csp3 bonds with a variety of substrates. These non-noble metal catalyst have many advantages such as being inexpensive, having low toxicity and are environmentally benign. Therefore the use of cheap metal catalysts in organic synthesis has gained much attention in efforts to develop more sustainable synthetic green chemistry. Each chapter is written by international experts in the field and is a great resource for students, researchers and chemists working in industry to gain an overview on the latest developments.
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).
Organozinc reagents are less reactive than Grignard reagents but they are much more chemoselective. Since the Negishi cross-coupling reaction developed by Ei-ichi Negishi, who was awarded the Nobel Price in chemistry in 2010, a number of cross-coupling reactions involving organozinc derivatives and transition metal catalysts (Pd, Ni, Fe, Co, Cu, ...) has been tuned up to form C-C bonds. This book on "Organozinc derivatives and transition metal catalysts" has been written by experts in the field and is a complement to the book entitled "Grignard reagents and transition metal catalysts" (a De Gruyter book, edited by J. Cossy). Grignard reagents or organozinc reagents, that is the question? From a given substrate, what is the best organometallic reagent and the best transition metal to form a C-C bond by using a cross-coupling reaction? The solution might be found in these two books.
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.
This three volume book is the follow-up handbook to the bestselling volume "Metal-Catalyzed Cross-Coupling Reactions", the definitive reference in the field. In line with the enormous developments in this area, this is not a new edition, but rather a new book in three volumes with over 50% more content. This new content includes C-H activation, shifting the focus away from typical cross-coupling reactions, while those topics and chapters found in de Meijere/Diederich's book have been updated and expanded. With its highly experienced editor team and the list of authors reading like an international Who's-Who in the field, this work will be of great interest to every synthetic chemist working in academia and industry.
Following on from its recognition in the 2010 Nobel Prize for Chemistry, contributors from across the globe present the latest cross-coupling trends in both academia and industry.
Transition metal-catalyzed cross-coupling reactions have proved to be powerful tools for carbon-carbon as well as carbon-heteroatom bond formation in the development of synthetic methodologies for applications ranging from pharmaceuticals to materials. This book, consisting of an editorial, two reviews and two articles, focuses on recent promising research and novel trends in the field of cross-coupling reactions, employing a range of different catalysts. A review by Kostas and Steele provides a survey of the research in the area of cross-coupling catalytic reactions with transition metal complexes based on the thiosemicarbazone unit and a discussion of the prospects for future developments. Another review by Polychronopoulou, Shaya and co-authors describes the progress made over the 21st century concerning the utilization of C(sp3)-organoboranes as partners in metal-catalyzed C(sp3)-C(sp2) cross-couplings, such as B-alkyl Suzuki-Miyaura reactions. The article by Waldvogel, Breinbauer and co-authors demonstrates for the first time the synthetic potential of combining the electro-oxidative dehydrogenative cross coupling of ortho-substituted phenols with Pd-catalyzed cross-coupling reactions. In the second article, Stĕpnička and co-workers describe the preparation of palladium catalysts deposited over silica gel-bearing composite amide-donor functional moieties on the surface, which were evaluated in the Sonogashira-type cross-coupling of acyl chlorides with terminal alkynes.
"Iron catalyzed C-C cross coupling reactions have drawn significant interest as more versatile and cost effective alternatives to traditional precious metal catalysts, however limited mechanistic understanding of these reactions has been reported hindering rational optimization of these systems. The use of electron paramagnetic resonance, magnetic circular dichroism, Ms̲sbauer spectroscopy, and density functional theory, in addition to GC, NMR, and X-ray crystallography, are applied in the examination of structural and mechanistic aspects of in situ iron cross-coupling chemistry with a focus on elucidating how different nucleophiles, reaction additives and protocols affect reactivity. In Chapter 2 and 3, initial studies presented investigate iron-bisphosphine catalyzed cross-coupling of aryl nucleophiles with alkyl halides. These studies describe the iron species formed in situ and provide insight into the active species of catalysis as a function of nucleophile in both Kumada and Suzuki-Miyaura cross-coupling reactions. In Chapter 4, further studies investigate simple iron salt catalysts with methyl and ethyl Grignards for direct determination of iron species present in solution and their reactivity with electrophile. Additional studies further probe the effect of N-methylpyrrolidone as a co-solvent. In conclusion, it is shown in these studies the novel utility of these direct spectroscopic probes in monitoring in situ iron speciation and reactivity with electrophile. Furthermore, through monitoring of reactions we can also define why key aspects of the catalytic protocol are necessary for high yields and selectivities providing insight to guide rational optimization of these systems."--Pages v-vi.
The long awaited Handbook for all synthetic chemists working on coupling reactions, compiling all major catalyst components in use in the area. Consists of a compilation of articles taken from the EROS database, with the inclusion of about 20 newly commissioned catalysts/pre-catalysts/ligands that have made an impact in this area of synthetic organic chemistry. Includes catalyst systems used in Heck, Kumada-Tamao-Corriu, Suzuki-Miyaura, Hiyama-Hatanaka, Negishi, Migita-Kosugi-Stille, Buchwald-Hartwig, and Tsuji-Trost coupling reactions.