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Chiral titanium complexes are low-cost, low-toxicity and high-efficiency catalysts. Impressive progress on enantioselective titanium-catalysed transformations has been achieved in the past seven years, with exciting new discoveries ranging from basic reactions to novel methodologies. Despite this, the field has not been substantially reviewed since 2008.This book contains up to date research and covers all types of enantioselective transformations using chiral titanium catalysts. It illustrates the economic, health, and environmental benefits of chiral titanium catalysts, showing the types of highly enantioselective reactions that they are able to induce are unlimited.Work presented here is aimed at researchers in organic and catalytic chemistry, and has been carefully curated to encourage future research possibilities.
Developments of new catalytic transformations by using earth-abundant metal (base-metal) catalysts have played a significant role in modern civilization and will continue to play a vital role towards maintaining and improving our quality of life. Particularly, these transformations have had a tremendous impacts on the agricultural, transport, energy, and pharmaceutical sectors. This field of base-metal catalysis would enjoy added benefits with the utilization of sustainable feedstock carbon sources for fine chemical synthesis. However, the dual problems of activation of thermodynamically stable precursors (ethylene, CO2, H2, CO, aldehydes, acrylates, HCN) and their highly stereoselective incorporation into other readily available substrates (1,3-dienes, alkynes, enynes) pose new challenges. In a nutshell, the development of benign catalysts for employing sustainable feedstock starting materials has the potential to transform inexpensive materials into valuable precursors for fine chemical synthesis. My dissertation work focuses on the development of scalable, atom-economical, and cost-effective catalytic methods for the preparation of value-added products relevant to fine chemicals. The overarching aims are to use sustainable feedstocks or readily available precursors, and environmentally benign chemistry. To achieve these goals, three efficient catalytic methods have been developed which employ complexes of an earth-abundant metal, cobalt, with ligands derived from naturally occurring amino acids or commercially available bis-phosphine ligands. The key to success was a systematic ligands investigation that inspired the design and synthesis of novel ligands to achieve high chemo-, regio-, and enantioselectivities. In the first methodology, a broadly applicable method affecting [2+2] cycloaddition between several alkynes and alkenyl derivatives to form cyclobutenes has been disclosed. A library of >70 nearly enantiopure cyclobutenes, which are ubiquitous motifs in bioactive compounds, have been synthesized in excellent yields. In the second methodology, ligand controlled regio-divergent enantioselective synthesis of primary and secondary homoallylic boronates (>50 examples) from readily available 1,3-dienes and a common boron reagent have been developed. Furthermore, the hydrofunctionalization of 1,3-dienes program has been extended to unprecedented enantioselective hydroacylation of 1,3-dienes. This method opens a realm to achieve the synthesis of enantiopure alpha- or beta-chiral center containing ketones. In all the mentioned transformations above, cationic Co(I)- species has been invoked as an active catalyst. To further corroborate the role of cationic Co(I)-complexes, a reliable protocol has been developed to synthesize, isolate discrete neutral and cationic Co(I)-complexes and characterized by X-ray crystallography. These isolated cationic complexes serve as an excellent single-component catalyst for heterodimerization, hydroboration, and hydroacylation, suggesting the key role of cationic Co(I)-complexes in these transformations. While developing these efficient methodologies, striking ligand, counterion, and solvent effects have been revealed along with a unique role of a cationic Co(I) intermediate in the reactions which advanced novel fundamental concepts. We believe that these cationic Co(I) complexes have broader utility in homogeneous catalysis. We hope that the rational evolution of a mechanism-based strategy that led to the eventual successful outcome and the attendant support studies will add to the burgeoning organometallic chemistry of cobalt and its applications with further implications beyond the synthetic reactions described in this dissertation.
In this reference leaders at the forefront of research provide an insight into one of the hottest topics in organic synthesis, focusing on the most important enantioselective reactions. Clearly structured, each entry begins with a concise introduction, including a mechanistic discussion of the reaction, followed by preparative guidelines for newcomers, such as carefully selected working procedures with critical notes for bench chemists, rules of thumb and tips and tricks.
Provides a much-needed account of the formidable "cobalt rush" in organic synthesis and catalysis Over the past few decades, cobalt has turned into one of the most promising metals for use in catalytic reactions, with important applications in the efficient and selective synthesis of natural products, pharmaceuticals, and new materials. Cobalt Catalysis in Organic Synthesis: Methods and Reactions provides a unique overview of cobalt-catalysed and -mediated reactions applied in modern organic synthesis. It covers a broad range of homogeneous reactions, like cobalt-catalysed hydrogenation, hydrofunctionalization, cycloaddition reactions, C-H functionalization, as well as radical and biomimetic reactions. First comprehensive book on this rapidly evolving research area Covers a broad range of homogeneous reactions, such as C-H activation, cross-coupling, synthesis of heterocyclic compounds (Pauson-Khand), and more Chapters on low-valent cobalt complexes as catalysts in coupling reactions, and enantioselective cobalt-catalyzed transformations are also included Can be used as a supplementary reader in courses of advanced organic synthesis and organometallic chemistry Cobalt Catalysis in Organic Synthesis is an ideal book for graduates and researchers in academia and industry working in the field of synthetic organic chemistry, catalysis, organometallic chemistry, and natural product synthesis.
Catalytic Asymmetric Synthesis Seminal text presenting detailed accounts of the most important catalytic asymmetric reactions known today This book covers the preparation of enantiomerically pure or enriched chemical compounds by use of chiral catalyst molecules. While reviewing the most important catalytic methods for asymmetric organic synthesis, this book highlights the most important and recent developments in catalytic asymmetric synthesis. Edited by two well-qualified experts, sample topics covered in the work include: Metal catalysis, organocatalysis, photoredox catalysis, enzyme catalysis C–H bond functionalization reactions Carbon–carbon bond formation reactions, carbon–halogen bond formation reactions, hydrogenations, polymerizations, flow reactions Axially chiral compounds Retaining the best of its predecessors but now thoroughly up to date with the important and recent developments in catalytic asymmetric synthesis, the 4th edition of Catalytic Asymmetric Synthesis serves as an excellent desktop reference and text for researchers and students, from upper-level undergraduates all the way to experienced professionals in industry or academia.
Since the turn of the last century when the field of catalysis was born, iron and cobalt have been key players in numerous catalysis processes. These metals, due to their ability to activate CO and CH, haev a major economic impact worldwide. Several industrial processes and synthetic routes use these metals: biomass-to-liquids (BTL), coal-to-liquids (CTL), natural gas-to-liquids (GTL), water-gas-shift, alcohol synthesis, alcohol steam reforming, polymerization processes, cross-coupling reactions, and photocatalyst activated reactions. A vast number of materials are produced from these processes, including oil, lubricants, waxes, diesel and jet fuels, hydrogen (e.g., fuel cell applications), gasoline, rubbers, plastics, alcohols, pharmaceuticals, agrochemicals, feed-stock chemicals, and other alternative materials. However, given the true complexities of the variables involved in these processes, many key mechanistic issues are still not fully defined or understood. This Special Issue of Catalysis will be a collaborative effort to combine current catalysis research on these metals from experimental and theoretical perspectives on both heterogeneous and homogeneous catalysts. We welcome contributions from the catalysis community on catalyst characterization, kinetics, reaction mechanism, reactor development, theoretical modeling, and surface science.
This book meets the long-felt need for a reference on ferrocenes with the focus on catalysis. It provides a thorough overview of the synthesis and characterization of different types of chiral ferrocene ligands, their application to various catalytic asymmetric reactions, and versatile chiral materials as well as drug intermediates synthesized from them. Written by the "who's who" of ferrocene catalysis, this is a guide to the design of new ferrocene ligands and synthesis of chiral synthetic intermediates, and will thus be useful for organic, catalytic and synthetic chemists working in academia, industrial research or process development.
The series Topics in Current Chemistry Collections presents critical reviews from the journal Topics in Current Chemistry organized in topical volumes. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience.Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field.The chapter "Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates" is available open access under a CC BY 4.0 License via link.springer.com.