Innovative Catalysis in Organic Synthesis E-Book
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- Herausgeber: Wiley-VCH
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
C-H, C-O, C-C, and C-Heteroatom bond forming processes by using metal-ligand approaches for the synthesis of organic compounds of
biological, pharmacological and organic nanotechnological utility are the key areas addressed in this book. Authored by a European team
of leaders in the field, it brings together innovative approaches for a variety of catalysis reactions and processes frequently applied in organic
synthesis into a handy reference work. It covers all major types of catalysis, including homogeneous, heterogeneous, and organocatalysis, as
well as mechanistic and computational studies. Special attention is paid to the improvements in efficiency and sustainability of important
catalytic processes, such as selective oxidations, hydrogenation, and cross-coupling reactions, and to their utilization in industry.
The result is a valuable resource for advanced researchers in both academia and industry, as well as graduate students in organic chemistry
aiming for chemo-, regio- or stereoselective synthesis of organic compounds by using novel catalytic systems.
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Seitenzahl: 544
Veröffentlichungsjahr: 2012
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Table of Contents
Related Titles
Title Page
Copyright
Foreword
List of Contributors
Part I: Oxidation Reactions
Chapter 1: Polyoxometalates as Homogeneous Oxidation Catalysts
1.1 Soluble Metal Oxides as Oxidation Catalysts
1.2 Homogeneous Oxidations with POMs Based Only on Mo(VI), W(VI), V(V) Addenda Ions
1.3 Homogeneous Oxidations with TMS-POMs
1.4 Conclusions
Acknowledgments
References
Chapter 2: Bioinspired Oxidations Catalyzed by Nonheme Iron and Manganese Complexes
2.1 Introduction
2.2 Catalytic Oxidation of CC Bonds by Nonheme Iron and Manganese Complexes
2.3 Catalytic Oxidation of C–H Bonds by Nonheme Iron and Manganese Complexes
References
Chapter 3: The Fabulous Destiny of Sulfenic Acids
3.1 Introduction
3.2 Synthesis of Stable Sulfenic Acids
3.3 Generation of Transient Sulfenic Acids
3.4 Reactivity of Sulfenic Acids in the Preparation of Sulfoxides and Unsymmetrical Disulfides
3.5 Synthesis of Stable Sulfenate Anions
3.6 Generation of Transient Sulfenate Anions Leading to Sulfoxides
3.7 Conclusions
References
Chapter 4: Sustainable Catalytic Oxidations with Peroxides
4.1 Introduction
4.2 Metal-Based Selective Oxidations
4.3 Biocatalytic Oxidations with Hydrogen Peroxide
4.4 Conclusions
Acknowledgments
References
Part II: Hydrogenation and Reduction Reactions
Chapter 5: Asymmetric Hydrogenation of Dehydroamino acid Derivatives by Rh-Catalysts with Chiral Monodentate P-Ligands
5.1 Introduction
5.2 Chiral Monodentate Phosphorus Ligands in Asymmetric Hydrogenation
5.3 Catalyst Precursors
5.4 Mechanistic Insights
5.5 Formation of the MAC Adducts
5.6 Evolution of MAC-Adducts and Origin of Enantioselection
References
Chapter 6: Recent Advances in the Synthesis and Catalytic Hydrogenation of Dehydroamino Acid Derivatives and Bicyclo[2.2.2]octenes
6.1 Introduction
6.2 Synthesis of DDAA Derivatives and Bicyclo[2.2.2]octenes
6.3 Ligands
6.4 Homogeneous Hydrogenation and Hydrogenolysis Reactions with Dehydroamino Acid Derivatives and Bicyclo[2.2.2]oct-7-enes over Nanocolloids-Modified Catalysts
6.5 Heterogeneous Catalysts for Hydrogenolysis of Bicyclo[2.2.2]oct-7-enes
6.6 Layered-Double Hydroxides as a Support for Rh(TPPTS)3 and Rh-(m-TPPTC)3 Homogeneous Catalysts
6.7 Conclusions
Acknowledgments
References
Chapter 7: Ir-Catalyzed Hydrogenation of Minimally Functionalized Olefins Using Phosphite–Nitrogen Ligands
7.1 Introduction
7.2 Application of Phosphite–Nitrogen Ligands
7.3 Conclusions
Acknowledgments
References
Chapter 8: Modeling in Homogeneous Catalysis: a Tutorial
8.1 Introduction
8.2 Molecular Modeling
8.3 Wave Function Theory, WFT
8.4 Density Functional Theory, DFT
8.5 Orbitals
8.6 Basis Sets
8.7 Solvation
8.8 Analyzing the Reaction Energies
8.9 Analyzing the Electronic Structure
References
Part III: C–C and C–Hetero Bond-Forming Reactions
Chapter 9: Golden Times for Allenes
9.1 Introduction
9.2 Cyclization of Hydroxyallenes
9.3 Cyclization of Aminoallenes
9.4 Cyclization of Thioallenes
9.5 Conclusion
References
Chapter 10: Copper Catalysis in Arene and Heteroarene Functionalization through C–H Bond Activation
10.1 Introduction
10.2 C–C Bond-Forming Reactions
10.3 C–N Bond-Forming Reactions
10.4 C–O Bond-Forming Reactions
10.5 C–Halogen Bond-Forming Reactions
References
Chapter 11: Ligated Organocuprates: An A–Z Routemap of Mechanism and Application
11.1 Introduction
11.2 Accepted Mechanistic Proposals
11.3 Selective Applications in Privileged Copper(I) Catalysis
References
Chapter 12: Rh-, Ag-, and Cu-Catalyzed C–N Bond Formation
12.1 Introduction
12.2 Historical Background
12.3 Copper- and Silver-Catalyzed C–N Bond Formation
12.4 Rhodium-Catalyzed C–N Bond Formation
12.5 Conclusions
References
Chapter 13: Development of the Asymmetric Nozaki–Hiyama–Kishi Reaction
13.1 Introduction
13.2 Development of a Catalytic Nozaki–Hiyama–Kishi Reaction
13.3 Catalytic Enantioselective Nozaki–Hiyama–Kishi Reaction
13.4 Application of Salen-Derived Ligands in the Enantioselective Nozaki–Hiyama–Kishi Reaction
13.5 Application of Oxazoline-Containing Ligands in the Catalytic Enantioselective Nozaki–Hiyama–Kishi Reaction
13.6 Application of Tethered Bis(8-quinolinato) Chromium Complexes in the Catalytic Enantioselective Nozaki–Hiyama–Kishi
13.7 Application of Chiral Spirocyclic Borate Ligands to the Catalytic Enantioselective Nozaki–Hiyama–Kishi Allylation
13.8 Applications of Catalytic Nozaki–Hiyama–Kishi Reaction in Total Synthesis
13.9 Conclusions
References
Chapter 14: Chiral Imidate Ligands: Synthesis and Applications in Asymmetric Catalysis
14.1 Introduction
14.2 Cyclic Imidates
14.3 Synthesis of Imidates
14.4 Synthesis of Imidate Ligands
14.5 Synthesis of Imidate–Copper (I) Complexes
14.6 Application of Chiral Imidate Ligands in Enantioselective Catalysis
14.7 Novel Synthetic Applications of Cyclic Imidates
14.8 Conclusions
References
Chapter 15: Catalyzed Organic Reactions in Ball Mills
15.1 Introduction
15.2 Acid- or Base-Catalyzed Reactions
15.3 Organocatalytic Methods
15.4 Metal-Catalyzed Reactions
15.5 Conclusion and Perspective
References
Index
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Catalytic Asymmetric Synthesis
The Editor
Prof. Dr. Pher G. Andersson
Uppsala University
Department of Biochemistry and
Organic Chemistry
Husargatan 3
751 23 Uppsala
Sweden
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Foreword
This book had its genesis at a meeting on European Cooperation in Science and Technology (COST) in Ankara, Turkey, in 2010. The Actions of COST not only promote the development of new and exciting science but they are also a marvellous mechanism for bringing together new alliances and friendships between disparate communities of scientists where the sum is most definitely worth more than the separate paths. When Pher Andersson volunteered to coordinate a book describing some of the highlights of the endeavours of our own Action (D40) — “Innovative Catalysis: New Processes and Selectivities” I and others were wildly supportive. Not only did it seem an appropriate way to mark the end of five years of previous collaboration between laboratories in 23 separate countries, but the time is ripe to define what is new and exciting in the, now mature, field of selective catalysis. The experts of D40 have come together to give their own personal take on what they consider to be “innovative” approaches to catalysis in this first decade of the twenty-first century. I am most grateful to them all for freely volunteering their time and especially to Pher Andersson for bringing this mission to a speedy conclusion. I am sure that you will find something to pique your imagination for your own research in the next decade within — enjoy!
Simon Woodward
Chair, COST Action D40 (2007–2011)
ESF provides the COST Office through an EC contract
COST is supported by the EU RTD Framework programme
COST—the acronym for European Cooperation in Science and Technology— is the oldest and widest European intergovernmental network for cooperation in research. Established by the Ministerial Conference in November 1971, COST is presently used by the scientific communities of 36 European countries to cooperate in common research projects supported by national funds.
The funds provided by COST — less than 1% of the total value of the projects — support the COST cooperation networks (COST Actions) through which, with EUR 30 million per year, more than 30 000 European scientists are involved in research having a total value that exceeds EUR 2 billion per year. This is the financial worth of the European added value, which COST achieves.
A “bottom-up approach” (the initiative of launching a COST Action comes from the European scientists themselves), “à la carte participation” (only countries interested in the Action participate), “equality of access” (participation is open also to the scientific communities of countries not belonging to the European Union) and “flexible structure” (easy implementation and light management of the research initiatives) are the main characteristics of COST. As precursor of advanced multidisciplinary research COST has a very important role for the realisation of the European Research Area (ERA) anticipating and complementing the activities of the Framework Programmes, constituting a “bridge” toward the scientific communities of emerging countries, increasing the mobility of researchers across Europe and fostering the establishment of “Networks of Excellence” in many key scientific domains such as Biomedicine and Molecular Biosciences; Food and Agriculture; Forests, their Products and Services; Materials, Physical and Nanosciences; Chemistry and Molecular Sciences and Technologies; Earth System Science and Environmental Management; Information and Communication Technologies; Transport and Urban Development; and Individuals, Societies, Cultures, and Health. It covers basic and more applied research and also addresses issues of pre-normative nature or societal importance.
Web: http://www.cost.eu
List of Contributors
Part I
Oxidation Reactions
Chapter 1
Polyoxometalates as Homogeneous Oxidation Catalysts
Mauro Carraro, Andrea Sartorel, Masooma Ibrahim, Nadeen Nsouli, Claire Jahier, Sylvain Nlate, Ulrich Kortz, and Marcella Bonchio
1.1 Soluble Metal Oxides as Oxidation Catalysts
Polyoxometalates (POMs) are discrete multitransition metal oxides characterized by a formidable structural variety, resulting in different dimensions, shape, charge density, surface reactivity, and in a rich redox chemistry [1–7]. A first classification of POMs is based on the chemical composition of these species, essentially represented by two types of general formula [8]:
where M is the main transition metal constituent of the POM, O is the oxygen atom, and X can be a nonmetal of the p block or a different transition metal.
Owing to their particular composition and electronic structure, POMs can be considered as discrete models of extended metal oxides. As for the latters, the doping process is a winning strategy to improve their catalytic behavior. Even if there are several examples concerning electrostatic interaction with different transition metal cations, the most stable coordination mode is on incorporation of the transition metal in the POM structure with the formation of ().
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