Zinc catalysis : applications in organic synthesis

Filling the gap in the market for comprehensive coverage of this hot topic, this timely book covers a wide range of organic transformations, e. g. reductions of unsaturated compounds, oxidation reactions, Friedel-Crafts reactions, hydroamination reactions, depolymerizations, transformations of carbo...

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Main Authors Enthaler, Stephan, Wu, Xiao-Feng
Format eBook Book
LanguageEnglish
Published Weinheim Wiley-VCH 2015
Wiley
John Wiley & Sons, Incorporated
Edition1
Subjects
Catalysis
Catalysts
Organic compounds
Organic compounds > Synthesis
Synthesis
TECHNOLOGY & ENGINEERING
Transition metal catalysts
Zinc
Zinc > Industrial applications
Online AccessGet full text
ISBN9783527335985
3527335986
3527675965
9783527675968
DOI10.1002/9783527675944

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Abstract Filling the gap in the market for comprehensive coverage of this hot topic, this timely book covers a wide range of organic transformations, e. g. reductions of unsaturated compounds, oxidation reactions, Friedel-Crafts reactions, hydroamination reactions, depolymerizations, transformations of carbon dioxide, oxidative coupling reactions, as well as C-C, C-N, and C-O bond formation reactions. A chapter on the application of zinc catalysts in total synthesis is also included. With its aim of stimulating further research and discussion in the field, this is a valuable reference for professionals in academia and industry wishing to learn about the latest developments.
AbstractList Filling the gap in the market for comprehensive coverage of this hot topic, this timely book covers a wide range of organic transformations, e. g. reductions of unsaturated compounds, oxidation reactions, Friedel-Crafts reactions, hydroamination reactions, depolymerizations, transformations of carbon dioxide, oxidative coupling reactions, as well as C-C, C-N, and C-O bond formation reactions. A chapter on the application of zinc catalysts in total synthesis is also included. With its aim of stimulating further research and discussion in the field, this is a valuable reference for professionals in academia and industry wishing to learn about the latest developments.
Author Wu, Xiao-Feng
Enthaler, Stephan
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Notes Includes bibliographical references and index
OCLC 903899782
PQID EBC1965991
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Snippet Filling the gap in the market for comprehensive coverage of this hot topic, this timely book covers a wide range of organic transformations, e. g. reductions...
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SubjectTerms Catalysis
Catalysts
Organic compounds
Organic compounds -- Synthesis
Synthesis
TECHNOLOGY & ENGINEERING
Transition metal catalysts
Zinc
Zinc -- Industrial applications
TableOfContents Intro -- Zinc Catalysis -- Contents -- List of Contributors -- Chapter 1 Introduction: Zinc Catalysts for Organic Transformations -- References -- Chapter 2 Zinc-Catalyzed Reductions of Unsaturated Compounds -- 2.1 Introduction -- 2.2 Hydrosilylation of Unsaturated Compounds -- 2.2.1 Nonchiral Hydrosilylation of Carbonyl Bonds -- 2.2.2 Asymmetric Hydrosilylation of C=O Bonds -- 2.2.3 Zinc-Catalyzed Hydrosilylation of C=N and Other Multiple Bonds -- 2.3 Hydrogenation -- 2.4 Transfer Hydrogenation of Unsaturated Compounds -- 2.5 Concluding Remarks -- References -- Chapter 3 Zinc-Catalyzed Oxidation Reactions -- 3.1 Introduction -- 3.2 Oxidative Transformation of Alkenes -- 3.3 Oxidative Transformation of Aldehydes -- 3.4 Oxidative Transformation of C-X Bonds (X=O, N, and S) -- 3.5 Oxidative Functionalization of sp3 C-H Bonds -- 3.6 Other Oxidative Reactions with Redox-Active Ligands -- 3.7 Summary and Outlook -- References -- Chapter 4 Zinc-Catalyzed Friedel-Crafts Reactions -- 4.1 Introduction -- 4.2 Friedel-Crafts Acylation -- 4.3 Friedel-Crafts Alkylations -- 4.3.1 Racemic Friedel-Crafts Alkylation -- 4.3.2 Asymmetric Friedel-Crafts Alkylations -- 4.3.2.1 Friedel-Crafts Alkylations Catalyzed by Chiral Oxazoline/Imidazoline-Zinc(II) Complexes -- 4.3.2.2 Chiral Dinuclear Zinc(II) Complexes as Precatalysts -- 4.3.2.3 Chiral N,N'-Dioxide-Zinc(II) Complexes as Precatalysts -- 4.3.2.4 Chiral (R)-BINAM Based Imine-Zinc(II) Precatalysts -- 4.3.2.5 Chiral Schiff Base-Zinc(II) Complex as Precatalyst -- 4.3.2.6 Chiral Diamines/Thiourea-Zinc(II) Complexes Precatalysts -- 4.3.2.7 Chiral Bipyridine-Zinc(II) Complex as the Precatalyst -- 4.4 Conclusions -- References -- Chapter 5 Zinc-Catalyzed Hydroamination Reactions -- 5.1 Introduction -- 5.2 Inorganic Zinc Salts as Catalysts -- 5.3 Aminotroponiminate Zinc Complexes as Catalysts
5.3.1 Aminotroponiminate Zinc Complex as a Hydroamination Catalyst -- 5.3.2 Modifications of Aminotroponiminate Zinc Complexes -- 5.3.3 Aminotroponiminate Zinc Complex Immobilized on Mesoporous Silica -- 5.4 Other Zinc Organometallic Compounds as Catalysts -- 5.4.1 Other Zn-N Complexes -- 5.4.2 ZnEt2, [Cp*2 Zn2], and [Cp*2Zn] as Hydroamination Precatalysts -- 5.5 Double Metal Cyanide Catalysts -- 5.6 Summary -- References -- Chapter 6 Zinc-Catalyzed C-C Bond Formation -- 6.1 Introduction -- 6.2 Zinc-Catalyzed Aldol-Type Reactions -- 6.2.1 Zinc-Catalyzed Aldol and Mukaiyama-Aldol Reactions -- 6.2.2 Zinc-Catalyzed Michael Addition Reactions -- 6.2.3 Zinc-Catalyzed Henry and Aza-Henry Reactions -- 6.2.4 Zinc-Catalyzed Mannich-Type Reactions -- 6.3 Zinc-Catalyzed Cycloaddition Reactions -- 6.4 Zinc-Catalyzed Addition of Organometallic Reagents to Carbonyl and Related Compounds -- 6.4.1 Alkylation Reactions with Grignard Reagents -- 6.4.2 Allylation, Propargylation, and Allenylation Reactions with Organometallic Reagents -- 6.4.3 Catalytic Acetylide Addition Reactions -- 6.5 Zinc-Catalyzed Cross-Coupling Reactions -- 6.6 Radical Reactions Involving Catalytic Amounts of Zinc -- 6.7 Zinc-Catalyzed Reactions through Alkyne Activation -- 6.8 Zinc-Catalyzed Cyclopropanation Reactions -- 6.9 Other Zinc-Catalyzed Reactions -- 6.10 Summary and Outlook -- References -- Chapter 7 Zinc-Catalyzed C-N and C-O Bond Formation Reactions -- 7.1 Introduction -- 7.2 Zinc-Catalyzed C-N Bond Formation Reactions -- 7.2.1 Zinc-Catalyzed Hydroamination Reactions and Related Processes -- 7.2.1.1 Aminotroponiminate and Related Zinc Complexes as Precatalysts for the Intramolecular Hydroamination of Alkynes and Alkenes -- 7.2.1.2 Metallocene-Based Precatalysts for Inter- and Intramolecular Hydroaminations
7.2.1.3 Diethylzinc and ZnX2 (X=Halogen, OTf) as Precatalysts for Inter- and Intramolecular Hydroaminations -- 7.2.1.4 Zinc-Catalyzed Cascade Reactions Initiated by Inter- and Intramolecular Hydroaminations of Alkenes and Alkynes -- 7.2.2 Zinc-Catalyzed Reactions of Carbonyl Compounds or Carboxylic Acid Derivatives with Amines and Related Compounds -- 7.2.3 Zinc-Catalyzed Reactions Involving Azides and Diazocompounds -- 7.2.4 Zinc-Catalyzed -N-Functionalization of C-H Bonds -- 7.2.5 Zinc-Catalyzed C-N Bond-Forming Reactions Involving the Cleavage of Cyclopropanes and Epoxides -- 7.3 Zinc-Catalyzed C-O Bond Formation Reactions -- 7.3.1 Zinc-Catalyzed C-O Bond Formation Involving Intramolecular Cyclization -- 7.3.2 Zinc-Catalyzed Transesterifications and Amide Cleavages -- 7.3.3 Zinc-Catalyzed Michael Addition/Cyclization Sequence -- 7.3.4 Zinc-Catalyzed Hetero-Diels-Alder Reactions of Aldehydes and Functionalized Dienes -- 7.3.5 Zinc-Catalyzed Multicomponent Reactions -- 7.4 Summary and Conclusion -- References -- Chapter 8 Zinc-Catalyzed Transformation of Carbon Dioxide -- 8.1 Introduction -- 8.2 Zinc Catalysts for the Copolymerization of Epoxides and CO2 -- 8.2.1 Mechanistic Aspects of CO2/Epoxide Copolymerization -- 8.2.2 Heterogeneous Catalysts -- 8.2.3 Homogeneous Catalysts -- 8.2.3.1 Catalyst Development -- 8.2.3.2 Asymmetric Copolymerization -- 8.2.4 Functional Polycarbonates -- 8.3 Zinc-Catalyzed Synthesis of Cyclic Carbonates Utilizing Carbon Dioxide as a Chemical Feedstock -- 8.3.1 Cyclic Carbonates from Cycloaddition of CO2 to Epoxides -- 8.3.1.1 Catalyst Systems and Substrate Scale -- 8.3.1.2 Effect of Reaction Conditions on Cycloaddition Efficiency -- 8.3.1.3 Oxidative Carboxylation -- 8.3.1.4 Reaction Mechanism -- 8.3.2 Cyclization of Carbon Dioxide and Diols -- 8.4 Summary -- References
Chapter 9 Zinc-Catalyzed Depolymerization Reactions -- 9.1 Introduction -- 9.2 Zinc-Catalyzed Depolymerization of Polyethers -- 9.3 Zinc-Catalyzed Depolymerization of Polyesters -- 9.4 Zinc-Catalyzed Depolymerization of Silicones -- 9.5 Summary -- References -- Chapter 10 Applications of Zinc-Promoted Reaction in Total Synthesis -- 10.1 Introduction -- 10.2 Zinc-Promoted Reactions without Ligands -- 10.2.1 Zinc-Catalyzed Reactions -- 10.2.2 Zinc-Mediated Reactions -- 10.3 Zinc-Mediated Reactions with Ligands -- 10.3.1 Zinc-Catalyzed Reactions -- 10.3.2 Zinc-Mediated Reactions -- 10.4 Other Zinc-Promoted Reactions -- References -- Chapter 11 Application of Organozinc Reagents in Oxidative Coupling Reactions -- 11.1 Introduction -- 11.1.1 Oxidative Coupling -- 11.1.2 Organozinc Reagents -- 11.1.3 Preparation of Organozinc Reagents -- 11.1.3.1 Organozinc Halides -- 11.1.3.2 Diorganozincs -- 11.1.3.3 Lithium or Magnesium Zincates -- 11.1.4 Organozinc Halides -- 11.1.4.1 Structures of Organozinc Halides -- 11.1.4.2 Properties of Organozinc Halides -- 11.2 Oxidative Coupling between Zinc Reagents and C(sp) Nucleophiles -- 11.3 Oxidative Coupling between Organozinc Reagents and C(sp2) Nucleophiles -- 11.3.1 C(sp2)-M Compounds as Nucleophiles -- 11.3.2 C(sp2)-H Compounds as Nucleophiles -- 11.4 Oxidative Coupling between Organozinc Reagents and C(sp3) Nucleophiles -- 11.4.1 Oxidative Coupling between Organozinc Reagents and C(sp3)-Organometallic Reagents -- 11.4.2 Oxidative Coupling between Organozinc Reagents and C(sp3)-H Compounds -- 11.5 Oxidative Coupling between Organozinc Reagents and Heteroatom Nucleophiles -- 11.5.1 C-N Bond Formation -- 11.5.2 C-O Bond Formation -- 11.6 Conclusion -- References -- Index -- EULA
Title Zinc catalysis : applications in organic synthesis
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