
Zinc Catalysis : Applications in Organic Synthesis.
Title:
Zinc Catalysis : Applications in Organic Synthesis.
Author:
Enthaler, Stephan.
ISBN:
9783527675975
Personal Author:
Edition:
1st ed.
Physical Description:
1 online resource (326 pages)
Contents:
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.
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.
Local Note:
Electronic reproduction. Ann Arbor, Michigan : ProQuest Ebook Central, 2017. Available via World Wide Web. Access may be limited to ProQuest Ebook Central affiliated libraries.
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