Application of Transition Metal Catalysts in Organic Synthesis [E-Book] / by L. Brandsma, H. D. Verkruijsse, S. F. Vasilevsky.
Homogeneous catalysis is an important strategy for the synthesis of high-valued chemicals. L. Brandsma has carefully selected and checked the experimental procedures illustrating the catalytic use of copper, nickel, and palladium compounds in organic synthesis. All procedures are on a preparative sc...
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Full text |
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Personal Name(s): | Brandsma, L., author |
Vasilevsky, S. F., author / Verkruijsse, H. D., author | |
Imprint: |
Berlin, Heidelberg :
Springer,
1999
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Physical Description: |
XIX, 335 p. 16 illus. online resource. |
Note: |
englisch |
ISBN: |
9783642603280 |
DOI: |
10.1007/978-3-642-60328-0 |
Series Title: |
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Springer Desktop Editions in Chemistry
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Subject (LOC): |
- 1 Catalysts, Ligands and Reagents
- 1.1 Catalysts
- 1.2 Ligands
- 1.3 Organometallic Reagents
- 2 Procedures for the Preparation of Halogen Compounds
- 2.1 sp-Halides
- 2.2 Aryl and Hetaryl Halides
- 2.3 Olefinic, Cycloolefinic and Allenic Halides
- 3 Cross-Coupling Between 1-Alkynes and 1-Bromoalkynes
- 3.1 Introduction
- Table 1
- 3.2 Scope and Limitations
- 3.3 Relative Reactivities of the Acetylene and the Bromoacetylene
- Table 2
- 3.4 Conditions for the Coupling
- 3.5 Choice of the Reaction Partners
- 3.6 Side Reactions
- 3.7 Experimental Part
- 4 Copper-Catalyzed Aminoalkylation of Acetylenes
- 4.1 Introduction, Scope and Mechanism
- 4.2 Experimental Part
- 5 Copper(I)-Halide-Catalyzed Oxidative Coupling of Acetylenes
- 5.1 Introduction
- 5.2 Methods, Scope and Limitations
- 5.3 About the Mechanism
- 5.4 Experimental Part
- 5.5 Summary of Experimental Conditions for Oxidative Couplings
- Table 3
- 6 Copper(I)-Halide-Catalyzed Substitution of sp2-Halogen by Alkoxide
- 6.1 Introduction
- 6.2 Scope and Limitations of the Copper-Catalyzed Nucleophilic Substitution of sp2-Halogen by Alkoxy Groups
- Table 4
- 6.3 Mechanistic Investigations
- 6.4 Reaction Conditions
- 6.5 Differences in the Reactivities of the Various sp2-Halides
- 6.6 Side Reactions
- 6.7 Applications
- 6.8 Experimental Part
- 7 Copper-Catalyzed Carbon-Carbon Bond Formation by 1,1- and 1,3-Substitution Reactions
- 7.1 Introduction
- 7.2 Displacement of Halide, Tosylate and Acetate in Saturated Compounds
- 7.3 Ring Opening of Saturated Epoxides
- 7.4 Reactions with Allylic Substrates
- 7.5 Reactions with Propargylic and Allenic Substrates
- 7.6 About the Mechanism of Copper Catalyzed Substitutions
- 7.7 Experimental Section
- Table 5
- Table 6
- 8 Nickel Catalyzed Iodo-Dechlorination and Iodo-Debromination of sp2-Halides
- 8.1 Introduction
- 8.2 Scope and Limitations
- 8.3 Mechanistic Investigations
- 8.4 Side Reactions
- 8.5 Experimental Procedures
- 8.6 Conclusions from our Investigations
- 9 Nickel- and Palladium-Catalyzed Cyanation of sp2-Halides and sp2-Triflates
- 9.1 Introduction
- 9.2 Scope and Limitations
- Table 7
- 9.3 Mechanism of the Nickel Catalyzed Cyanation
- 9.4 Methods of Performing Nickel Catalyzed Cyanations
- 9.5 Relative Reactivities of sp2-Halides
- 9.6 Side Reactions
- 9.7 Catalysis by Palladium Compounds
- 9.8 Experimental Part
- 10 Couplings of Acetylenes with sp2-Halides
- 10.1 Introduction
- 10.2 Mechanistic Considerations
- 10.3 Scope and Limitations
- Table 8
- 10.4 Relative Rates of Coupling
- 10.5 Regiochemistry and Stereochemistry
- 10.6 Synthetic Applications of the Cross-Coupling Reactions with Acetylenes
- 10.7 Practical Aspects of the Coupling Reactions
- 10.8 Experimental Section
- 11 Nickel- and Palladium-Catalyzed Cross-Coupling Reactions with Organometallic Intermediates
- 11.1 Introduction
- 11.2 Possibilities of Connecting Organic Groups by Transition Metal Catalysis
- 11.3 Catalysts and Ligands
- 11.4 Leaving Groups
- 11.5 Couplings with Organolithium Compounds
- 11.6 Couplings with Organomagnesium and Organozinc Halides
- 11.7 Cross Couplings with Organoaluminum, Organoboron and Organotin Compounds
- 11.8 Regiochemical and Stereochemical Aspects
- 11.9 Mechanism and Side Reactions
- 11.10 Practical Aspects of Transition-Metal-Catalyzed Couplings
- 11.11 Experimental Section
- Tables 9-20
- Index of Reaction Types
- Index of Experimental Procedures
- Complementary Subject Index.