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The Resource Application of Transition Metal Catalysts in Organic Synthesis, by L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse, (electronic resource)

Application of Transition Metal Catalysts in Organic Synthesis, by L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse, (electronic resource)

Creator
Author
Contributor
Summary
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 scale, make economic use of solvents and catalysts, avoid toxic substances and have high yields
Language
  • eng
  • eng
Work
Publication
Edition
1st ed. 1999.
Extent
1 online resource (XIX, 335 p. 16 illus.)
Note
Bibliographic Level Mode of Issuance: Monograph
Contents
  • 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
Isbn
9783642603280
Instance
Label
Application of Transition Metal Catalysts in Organic Synthesis
Title
Application of Transition Metal Catalysts in Organic Synthesis
Statement of responsibility
by L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse
Creator
Contributor
Author
Author
Subject
Language
  • eng
  • eng
Summary
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 scale, make economic use of solvents and catalysts, avoid toxic substances and have high yields
Member of
http://library.link/vocab/creatorName
Brandsma, L
Dewey number
547/.2
http://bibfra.me/vocab/relation/httpidlocgovvocabularyrelatorsaut
  • OxRtPpCAaCg
  • lyicFMbDs1o
  • PXraXGj3dGw
Image bit depth
0
Language note
English
LC call number
QD415-436
Literary form
non fiction
Nature of contents
dictionaries
http://library.link/vocab/relatedWorkOrContributorName
  • Vasilevsky, S.F.
  • Verkruijsse, H.D.
Series statement
Springer Desktop Editions in Chemistry
http://library.link/vocab/subjectName
  • Chemistry, Organic
  • Chemistry, Physical organic
  • Chemistry, inorganic
  • Organic Chemistry
  • Physical Chemistry
  • Inorganic Chemistry
Label
Application of Transition Metal Catalysts in Organic Synthesis, by L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse, (electronic resource)
Instantiates
Publication
Note
Bibliographic Level Mode of Issuance: Monograph
Antecedent source
mixed
Bibliography note
Includes bibliographical references at the end of each chapters and indexes
Carrier category
online resource
Carrier category code
  • cr
Color
not applicable
Content category
text
Content type code
  • txt
Contents
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
Dimensions
unknown
Edition
1st ed. 1999.
Extent
1 online resource (XIX, 335 p. 16 illus.)
File format
multiple file formats
Form of item
online
Isbn
9783642603280
Level of compression
uncompressed
Media category
computer
Media type code
  • c
Other control number
10.1007/978-3-642-60328-0
Quality assurance targets
absent
Reformatting quality
access
Specific material designation
remote
System control number
  • (CKB)3400000000104967
  • (SSID)ssj0000805150
  • (PQKBManifestationID)11425177
  • (PQKBTitleCode)TC0000805150
  • (PQKBWorkID)10835443
  • (PQKB)11450589
  • (DE-He213)978-3-642-60328-0
  • (MiAaPQ)EBC3092713
  • (EXLCZ)993400000000104967
Label
Application of Transition Metal Catalysts in Organic Synthesis, by L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse, (electronic resource)
Publication
Note
Bibliographic Level Mode of Issuance: Monograph
Antecedent source
mixed
Bibliography note
Includes bibliographical references at the end of each chapters and indexes
Carrier category
online resource
Carrier category code
  • cr
Color
not applicable
Content category
text
Content type code
  • txt
Contents
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
Dimensions
unknown
Edition
1st ed. 1999.
Extent
1 online resource (XIX, 335 p. 16 illus.)
File format
multiple file formats
Form of item
online
Isbn
9783642603280
Level of compression
uncompressed
Media category
computer
Media type code
  • c
Other control number
10.1007/978-3-642-60328-0
Quality assurance targets
absent
Reformatting quality
access
Specific material designation
remote
System control number
  • (CKB)3400000000104967
  • (SSID)ssj0000805150
  • (PQKBManifestationID)11425177
  • (PQKBTitleCode)TC0000805150
  • (PQKBWorkID)10835443
  • (PQKB)11450589
  • (DE-He213)978-3-642-60328-0
  • (MiAaPQ)EBC3092713
  • (EXLCZ)993400000000104967

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