Modern alkyne chemistry : catalytic and atom-economic transformations / edited by Barry M. Trost and Chao-Jun Li ; contributors, Kenneth Avocetien [and twenty-four others].

Format:

Book

Contributor:

Trost, Barry M., editor.

Li, Chao-Jun, editor.

Avocetien, Kenneth, contributor.

Language:

English

Subjects (All):

Chemistry, Technical.

Chemistry.

Organic compounds--Synthesis.

Organic compounds.

Physical Description:

1 online resource (423 p.)

Edition:

1st ed.

Place of Publication:

Weinheim, Germany : Wiley-VCH, 2015.

Language Note:

English

Summary:

A comprehensive and up-to-date overview of alkyne chemistry, taking into account the progress made over the last two decades. The experienced editors are renowned world leaders in the field, while the list of contributors reads like a ""Who''s Who"" of synthetic organic chemistry.<br>The result is a valuable reference not only for organic chemists at universities and in the chemical industry, but also for biologists and material scientists involved in the modern synthesis of organic compounds and materials.<br>

Contents:

Modern Alkyne Chemistry; Contents; List of Contributors; Preface; Chapter 1 Introduction; 1.1 History of Alkynes; 1.2 Structure and Properties of Alkynes; 1.3 Classical Reactions of Alkynes; 1.4 Modern Reactions; 1.5 Conclusion; References; Part I Catalytic Isomerization of Alkynes; Chapter 2 Redox Isomerization of Propargyl Alcohols to Enones; 2.1 Introduction; 2.2 Base Catalysis; 2.3 Ru Catalyzed; 2.4 Rh Catalysis; 2.5 Palladium Catalysis; 2.6 Miscellaneous; 2.7 Conclusions; References; Chapter 3 Carbophilic Cycloisomerization Reactions of Enynes and Domino Processes

3.1 Introduction and Reactivity Principles3.1.1 The Reactivity of Carbophilic Lewis Acids in the Presence of Enyne Substrates; 3.2 Skeletal Rearrangement Reactions in the Absence of Nucleophiles; 3.2.1 Synthesis of Dienes (1,3- and 1,4-Dienes); 3.2.2 Cycloisomerization Reactions Involving Activated Alkene Partners: Conia-Ene Reaction and Related Transformations; 3.2.3 Formation of Bicyclic Derivatives; 3.2.3.1 Formation of Bicyclopropanes; 3.2.3.2 Formation of Bicyclobutenes; 3.2.3.3 Formation of Larger Rings via Cycloisomerization-Rearrangements; 3.3 Enyne Domino Processes

3.3.1 Domino Enyne Cycloisomerization-Nucleophile Addition Reactions3.3.1.1 Oxygen and Nitrogen Nucleophiles; 3.3.1.2 Carbon Nucleophiles; 3.4 Conclusion; References; Chapter 4 Alkyne Metathesis in Organic Synthesis; 4.1 Introduction; 4.2 Mechanistic Background and Classical Catalyst Systems; 4.3 State-of-the-Art Catalysts; 4.4 Basic Reaction Formats and Substrate Scope; 4.5 Selected Applications; 4.5.1 Dehydrohomoancepsenolide; 4.5.2 Olfactory Macrolides; 4.5.3 Haliclonacyclamine C; 4.5.4 Hybridalactone; 4.5.5 Cruentaren A; 4.5.6 The Tubulin-Inhibitor WF-1360F; 4.5.7 Neurymenolide A

4.5.8 Leiodermatolide4.5.9 Tulearin C; 4.5.10 The Antibiotic A26771B; 4.5.11 Lactimidomycin; 4.5.12 Citreofuran; 4.5.13 Polycavernoside; 4.5.14 Amphidinolide F; 4.5.15 Spirastrellolide F Methyl Ester; 4.6 Conclusions; References; Part II Catalytic Cycloaddition Reactions; Chapter 5 Alkyne-Azide Reactions; 5.1 Introduction; 5.2 Reviews on Cu-Catalyzed Azide-Alkyne Cycloaddition; 5.3 Mechanistic Considerations on the Cu(1) Catalysis; 5.4 The Substrates for CuAAC; 5.5 The Environment; 5.6 Modified 1,2,3-Triazoles and CuAAC Side Reactions; 5.6.1 Oxidative Couplings of Cu(1)-Triazole Complexes

5.6.2 Reactions in the 5-Position of Triazoles5.6.3 Side Reactions due to Substrate Instability; 5.7 The Catalyst; 5.7.1 Recent Ligands and their Influence on Cu(1) Catalysis; 5.7.2 Catalyst Structure-Activity Relationship; 5.7.3 In Situ Generated CuAAC: Electro-, Photo-, and Self-Induced ``Click''''; 5.8 Optimizing Conditions for CuAAC Reactions; 5.9 CuAAC in Biological Applications; 5.10 Biocompatibility of the CuAAC Reaction; References; Chapter 6 Catalytic Cycloaddition Reactions; 6.1 Introduction; 6.2 (2+2) Cycloaddition; 6.3 (3+2) and (2+1) Cycloaddition; 6.4 (4+2) Cycloaddition

6.5 (5+1) and (4+1) Cycloadditions

Notes:

Description based upon print version of record.

Includes bibliographical references at the end of each chapters and index.

Description based on online resource; title from PDF title page (ebrary, viewed October 24, 2014).

ISBN:

9783527677900

3527677909

9783527677894

3527677895

9783527677917

3527677917

OCLC:

893333080