Modern Gold Catalyzed Synthesis E-Book

• Herausgeber: Wiley-VCH
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 602

Veröffentlichungsjahr: 2012

Beschreibung

With its impressive features, gold has led to completely new reaction types in recent years, which in turn have strongly influenced both
organic catalysis and material science. Other fields where a significant amount of new results has been obtained include nanotechnology,
self assembly/supramolecular systems and biochemical/medicinal chemistry. As a result, gold is one of the hottest topics in catalysis at
the moment, with an increasing amount of research being carried out in this field.
While focusing on homogeneous catalysis, this monograph also covers the main applications in heterogeneous catalysis. Following
a look at the gold-catalyzed addition of heteroatom nucleophiles to alkynes, it goes on to discuss gold-catalyzed additions to allenes and
alkenes, gold-catalyzed benzannulations, cycloisomerization and rearrangement reactions, as well as oxidation and reduction reactions.
The whole is finished off with a section on gold-catalyzed aldol and related reactions and the application of gold-catalyzed reactions to natural
product synthesis.
Of interest to synthetic chemists and inorganic chemists, as well as organic chemists working in homogeneous catalysis, physical and
technical chemists.

Leseprobe

Contents

Cover

Further Reading

Title Page

Copyright

List of Contributers

Chapter 1: Hydrochlorination of Acetylene Catalyzed by Gold

1.1 Introduction

1.2 Reactions of Alkynes Using Gold Chloride as Catalyst

1.3 The Correlation of E° with the Activity of Gold for the Hydrochlorination of Acetylene

1.4 Central Role of Au3+ and Regeneration of Au/C Catalysts

1.5 Reaction Mechanism of Alkynes Over Au/C Catalysts

1.6 Chemical Origin of the E° Correlation and General Remarks

1.7 Commercial Processes and Economic Aspects of Vinyl Chloride Monomer Manufacture

References

Chapter 2: Gold-Catalyzed Reduction Reactions

2.1 Introduction

2.2 Hydrogenation of Multiple C=C Bonds. Role of the Gold Oxidation State

2.3 Hydrogenation of α,β-Unsaturated Aldehydes

2.4 Hydrogenation of Substituted Nitroaromatic Compounds

References

Chapter 3: Gold-Catalyzed Benzannulations: Asao–Yamamoto Benzopyrylium Pathway

3.1 Introduction

3.2 Acetylenic Compounds as 2π Systems

3.3 Enols as 2π Systems

3.4 Enol Ethers as 2π Systems

3.5 Benzynes as 2π Systems

3.6 Synthesis of Phthalazine Derivatives

3.7 Application to the Synthesis of Angucyclinone Antibiotics and Other Applications in Total Synthesis

3.8 Copper-Catalyzed Benzannulations

3.9 Conclusion

References

Chapter 4: Gold-Catalyzed Reactions of Propargyl Esters, Propargyl Alcohols, and Related Compounds

4.1 Introduction and Extent of This Chapter

4.2 Propargyl Esters

4.3 Propargyl Ethers

4.4 Propargyl Alcohols

4.5 Propargyl Amines

4.6 Propargyl Carbonates, Amides, and Carbamates

4.7 Other Propargyl Substitution Patterns

4.8 Conclusion

Reagent Abbreviations

References

Chapter 5: Intramolecular Hydroarylation of Alkynes

5.1 Introduction

5.2 Intramolecular Reactions of Arenes with Alkynes

5.3 Intramolecular Reactions of Electron-Rich Heteroarenes with Alkynes

5.4 Conclusion and Outlook

Acknowledgments

References

Chapter 6: Gold–Alkyne Complexes

6.1 Introduction

6.2 Description of the M–π-Bond Interaction in Alkene and Alkyne Complexes

6.3 Gold(0) Complexes

6.4 Gold(I) Complexes

6.5 Gold(III) complexes

6.6 Theoretical Studies

References

Chapter 7: Gold–Alkene Complexes

7.1 Introduction

7.2 Gold(0) Derivatives

7.3 Gold(I) Complexes

7.4 Gold(III) Complexes

7.5 Theoretical Studies

References

Chapter 8: Hydration and Hydroalkoxylation of CC Multiple Bonds

8.1 Historical Perspective

8.2 Gold Catalysts

8.3 Hydration and Hydroalkoxylation of CC Triple Bonds (Alkynes)

8.4 Hydration and Hydroalkoxylation of CC Double Bonds (Allenes and Alkenes)

References

Chapter 9: Gold-Catalyzed Aldol and Related Reactions

9.1 The Gold-Catalyzed Aldol Reaction

9.2 Related Reactions

Acknowledgement

References

Chapter 10: Gold-Catalyzed Oxidation Reactions: Oxidation of Alkenes

10.1 Introduction

10.2 Epoxidation Reactions

10.3 Aziridination Reactions

10.4 Oxidative Cleavage of C=C Double Bonds

10.5 Oxygen Transfer to Carbenoids

References

Chapter 11: Gold-Catalyzed Oxygen-Atom Transfer to Alkynes

11.1 Introduction

11.2 Oxygen-Atom Transfer from NO Groups

11.3 Oxygen-Atom Transfer from Sulfoxides

11.4 Oxygen-Atom Transfer from Epoxides

11.5 Gold-Catalyzed Oxidative Coupling

References

Chapter 12: Gold-Catalyzed Additions to Alkenes: N-Nucleophiles

References

Chapter 13: Gold-Catalyzed Additions to Alkenes: O-Nucleophiles

References

Chapter 14: Oxidation of Alcohols and Carbohydrates

14.1 Introduction

14.2 Selective Oxidation of Alcohols

14.3 Selective Oxidation of Carbohydrates

14.4 Future Applications

14.5 Conclusion

References

Chapter 15: Applications of Gold-Catalyzed Reactions to Natural Product Synthesis

15.1 Introduction

15.2 Addition of Heteroatom Nucleophiles to Alkynes

15.3 Addition of Heteroatom Nucleophiles to Allenes

15.4 Cycloadditions via Pyrylium Intermediates from o-Alkynylacylarenes

15.5 Rearrangements of Propargyl Esters

15.6 Skeletal Rearrangement of 3-Butynyl-N-Oxides: (±)-Cermizine and (+)-Lentiginosine

15.7 Enyne Cyclizations

15.8 Propargyl Claisen Rearrangement: Azadirachtin

15.9 Gold-Catalyzed C–H Activation: (±)-Pterocarpan and Crassifolone

15.10 Gold-Catalyzed Allylic Amination: (±)-Angustureine

15.11 Catalytic Asymmetric Aldol Reaction of Isocyanoacetates and Aldehydes

References

Chapter 16: Gold-Catalyzed Addition Reactions to Allenes

16.1 Introduction

16.2 Addition of Heteroatom Nucleophiles

16.3 Addition of Carbon Nucleophiles

16.4 Conclusion

References

Index

Further Reading

Mohr, F. (ed.)

Gold Chemistry

Highlights and Future Directions

2009

ISBN: 978-3-527-32086-8

Laguna, A. (ed.)

Modern Supramolecular Gold Chemistry

Gold-Metal Interactions and Applications

2008

ISBN: 978-3-527-32029-5

Dupont, J., Pfeffer, M. (eds.)

Palladacycles

Synthesis, Characterization and Applications

2008

ISBN: 978-3-527-31781-3

Ertl, G., Knözinger, H., Schüth, F.,

Weitkamp, J. (eds.)

Handbook of Heterogeneous Catalysis

8 Volumes

2008

ISBN: 978-3-527-31241-2

Ding, K., Uozumi, Y. (eds.)

Handbook of Asymmetric Heterogeneous Catalysis

2008

ISBN: 978-3-527-31913-8

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Print ISBN: 978-3-527-31952-7

ePDF ISBN: 978-3-527-64689-0

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Cover Design Formgeber, Eppelheim

Typesetting Thomson Digital, Noida, India

List of Contributors

Naoki Asao

Tohoku University

Graduate School of Science

Department of Chemistry

Sendai 980-8578

Japan

Maria Camila Blanco Jaimes

Universität Heidelberg

Organisch-Chemisches Institut

Im Neuenheimer Feld 270

69120 Heidelberg

Germany

David A. Capretto

University of Chicago

Department of Chemistry

5735 South Ellis Avenue

Chicago

IL 60635

USA

Maria Agostina Cinellu

Università di Sassari

Dipartimento di Chimica

Via Vienna 2

07100 Sassari

Italy

Marco Conte

Cardiff University

School of Chemistry

Cardiff Catalysis Institute

Cardiff CF10 3AT

UK

Avelino Corma

Universidad Politécnica de Valencia

Instituto de Tecnología Química

Avenida de los Naranjos s/n

46022 Valencia

Spain

Cristina Della Pina

Università degli Studi di Milano

Dipartimento di Chimica Inorganica, Metallorganica e Analitica

Via Venezian 21

20133 Milan

Italy

Paula de Mendoza

Institute of Chemical Research of Catalonia (ICIQ)

Avinguda Països Catalans 16

43007 Tarragona

Spain

Antonio M. Echavarren

Institute of Chemical Research of Catalonia (ICIQ)

Avinguda Països Catalans 16

43007 Tarragona

and

Universitat Rovira i Virgili

Departament de Química Analítica i Química Orgà nica

c/ Marcel·li Domingo s/n

43007 Tarragona

Spain

Ermelinda Falletta

Università degli Studi di Milano

Dipartimento di Chimica Inorganica, Metallorganica e Analitica

Via Venezian 21

20133 Milan

Italy

A. Stephen K. Hashmi

Universität Heidelberg

Organisch-Chemisches Institut

Im Neuenheimer Feld 270

69120 Heidelberg

Germany

Chuan He

University of Chicago

Department of Chemistry

5735 South Ellis Avenue

Chicago

IL 60635

USA

Christoph Hubbert

Universität Heidelberg

Organisch-Chemisches Institut

Im Neuenheimer Feld 270

69120 Heidelberg

Germany

Graham J. Hutchings

Cardiff University

School of Chemistry

Cardiff Catalysis Institute

Cardiff CF10 3AT

UK

Norbert Krause

Dortmund University of Technology

Organic Chemistry II

Otto-Hahn-Straße 6

44227 Dortmund

Germany

Zigang Li

University of Chicago

Department of Chemistry

5735 South Ellis Avenue

Chicago

IL 60635

USA

Yuanhong Liu

Chinese Academy of Sciences

Shanghai Institute of Organic Chemistry

State Key Laboratory of Organometallic Chemistry

354 Fenglin Lu

Shanghai 200032

China

Michele Rossi

Università degli Studi di Milano

Dipartimento di Chimica Inorganica, Metallorganica e Analitica

Via Venezian 21

20133 Milan

Italy

Matthias Rudolph

Universität Heidelberg

Organisch-Chemisches Institut

Im Neuenheimer Feld 270

69120 Heidelberg

Germany

F. Dean Toste

University of California, Berkeley

Department of Chemistry

Latimer Hall

Berkeley

CA 94720

USA

Christian Winter

Dortmund University of Technology

Organic Chemistry II

Otto-Hahn-Straße 6

44227 Dortmund

Germany

Yoshinori Yamamoto

Tohoku University

Graduate School of Science

Department of Chemistry

Sendai 980-8578

Japan