Transition-metal-mediated Aromatic Ring Construction

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  • Format: Hardcover
  • Copyright: 2013-08-19
  • Publisher: Wiley

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State-of-the-science methods, synthetic routes, and strategies to construct aromatic rings

The development of new reactions for the synthesis of aromatic compounds is a highly active research area in organic synthesis, providing new functional organic materials, functional reagents, and biologically active compounds. Recently, significant advances in transition-metal-mediated reactions have enabled the efficient and practical construction of new aromatic rings with useful properties and applications. This book draws together and reviews all the latest discoveries and methods in transition-metal-mediated reactions, offering readers promising new routes to design and construct complex aromatic compounds.

Integrating metal catalysis with aromatic compound synthesis, Transition-Metal-Mediated Aromatic Ring Construction offers a practical guide to the methods, synthetic routes, and strategies for constructing aromatic compounds. The book's five parts examine:

  • [2+2+2], [2+2+1], and related cycloaddition reactions
  • [4+2], [3+2], and related cycloaddition reactions
  • Electrocyclization reactions
  • Coupling and addition reactions
  • Other important transformations, including methathesis reactions and skeletal rearrangement reactions

Edited by Ken Tanaka, an internationally recognized expert in the field of transition-metal catalysis, the book features authors who are leading pioneers and researchers in synthetic reactions. Their contributions reflect a thorough review and analysis of the literature as well as their own firsthand laboratory experience developing new aromatic compounds.

All chapters end with a summary and outlook, setting forth new avenues of research and forecasting new discoveries. There are also references at the end of each chapter, guiding readers to important original research reports and reviews.

In summary, Transition-Metal-Mediated Aromatic Ring Construction offers synthetic chemists a promising new avenue for the development of important new aromatic compounds with a broad range of applications.

Author Biography

KEN TANAKA is Professor in the Department of Applied Chemistry at the Tokyo University of Agriculture and Technology. Previously, he worked for the Mitsubishi Chemical Corporation in organic process research. Dr. Tanaka has published more than 100 scientific papers concerning transition-metal catalysis.

Table of Contents

Part 1: [2+2+2], [2+2+1], and Related Cycloaddition Reactions

Chapter 1: Cobalt-Mediated [2+2+2] Cycloaddition
Vincent Gandon

1.1 Introduction

1.2 Synthesis of Benzenes

1.3 Synthesis of Heterocycles

1.4 Mechanistic Aspects

1.5 Synthetic Applications

1.6 Summary and Outlook

1.7 References

Chapter 2: Nickel-Mediated [2+2+2] Cycloaddition
Puneet Kumar and Janis Louie

2.1 Introduction

2.2 Synthesis of Benzenes

2.3 Cycloaddition of Alkynes and Nitriles

2.4 Cycloaddition of Alkynes and Imines

2.5 Cycloaddition of Alkynes and Carbon-Dioxide

2.6 Cycloaddition of Alkynes and Isocyanates

2.7 Cycloaddition of Alkynes and Carbodiimide

2.8 Cycloaddition of Diynes and Ketenes

2.9 Cycloaddition of Arynes

2.10 Mechanism

2.11 Summary and Outlook

2.12 References

Chapter 3: Ruthenium-Mediated [2+2+2] Cycloaddition
Yoshihiko Yamamoto

3.1 Introduction

3.2 Synthesis of Benzenes

3.3 Syntheses of Heterocycles

3.4 Mechanism of Ruthenium-Catalyzed [2+2+2] Cycloadditions

3.5 Synthetic Applications

3.6 Summary and Outlook

3.7 References

Chapter 4: Rhodium-Mediated [2+2+2] Cycloaddition
Ken Tanaka

4.1 Introduction

4.2 Synthesis of Benzenes

4.3 Synthesis of Pyridines

4.4 Synthesis of Pyridones and Related Heterocycles

4.5 Summary and Outlook

4.6 References

Chapter 5: Iridium-Mediated [2+2+2] Cycloaddition
Ryo Takeuchi

5.1 Introduction

5.2 Synthesis of Benzene Derivatives

5.3 Synthesis of Heterocyclic Compounds

5.4 Mechanistic Aspects

5.5 Summary and Outlook

5.6 References

Chapter 6: [2+2+2], [2+2+1], and Related Cycloadditions Mediated by Other Transition Metals
Ken Tanaka and Yu Shibata

6.1 Introduction

6.2 Palladium-Catalyzed [2+2+2] and [2+2+1] Cycloadditions

6.3 Iron-Catalyzed [2+2+2] Cycloaddition

6.4 Manganese-Catalyzed [2+2+2] Cycloaddition

6.5 Rhenium-Catalyzed [2+2+2], [2+1+2+1], and [2+2+1+1] Cycloadditions

6.6 Other Transition-Metals-Catalyzed [2+2+2] Cycloaddition

6.7 Summary and Outlook

6.8 References

Chapter 7: Application to the Synthesis of Natural Products
Julien Grand and Bernhard Witulski

7.1 Introduction

7.2 Construction of Benzene Rings

7.3 Construction of Heterocyclic Rings

7.4 Miscellaneous

7.5 Summary and Outlook

7.6 References

Chapter 8: Synthesis of Planar Chiral Aromatic Compounds via [2+2+2] Cycloaddition
Takanori Shibata and Ken Tanaka

8.1 Introduction

8.2 Cobalt-Catalyzed [2+2+2] Cycloaddition

8.3 Rhodium-Catalyzed [2+2+2] Cycloaddition

8.4 Enantioselective [2+2+2] Cycloaddition

8.5 Summary and Outlook

8.6 References

Chapter 9: Synthesis of Axially Chiral Aromatic Compounds via [2+2+2] Cycloaddition
Ken Tanaka and Takanori Shibata

9.1 Introduction

9.2 Cobalt-Catalyzed Enantioselective [2+2+2] Cycloaddition

9.3 Iridium-Catalyzed Enantioselective [2+2+2] Cycloaddition

9.4 Rhodium-Catalyzed Enantioselective [2+2+2] Cycloaddition

9.5 Enantioselective Synthesis of Axially Chiral Anilides and Bezamides

9.6 Summary and Outlook

9.7 References

Chapter 10: Synthesis of Helically Chiral Aromatic Compounds via [2+2+2] Cycloaddition
Ken Tanaka

10.1 Introduction

10.2 Non-Asymmetric Synthesis

10.3 Diastereoselective Synthesis

10.4 Enantioselective Synthesis

10.5 Summary and Outlook

10.6 References

Chapter 11: Aromatic Ring Construction from Zirconocenes and Titanocenes
Shi Li and Tamotsu Takahashi

11.1 Introduction

11.2 Aromatic Ring Construction from Zirconocenes

11.3 Aromatic Ring Construction from Titanocenes

11.4 Application to Synthesis of Substituted Acenes

11.5 Summary and Outlook

11.6 References

Part 2: [4+2], [3+2], and Related Cycloaddition Reactions

Chapter 12: [4+2] and [3+2] Cycloadditions via Metallacycles
Takuya Kurahashi and Seijiro Matsubara

12.1 Introduction

12.2 [4+2] Cycloaddition via Elimination of Small Molecule

12.3 [3+2] Cycloaddition via Elimination of Small Molecule

12.4 [4+2] Cycloaddition via C–C Bond Activation

12.5 [4+2] Cycloaddition via C–H Bond Activation

12.6 Summary and Outlook

12. 7 References

Chapter 13: Diels-Alder Reactions
Gerhard Hilt

13.1 Introduction

13.2 Transition-Metal-Mediated Diels-Alder Reaction / Aromatization Sequence

13.3 Intramolecular Diels-Alder Reactions toward Dihydroaromatic and Aromatic Products

 13.4 Synthetic Applications

 13.5 Summary and Outlook

 13.6 References

Chapter 14: [4+2] Benzannulation of Enynes with Alkynes
Vladimir Gevorgyan

 14.1 Introduction

 14.2 Benzannulation of Enyne with Alkyne: Au-Catalyzed Benzannulation Reaction

14.3 Benzannulation of Enyne with Enyne

14.4 Benzannulation of Enyne with Diyne

14.5 Synthetic Applications

14.6 Summary and Outlook

14.7 References

Chapter 15: Formal [4+2] Benzannulation via Pyrylium Intermediates
Naoki Asao

 15.1 Introduction

 15.2 Benzannulation of Pyrylium Salts

 15.3 Benzannulation of ortho-Alkynylbenzaldehydes

 15.3.1 With Alkynes

 15.4 Intramolecular [4+2] Benzannulation

 15.5 Application to Natural Product Synthesis

 15.6 Summary and Outlook

 15.7 References

Chapter 16: Utilization of 1,3-Dipolar Compounds
Shunsuke Chiba

 16.1 Introduction

 16.2 1,3-Dipolar Cycloaddition

 16.3 Five-Membered Ring Construction via Decomposition of Azides

 16.4 Six-Membered Ring Construction via Decomposition of Azides

 16.5 Summary and Outlook

16.6 References

Chapter 17: Utilization of Transition-Metal Carbenoids
James Wallace Herndon

 17.1 Introduction

 17.2 Five-Membered Aromatic Ring Construction

 17.3 Six-Membered Aromatic Ring Construction

17.4 Summary and Outlook

17.5 References

Part 3: Electrocyclization Reactions

 Chapter 18: Intramolecular Hydroarylation of Alkynes, Alkenes, and Allenes
Tsugio Kitamura

18.1 Introduction

 18.2 Intramolecular Hydroarylation

 18.3 Summary and Outlook

18.4 References

Chapter 19: Intramolecular C–X Bond Formation between C=X or X–H and Alkynes
Hiroaki Ohno

 19.1 Introduction

 19.2 C−X Bond Formation between C=X and Alkynes

 19.2.1 Pyridine Formation

 19.3 C−X Bond Formation between X−H and Alkynes

 19.4 Summary and Outlook

19.5 References

 Chapter 20: Synthesis of Heterocycles via X–H Bond Addition to Diynes
Takanori Matsuda

 20.1 Introduction

 20.2 Synthesis of Pyrroles and Furans via Double trans-Addition to 1,3-Diynes

 20.3 Synthesis of Pyrroles via Hydroamination of 1,4- and 1,5-Diynes

 20.4 Synthesis of Siloles and Germoles via Double trans-Addition to 1,3-Diynes

 20.5 Summary and Outlook

 20.6 References

Chapter 21: Cyclization via Transition-Metal Cumulenylidenes
Yoshiaki Nishibayashi

 21.1 Introduction

 21.2 Cycloaromatization via Chromium-, Molybdenum-, and Tungsten-Vinylidene Complexes

 21.3 Cycloaromatization via Ruthenium-Vinylidene Complexes

 21.4 Cycloaromatization via Rhodium-Vinylidene Complexes

21.5 Cycloaromatization via Gold-Vinylidene Complexes

 21.6 Cycloaromatization via Ruthenium-Allenylidene Complexes

 21.7 Summary and Outlook

21.8 References

Part 4: Coupling and Addition Reactions

 Chapter 22: C-C Bond Forming Coupling Reactions
Masaki Shimizu

 22.1 Introduction

 22.2 Cyclization

 22.3 Annulation

 22.4 Summary and Outlook

 22.5 References

 Chapter 23: Synthesis of Carbazoles and Related Compounds via C-X Bond Forming Coupling Reactions
Koji Nakano

23.1 Introduction

23.2 Synthesis of Carbazoles

23.3 Synthesis of Dibenzofurans and Dibenzothiophenes

23.4 Synthesis of Other Dibenzoheteroles

23.5 Summary and Outlook

23.6 References

Chapter 24: Synthesis of Aromatic Benzo-Fused Five- and Six-Membered Heterocycles via Palladium- and Copper-Catalysed C-X Bond Forming Reactions
Catherine J. Ball and Michael C. Willis

 24.1 Introduction

 24.2 C-N Bond Formation

 24.3 C-O Bond Formation

 24.4 C-S Bond Formation

 24.5 Annulation of Anilines and Related Compounds with Alkynes

 24.6 Summary and Outlook

 24.7 References

Chapter 25: Coupling Reactions of sp2 C–H Bond with Alkynes
Tetsuya Satoh and Masahiro Miura

25.1 Introduction

25.2 Synthesis of Arenes

25.3 Synthesis of Heterocycles

25.4 Summary and Outlook

25.5 References

Part 5: Other Important Transformations

 Chapter 26: Methathesis Reactions
Kazuhiro Yoshida

 26.1 Introduction

 26.2 Alkene Methathesis

 26.3 Ene-Yne Methathesis

 26.4 Other Applications

 26.5 Summary and Outlook

 26.6 References and Notes

Chapter 27: Skeletal Rearrangement Reactions
Itaru Nakamura

 27.1 Introduction

 27.2 π-Electrophilic Transition-Metal-Mediated Aromatization Reactions

27.3 σ-Electrophilic Transition-Metal-Mediated Aromatization Reactions

27.4 Synthetic Applications

 27.5 Summary and Outlook

27.6 References

Chapter 28: Dearomatization-Aromatization Sequence
Hiroto Yoshida

 28.1 Introduction

 28.2 Reactions via Arynes

 28.3 Reactions via ortho-Quinodimethanes

 28.4 Summary and Outlook

 28.5 References

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