Transition metal-catalyzed heterocycle synthesis via C-H activation / edited by Xiao-Feng Wu.

Format:

Book

Contributor:

Wu, Xiao-Feng, editor.

Language:

English

Subjects (All):

Transition metal catalysts.

Heterocyclic chemistry.

Chemistry, Organic.

Physical Description:

1 online resource (597 p.)

Edition:

1st ed.

Place of Publication:

Weinheim, Germany : Wiley-VCH Verlag, 2016.

Summary:

Reflecting the tremendous growth of this hot topic in recent years, this book covers C-H activation with a focus on heterocycle synthesis. As such, the text provides general mechanistic aspects and gives a comprehensive overview of catalytic reactions in the presence of palladium, rhodium, ruthenium, copper, iron, cobalt, and iridium. The chapters are organized according to the transition metal used and sub-divided by type of heterocycle formed to enable quick access to the synthetic route needed. Chapters on carbonylative synthesis of heterocycles and the application of C-H activation methodology to the synthesis of natural products are also included. Written by an outstanding team of authors, this is a valuable reference for researchers in academia and industry working in the field of organic synthesis, catalysis, natural product synthesis, pharmaceutical chemistry, and crop protection.

Contents:

Cover

Title Page

Copyright

Dedication

Contents

List of Contributors

Foreword 1

Foreword 2

Preface

Chapter 1 Computational Studies of Heteroatom-Assisted C-H Activation at Ru, Rh, Ir, and Pd as a Basis for Heterocycle Synthesis and Derivatization

1.1 Introduction

1.2 Palladium

1.2.1 Intramolecular Heteroatom-Assisted C-H Activation

1.2.1.1 Early Computational Studies

1.2.1.2 The Role of the Base, Solvent, and Additives on Pd-Mediated Intramolecular C-H Activation

1.2.1.3 Intramolecular C-H Activation of Heterocyclic Substrates

1.2.2 Intermolecular C-H Activation

1.2.2.1 Early Computational Studies

1.2.2.2 Direct Functionalization via C-H Activation of Heterocyclic Substrates

1.3 Ruthenium, Rhodium, and Iridium

1.3.1 Intramolecular Heteroatom-Assisted C-H Activation

1.3.2 Intermolecular C-H Activation

1.3.3 C-H Activation and Functionalization

1.3.3.1 Heterocycle Formation with Internal Oxidants

1.3.3.2 Heterocycle Formation without Internal Oxidants

1.3.4 Alkenylation and Amination

1.4 Conclusions

Acknowledgments

References

Chapter 2 Pd-Catalyzed Synthesis of Nitrogen-Containing Heterocycles

2.1 Introduction

2.2 General Consideration on Palladium Chemistry

2.3 Heterocycle Synthesis via C(sp3)-H Activation

2.3.1 Heterocycle Synthesis via Activated C(sp3)-H Bonds

2.3.2 Heterocycle Synthesis via Unactivated C(sp3)-H Bonds

2.4 Heterocycles via C(sp2)-H Activation

2.5 Conclusions

Chapter 3 Pd-Catalyzed Synthesis of Oxygen-Containing Heterocycles

3.1 Introduction

3.2 Palladium-Catalyzed C-H Activation/C-C Formation to Construct Oxacycles

3.2.1 Palladium-Catalyzed C-H Bond Arylation

3.2.2 Palladium-Catalyzed C-H Olefination

3.2.3 Palladium-Catalyzed C-H Alkylation.

3.2.4 Palladium-Catalyzed C-H Carbonylation and Carboxylation

3.3 Palladium-Catalyzed C-H Activation/C-O Formation to Construct Oxacycles

3.3.1 Palladium-Catalyzed C-O Bond Formation via C(sp2)-H Activation

3.3.2 Palladium-Catalyzed C-O Bond Formation via Allylic C-H Activation

3.4 Conclusions

Chapter 4 Pd-Catalyzed Synthesis of Other Heteroatom-Containing Heterocycles

4.1 Introduction

4.2 Sulfur-Containing Heterocycles

4.2.1 Benzo[b]thiophenes

4.2.2 Benzothiazoles

4.2.3 Sultones

4.2.4 Sultams

4.3 Phosphorus-Containing Heterocycles

4.3.1 P-C Heterocycles (Dibenzophosphole Oxides)

4.3.2 O-P=O Heterocycles

4.3.3 P-N Heterocycles

4.4 Silicon-Containing Heterocycles

4.4.1 Benzosiloles

4.4.2 Oxasiline and Azasiline

4.5 Summary and Conclusions

Chapter 5 Rh-Catalyzed Synthesis of Nitrogen-Containing Heterocycles

5.1 Introduction

5.2 Synthesis of Five-Membered Nitrogen Heterocycles

5.2.1 Synthesis of Indoles

5.2.2 Synthesis of Isoindolines

5.2.3 Synthesis of Unprotected Indoles

5.2.4 Synthesis of Indolines

5.2.5 Synthesis of Indazoles

5.2.6 Synthesis of Isoxazoles

5.2.7 Synthesis of Pyrroles

5.2.8 Synthesis of Isoindolin-1-ones

5.2.9 Synthesis of 3-Hydroxyisoindolin-1-ones

5.2.10 Synthesis of 3-(Imino)isoindolinones

5.2.11 Synthesis of Dihydrocarbazoles

5.2.12 Synthesis of Sultams

5.2.13 Synthesis of Phthalimides

5.3 Synthesis of Six-Membered Nitrogen Heterocycles

5.3.1 Synthesis of Isoquinolines by Rh(I) Catalysis

5.3.2 Synthesis of Isoquinolines by Rh(III) Catalysis

5.3.3 Synthesis of 1-Aminoisoquinolines

5.3.4 Synthesis of Isoquinolones and Related Derivatives

5.3.5 Synthesis of Phenanthridinones

5.3.6 Synthesis of Quinolines

5.3.7 Synthesis of Naphthyridines

5.3.8 Synthesis of Phthalazines.

5.3.9 Synthesis of Acridines and Phenazines

5.3.10 Synthesis of Cinnolines

5.3.11 Synthesis of Isoquinolinones and Cinnolinones

5.3.12 Synthesis of Dihydropyridines

5.3.13 Synthesis of Pyridines

5.3.14 Synthesis of Pyridones

5.3.15 Synthesis of Pyrimidinones

5.4 Synthesis of Quaternary Ammonium Salts

5.4.1 Synthesis of Isoquinolinium Salts

5.4.2 Synthesis of Quinolizinium and Pyridinium Salts

5.4.3 Synthesis of Cinnolinium Salts

5.4.4 Synthesis of Isoquinoline N-Oxides and Pyridine N-Oxides

5.5 Synthesis of Seven-Membered Nitrogen Heterocycles

5.5.1 Synthesis of Azepinones

5.5.2 Synthesis of 1,2-Oxazepines

5.6 Summary and Conclusions

Chapter 6 Rh-Catalyzed Synthesis of Oxygen-Containing Heterocycles

6.1 Introduction

6.2 Synthesis of Five-Membered Oxygen-Containing Heterocycles

6.2.1 Intermolecular Annulation

6.2.1.1 Phthalides

6.2.1.2 Furans

6.2.1.3 Other Five-Membered Oxygen-Containing Heterocycles

6.2.2 Intramolecular Cyclization

6.2.2.1 Dihydrobenzofurans

6.2.2.2 Dibenzofuran

6.3 Synthesis of Six-Membered Oxygen-Containing Heterocycles

6.3.1 Intermolecular Annulation

6.3.1.1 Chromenes

6.3.1.2 Chromones

6.3.1.3 Coumarin

6.3.1.4 Other Six-Membered Oxygen-Containing Heterocycles

6.3.2 Intramolecular Cyclization

6.4 Synthesis of Seven-, Eight-, and Nine-Membered Oxygen-Containing Heterocycles

6.4.1 Intermolecular Annulation

6.4.2 Intramolecular Cyclization

6.5 Summary and Conclusions

Chapter 7 Ruthenium-Catalyzed Synthesis of Heterocycles via C-H Bond Activation

7.1 Introduction

7.2 Ruthenium-Catalyzed Heterocycle Synthesis via Intramolecular C-C Bond Formation Based on C-H Bond Activation

7.3 Ruthenium-Catalyzed Heterocycle Synthesis via Intramolecular C-N Bond Formation Based on C-H Bond Activation.

7.4 Ruthenium-Catalyzed Heterocycle Synthesis via Intermolecular C-C/C-O Bond Formation Based on C-H Bond Activation

7.4.1 Cyclization with Alkynes

7.4.2 Cyclization with Alkenes

7.4.3 Cyclization with Carbon Monoxide

7.4.4 Cyclization with 1,2-Diol

7.5 Ruthenium-Catalyzed Heterocycle Synthesis via Intermolecular C-C/C-N Bond Formation Based on C-H Bond Activation

7.5.1 Cyclization with Alkynes

7.5.2 Cyclization with Alkenes

7.5.3 Cyclization with Carbon Monoxide

7.5.4 Cyclization with Isocyanate

7.6 Summary and Conclusions

Chapter 8 Cu-Catalyzed Heterocycle Synthesis

8.1 Introduction

8.2 Four-Membered-Ring Formation

8.3 Five-Membered-Ring Formation

8.3.1 Copper-Catalyzed Synthesis of Pyrroles

8.3.2 Copper-Catalyzed Synthesis of Pyrrolidines

8.3.3 Copper-Catalyzed Synthesis of Indoles

8.3.4 Copper-Catalyzed Synthesis of Indolines

8.3.5 Copper-Catalyzed Synthesis of Oxindoles

8.3.6 Copper-Catalyzed Synthesis of Indole-2,3-dione (Isatins)

8.3.7 Copper-Catalyzed Synthesis of Indolizines

8.3.8 Copper-Catalyzed Synthesis of Carbazoles

8.3.9 Copper-Catalyzed Synthesis of Imidazoles

8.3.10 Copper-Catalyzed Synthesis of Benzimidazoles

8.3.11 Copper-Catalyzed Synthesis of Imidazopyridines

8.3.12 Copper-Catalyzed Synthesis of Pyrazoles and Indazoles

8.3.13 Copper-Catalyzed Synthesis of Oxazoles

8.3.14 Copper-Catalyzed Synthesis of Benzoxazoles

8.3.15 Copper-Catalyzed Synthesis of 1,2,3-Triazoles

8.3.16 Copper-Catalyzed Synthesis of 1,2,3-Tetrazoles

8.3.17 Copper-Catalyzed Synthesis of Furans

8.4 Six-Membered-Ring Formation

8.4.1 Copper-Catalyzed Synthesis of Pyridines

8.4.2 Copper-Catalyzed Synthesis of Quinolines

8.4.3 Copper-Catalyzed Synthesis of Isoquinolines

8.4.4 Copper-Catalyzed Synthesis of Quinolinones.

8.4.5 Copper-Catalyzed Synthesis of Acridones

8.4.6 Copper-Catalyzed Synthesis of Phenanthridine

8.4.7 Copper-Catalyzed Synthesis of Quinazoline and Quinazolinones

8.4.8 Copper-Catalyzed Synthesis of Cinnolines

8.4.9 Copper-Catalyzed Synthesis of Pyrimidinone

8.4.10 Copper-Catalyzed Synthesis of 1,4-Dihydropyrazine Derivatives

8.4.11 Copper-Catalyzed Synthesis of 1,3-Oxazines

8.4.12 Copper-Catalyzed Synthesis of Oxazinone Derivatives

8.4.13 Copper-Catalyzed Synthesis of Chroman Derivatives

8.4.14 Copper-Catalyzed Synthesis of Benzolactone Derivatives

8.4.15 Copper-Catalyzed Synthesis of Coumarin Derivatives

8.4.16 Copper-Catalyzed Synthesis of Xanthone Derivatives

8.4.17 Copper-Catalyzed Synthesis of N,S-Heterocycles

8.5 Summary

Chapter 9 Fe- and Ag-Catalyzed Synthesis of Heterocycles

9.1 Introduction

9.2 Iron-Catalyzed Synthesis of Heterocycles

9.2.1 Iron-Catalyzed Synthesis of Nitrogen-Containing Heterocycles

9.2.2 Iron-Catalyzed Synthesis of Oxygen-Containing Heterocycles

9.3 Silver-Catalyzed Synthesis of Heterocycles

9.3.1 Silver-Catalyzed Synthesis of Nitrogen-Containing Heterocycles

9.3.2 Silver-Catalyzed Synthesis of Oxygen- or Phosphorus-Containing Heterocycles

9.4 Conclusion and Outlook

Chapter 10 Heterocycles Synthesis via Co-Catalyzed C-H Bond Functionalization

10.1 Introduction

10.2 Heterocycle Synthesis via Low-Valent Cobalt-Catalyzed C-H Activation

10.3 Heterocycle Synthesis via High-Valent Cobalt-Catalyzed C-H Activation

10.4 Heterocycle Synthesis via C-H Functionalization under Co(II)-Based Metalloradical Catalysis

10.5 Summary and Conclusions

Chapter 11 Ir-Catalyzed Heterocycles Synthesis

11.1 Introduction

11.2 Ir-Catalyzed Heterocyclization by ortho-Aryl C-H Activation.

11.2.1 Ir-Catalyzed [3+2] Cyclization of Ketimines with 1,3-Dienes/Alkynes.

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 February 17, 2016).

ISBN:

9783527691920

3527691928

9783527691913

352769191X

OCLC:

933524910