Catalytic Arylation Methods E-Book

Anthony J. Burke

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

Seitenzahl: 769

Veröffentlichungsjahr: 2014

Beschreibung

This "hands-on" approach to the topic of arylation consolidates the body of key research over the last ten years (and up to around 2014) on various catalytic methods which involve an arylation process. Clearly structured, the chapters in this one-stop resource are arranged according to the reaction type, and focus on novel, efficient and sustainable processes, rather than the well-known and established cross-coupling methods. The entire contents are written by two authors with academic and industrial expertise to ensure consistent coverage of the latest developments in the field, as well as industrial applications, such as C-H activation, iron and gold-catalyzed coupling reactions, cycloadditions or novel methodologies using arylboron reagents. A cross-section of relevant tried-and-tested experimental protocols is included at the end of each chapter for putting into immediate practice, along with patent literature. Due to its emphasis on efficient, "green" methods and industrial applications of the products concerned, this interdisciplinary text will be essential reading for synthetic chemists in both academia and industry, especially in medicinal and process chemistry.

Leseprobe

Table of Contents

Cover

Related Titles

Title Page

Copyright

Dedication

Preface

List of Abbreviations

Chapter 1: Cross-Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

1.1 Metal-Catalyzed Cross-Couplings: From Its Origins to the Nobel Prize and Beyond

1.2 Arylation: What Is So Special?

1.3 Recent New Developments

1.4 Selected Experiments from the Literature

References

Chapter 2: Amine, Phenol, Alcohol, and Thiol Arylation

2.1 Introduction

2.2 Pd-Catalyzed Processes

2.3 Cu-Catalyzed and Promoted Arylations: (C

Ar

–N Bond Formation)

2.4 Fe-Catalyzed Arylations

2.5 Ni-Catalyzed Reactions

2.6 Co-Catalyzed Arylations

2.7 Mn-Catalyzed Arylations

2.8 Cd-Catalyzed Arylations

2.9 Bi(III) and Indium Oxide-Catalyzed Thiol Arylations

2.10 Conclusions and Final Comment

2.11 Selected Experiments from the Literature

References

Chapter 3: Decarboxylative Coupling Techniques

3.1 Introduction

3.2 Pd-Catalyzed Versions

3.3 Other Metal-Catalyzed Versions

3.4 Conclusions

3.5 Selected Experiments

References

Chapter 4: C–H Bond Activation for Arylations

4.1 Introduction

4.2 C(sp

2

)–H Activations

4.3 Conclusions

4.4 Selected Experiments from the Literature

References

Chapter 5: Conjugate Additions

5.1 Conjugate Additions: A Powerful Tool for Appending Organic Residues to Cyclic and Acyclic Substrates

5.2 Applications of Rh Catalysts

5.3 Applications of Pd Catalysts

5.4 Applications of Ru and Other Catalysts

5.5 Conclusions

5.6 Selected Experiments

References

Chapter 6: Imine Arylations – Synthesis of Arylamines

6.1 Arylation of C=N Bonds: Simple Access to Chiral Amine Units

6.2 Application of Rh Catalysts

6.3 Application of Pd Catalysts

6.4 Application of Ru and Other Catalysts

6.5 The Petasis–Akritopoulou Reaction

6.6 Conclusions

6.7 Selected Experiments

References

Chapter 7: Carbonyl Group Arylation

7.1 Introduction

7.2 Application of Rh Catalysts

7.3 Application of Pd Catalysts

7.4 Application of Ru and Other Catalysts

7.5 Conclusions

7.6 Selected Experiments

References

Chapter 8: α-Arylation Processes

8.1 Introduction

8.2 Arylation of Enolates and Equivalents

8.3 Other Metal-Catalyzed α-Arylations

8.4 Conclusions

8.5 Selected Experiments

References

Chapter 9: Catalytic Cycloaddition Aromatization Processes

9.1 Introduction

9.2 Cycloaddition Events

9.3 Radical-Based Cycloaromatization Processes

9.4 Conclusions

9.5 Selected Experiments from the Literature

References

Index

End User License Agreement

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Guide

Cover

Table of Contents

Preface

Chapter 1: Cross-Coupling Arylations: Precedents and Rapid HistoricalReview of the Field

List of Illustrations

Scheme 1.1

Figure 1.1

Scheme 1.2

Scheme 1.3

Scheme 1.4

Scheme 1.5

Scheme 1.6

Scheme 1.7

Scheme 1.8

Scheme 1.9

Scheme 1.10

Scheme 1.11

Scheme 1.12

Scheme 1.13

Scheme 1.14

Scheme 1.15

Scheme 1.16

Scheme 1.17

Figure 1.2

Scheme 1.18

Figure 1.3

Figure 1.4

Figure 1.5

Figure 1.6

Scheme 1.19

Scheme 1.20

Figure 1.7

Figure 1.8

Scheme 1.21

Figure 1.9

Figure 1.10

Figure 1.11

Figure 1.12

Figure 1.13

Figure 1.14

Figure 1.15

Scheme 1.22

Figure 1.16

Scheme 1.23

Scheme 1.24

Scheme 1.25

Scheme 1.26

Figure 1.17

Scheme 1.27

Scheme 1.28

Figure 1.18

Figure 1.19

Figure 1.20

Figure 1.21

Figure 1.22

Scheme 1.29

Scheme 1.30

Figure 1.23

Scheme 1.31

Figure 1.24

Scheme 1.32

Scheme 1.33

Figure 1.25

Figure 1.26

Figure 1.27

Figure 1.28

Scheme 1.34

Scheme 1.35

Scheme 1.36

Scheme 1.37

Scheme 1.38

Scheme 1.39

Figure 1.29

Figure 1.30

Figure 1.31

Figure 1.32

Figure 1.33

Figure 1.34

Scheme 1.40

Figure 1.35

Figure 1.36

Figure 1.37

Scheme 1.41

Figure 1.38

Figure 1.39

Figure 1.40

Figure 1.41

Figure 1.42

Figure 1.43

Scheme 1.42

Scheme 1.43

Scheme 1.44

Scheme 1.45

Figure 1.44

Scheme 1.46

Scheme 1.47

Scheme 1.48

Figure 1.45

Scheme 1.49

Figure 1.46

Scheme 1.50

Figure 1.47

Scheme 1.51

Scheme 1.52

Scheme 1.53

Scheme 1.54

Scheme 1.55

Scheme 1.56

Scheme 1.57

Scheme 1.58

Figure 1.48

Figure 1.49

Figure 2.1

Figure 2.2

Scheme 2.1

Scheme 2.2

Figure 2.3

Figure 2.4

Scheme 2.3

Scheme 2.4

Scheme 2.5

Figure 2.5

Figure 2.6

Scheme 2.6

Scheme 2.7

Scheme 2.8

Figure 2.7

Scheme 2.9

Figure 2.8

Scheme 2.10

Scheme 2.11

Figure 2.9

Scheme 2.12

Figure 2.10

Figure 2.11

Figure 2.12

Figure 2.13

Scheme 2.13

Figure 2.14

Scheme 2.14

Figure 2.15

Figure 2.16

Scheme 2.15

Scheme 2.16

Figure 2.17

Scheme 2.17

Figure 2.18

Scheme 2.18

Figure 2.19

Figure 2.20

Scheme 2.19

Scheme 2.20

Figure 2.21

Figure 2.22

Figure 2.23

Scheme 2.21

Scheme 2.22

Scheme 2.23

Scheme 2.24

Scheme 2.25

Scheme 2.26

Scheme 2.27

Scheme 2.28

Figure 2.24

Figure 2.25

Scheme 2.29

Figure 2.26

Figure 2.27

Scheme 2.30

Figure 2.28

Figure 2.29

Scheme 2.31

Scheme 2.32

Scheme 2.33

Scheme 3.1

Figure 3.1

Scheme 3.2

Scheme 3.3

Scheme 3.4

Scheme 3.5

Scheme 3.6

Scheme 3.7

Scheme 3.8

Scheme 3.9

Scheme 3.10

Scheme 3.11

Scheme 3.12

Scheme 3.13

Scheme 3.14

Scheme 3.15

Scheme 3.16

Scheme 3.17

Scheme 3.18

Scheme 3.19

Scheme 3.20

Scheme 3.21

Scheme 3.22

Scheme 3.23

Scheme 3.24

Scheme 3.25

Scheme 3.26

Figure 4.1

Figure 4.2

Figure 4.3

Figure 4.4

Figure 4.5

Figure 4.6

Figure 4.7

Scheme 4.1

Scheme 4.2

Figure 4.8

Scheme 4.3

Figure 4.9

Scheme 4.4

Figure 4.10

Scheme 4.5

Figure 4.11

Figure 4.12

Figure 4.13

Scheme 4.6

Scheme 4.7

Figure 4.14

Figure 4.15

Figure 4.16

Figure 4.17

Figure 4.18

Figure 4.19

Figure 4.20

Figure 4.21

Scheme 4.8

Figure 4.22

Figure 4.23

Figure 4.24

Figure 4.25

Scheme 4.9

Figure 4.26

Scheme 4.10

Figure 4.27

Figure 4.28

Figure 4.29

Figure 4.30

Figure 4.31

Figure 4.32

Figure 4.33

Figure 4.34

Figure 4.35

Figure 4.38

Figure 4.36

Figure 4.37

Figure 4.39

Figure 4.40

Figure 4.41

Figure 4.42

Figure 4.43

Figure 4.44

Figure 4.45

Scheme 4.11

Scheme 4.12

Scheme 4.13

Scheme 4.14

Figure 4.46

Scheme 4.15

Scheme 4.16

Figure 4.47

Scheme 4.17

Figure 4.48

Figure 4.49

Figure 4.50

Figure 4.51

Scheme 4.18

Scheme 4.19

Scheme 4.20

Scheme 4.21

Scheme 4.22

Scheme 5.1

Scheme 5.2

Scheme 5.3

Scheme 5.4

Figure 5.1

Scheme 5.5

Figure 5.2

Figure 5.3

Scheme 5.6

Figure 5.4

Scheme 5.7

Figure 5.5

Scheme 5.8

Figure 5.6

Figure 5.7

Figure 5.8

Scheme 5.9

Scheme 5.10

Figure 5.9

Figure 5.10

Scheme 5.11

Figure 5.11

Figure 5.12

Figure 5.13

Scheme 5.12

Scheme 5.13

Figure 5.14

Figure 5.15

Figure 5.16

Scheme 5.14

Figure 5.17

Scheme 5.15

Scheme 5.16

Scheme 5.17

Scheme 5.18

Figure 5.18

Scheme 5.19

Scheme 5.20

Scheme 5.21

Figure 5.22

Scheme 5.23

Figure 5.19

Scheme 5.24

Scheme 5.25

Scheme 5.26

Scheme 5.27

Figure 5.20

Scheme 5.28

Scheme 5.29

Scheme 5.30

Scheme 5.31

Figure 5.21

Scheme 5.32

Scheme 5.33

Scheme 5.34

Scheme 5.35

Scheme 5.36

Figure 5.22

Scheme 5.37

Figure 5.23

Figure 5.24

Scheme 5.38

Scheme 5.39

Scheme 5.40

Figure 6.1

Scheme 6.1

Schemes 6.2

Figure 6.3

Scheme 6.4

Scheme 6.5

Scheme 6.6

Scheme 6.7

Scheme 6.8

Scheme 6.9

Scheme 6.10

Scheme 6.11

Figure 6.2

Scheme 6.12

Scheme 6.13

Scheme 6.14

Scheme 6.15

Scheme 6.16

Scheme 6.17

Scheme 6.18

Scheme 6.19

Scheme 6.20

Scheme 6.21

Scheme 6.22

Scheme 6.23

Scheme 6.24

Scheme 6.25

Scheme 6.26

Scheme 6.27

Scheme 6.28

Scheme 6.29

Scheme 6.30

Scheme 6.31

Scheme 6.32

Scheme 6.33

Scheme 6.34

Scheme 6.35

Scheme 6.36

Scheme 6.37

Scheme 6.38

Scheme 6.39

Scheme 6.40

Scheme 6.41

Scheme 6.42

Scheme 6.43

Figure 6.3

Scheme 6.44

Scheme 6.45

Scheme 6.46

Figure 6.4

Scheme 6.47

Scheme 6.48

Scheme 6.49

Figure 7.1

Scheme 7.1

Scheme 7.2

Scheme 7.3

Scheme 7.4

Scheme 7.5

Scheme 7.6

Figure 7.2

Figure 7.3

Scheme 7.7

Scheme 7.8

Scheme 7.9

Scheme 7.10

Scheme 7.11

Figure 7.4

Scheme 7.12

Scheme 7.13

Scheme 7.14

Scheme 7.15

Scheme 7.16

Figure 7.5

Scheme 7.17

Figure 7.6

Scheme 7.18

Scheme 7.19

Figure 7.7

Scheme 7.20

Scheme 7.21

Scheme 7.22

Scheme 7.23

Scheme 7.24

Scheme 7.25

Scheme 7.26

Figure 7.8

Scheme 7.27

Scheme 7.28

Scheme 7.29

Scheme 7.30

Scheme 7.31

Scheme 7.32

Scheme 7.33

Scheme 7.34

Scheme 7.35

Scheme 7.36

Scheme 7.37

Scheme 7.38

Scheme 7.39

Scheme 7.40

Scheme 7.41

Scheme 7.42

Scheme 7.43

Scheme 7.44

Figure 7.9

Scheme 7.45

Scheme 7.46

Scheme 7.47

Scheme 7.48

Scheme 7.49

Scheme 7.50

Scheme 7.51

Figure 7.10

Scheme 7.52

Scheme 8.1

Figure 8.1

Scheme 8.2

Scheme 8.3

Scheme 8.4

Scheme 8.5

Scheme 8.16

Scheme 8.17

Figure 8.2

Scheme 8.18

Scheme 8.19

Scheme 8.20

Scheme 8.21

Figure 8.3

Scheme 8.22

Scheme 8.23

Scheme 8.24

Scheme 8.25

Scheme 8.26

Scheme 8.27

Scheme 8.28

Figure 8.4

Scheme 8.29

Scheme 8.30

Scheme 8.31

Scheme 8.32

Scheme 8.33

Scheme 8.34

Scheme 8.35

Scheme 8.36

Scheme 8.37

Scheme 8.38

Figure 8.5

Scheme 8.39

Scheme 8.40

Scheme 8.41

Scheme 8.42

Scheme 8.43

Figure 8.6

Scheme 8.44

Scheme 8.45

Scheme 8.46

Scheme 8.47

Scheme 8.48

Scheme 8.49

Scheme 8.50

Scheme 8.51

Scheme 8.52

Figure 8.53

Scheme 8.54

Figure 8.7

Scheme 8.55

Scheme 8.56

Scheme 8.57

Scheme 8.58

Scheme 8.59

Scheme 8.60

Scheme 8.61

Scheme 8.62

Scheme 8.63

Scheme 8.64

Figure 8.8

Scheme 8.65

Scheme 8.66

Scheme 8.67

Scheme 8.68

Scheme 8.69

Scheme 8.70

Scheme 8.71

Scheme 8.72

Scheme 8.73

Scheme 8.74

Scheme 8.75

Scheme 8.76

Scheme 8.77

Figure 9.1

Figure 9.2

Scheme 9.2

Scheme 9.1

Figure 9.3

Scheme 9.3

Scheme 9.4

Scheme 9.5

Scheme 9.6

Scheme 9.7

Scheme 9.8

Scheme 9.9

Scheme 9.10

Scheme 9.11

Figure 9.4

Scheme 9.12

Scheme 9.13

Scheme 9.14

Scheme 9.15

Figure 9.5

Scheme 9.16

Scheme 9.17

Scheme 9.18

Figure 9.6

Scheme 9.19

Figure 9.7

Scheme 9.20

Scheme 9.21

Scheme 9.22

Figure 9.8

Scheme 9.23

Scheme 9.24

Scheme 9.25

Scheme 9.26

Scheme 9.27

Scheme 9.28

Scheme 9.29

Scheme 9.30

Scheme 9.31

Scheme 9.32

Figure 9.9

Figure 9.10

Figure 9.11

Scheme 9.33

Figure 9.12

Scheme 9.34

Scheme 9.35

Figure 9.13

Figure 9.14

Figure 9.15

Scheme 9.36

Scheme 9.37

Scheme 9.38

List of Tables

Table 1.1

Table 1.2

Table 1.3

Table 1.4

Table 8.1

Table 8.3

Table 9.1

Related Titles

de Meijere, A., Bräse, S., Oestreich, M. (eds.)

Metal-Catalyzed Cross-Coupling Reactions and More

2014

ISBN: 978-3-527-33154-3 (Also available in a variety of electronic formats)

Shi, Z. (ed.)

Homogeneous Catalysis for Unreactive Bond Activation

2014

ISBN: 978-1-118-45223-3 (Also available in a variety of electronic formats)

Molnár, Á. (ed.)

Palladium-Catalyzed Coupling Reactions

Practical Aspects and Future Developments

2013

ISBN: 978-3-527-33254-0 (Also available in a variety of electronic formats)

Andersson, P.G. (ed.)

Innovative Catalysis in Organic Synthesis

Oxidation, Hydrogenation,and C-X Bond Forming Reactions

2012

ISBN: 978-3-527-33097-3 (Also available in a variety of electronic formats)

Negishi, E. (ed.)

Handbook of Organopalladium Chemistry for Organic Synthesis

Second Edition

2010

ISBN: 978-0-470-11543-5

Anthony J. Burke and Carolina Silva Marques

Catalytic Arylation Methods

From the Academic Lab to Industrial Processes

The Authors

Prof. Dr. Anthony J. Burke

University of Evora

Chemistry Department and Centro de Química de Évora

Rua Romao Ramalho 59

7000-803 Evora

Portugal

Carolina Silva Marques

University of Evora

Centro de Química de Évora

Rua Romao Ramalho 59

7000-803 Evora

Portugal

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All rights reserved (including those of translation into other languages). No part of this book may be reproduced in any form – by photoprinting, microfilm, or any other means – nor transmitted or translated into a machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law.

Print ISBN: 978-3-527-33518-3

ePDF ISBN: 978-3-527-67274-5

ePub ISBN: 978-3-527-67285-1

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Anthony J. Burke dedicates this book to his late father Dominic, for instilling a curiosity about the world we live in, and his mother Phyllis, for her constant support.

Carolina S. Marques would like to dedicate this book to her parents Lita and Zeca and her sister Gaby.

Preface

Many years ago, one of the authors (AJB) had the pleasure of conducting his first arylation reaction – which was a Heck–Mizoroki reaction between an activated pyrimidine and methyl acrylate – and he was struck by the simplicity and efficacy of the coupling process. Thus, a keen interest in these reactions was awakened, and this has been manifested in the recent research activities conducted in this group.