Functionalised N-Heterocyclic Carbene Complexes Book

Abbreviations vii

Introduction 1

Chapter 1 The Nature of N-Heterocyclic Carbenes 7

1.1 Synthesis

1.1.1 Synthesis of the Imidazolium Salts

1.1.2 Closing the Ring

1.1.3 Synthesis of the Free Carbenes

1.1.4 Synthesis of Transition Metal Complexes of NHC

1.2 Properties of NHC

1.2.1 The Internal Electronic Structure

1.2.2 Basicity of NHC

1.2.3 Steric Properties

1.2.4 The Carbene-Metal Bond

1.2.5 Decomposition Pathways

References

Chapter 2 Why Functionalisation?

2.1 Phosphane Mimic

2.2 Hemilability

2.3 Chirality

2.3.1 Planar Chirality

2.3.2 Axial Chirality

2.4 Ligand Geometry

2.5 Catalysis

2.5.1 Allylic Alkylation

2.5.2 Coupling Reactions

2.5.3 Olefin Metathesis

2.5.4 Polymerisations

2.5.5 Organocatalysis

References

Chapter 3 N-Heterocyclic Carbenes with Neutral Tethers

3.1 Amine Functionalities

3.1.1 Heteroaromatic Functional Groups

3.1.2 Oxazolines

3.1.3 Imino Functional Groups

3.1.4 Amino Functionalised NHC

3.2 Oxygen-Containing Groups

3.3 Phosphane Functionalities

3.4 Bis-Carbene Ligands

3.5 Tris-N-Heterocyclic Carbene Ligands

3.6 Pincer Carbenes

References

Chapter 4 N-Heterocyclic Carbenes with Anionic Functional Groups 199

4.1 Oxygen-Containing Groups

4.2 Nitrogen-Containing Groups

4.3 NHC Ligands Incorporating Cp Moieties

4.4 Transition Metal NHC Complexes Involved in the Activation of C-H Bonds

4.5 Immobilisation of the Catalyst

4.6 Sulfur-Containing Functional Groups

References

Chapter 5 Chiral N-Heterocyclic Carbenes 279

References

Chapter 6 Natural Products 309

6.1 Thiazole

6.1.1 Isolation and Stability of Thiazolylidene

6.1.2 Benzothiazoles

6.1.3 Metal Complexes

6.2 Amino Acids

6.3 Purines and Xanthines

6.4 Carbohydrates

6.5 Miscellaneous

References

Index 347