Functionalised N-Heterocyclic Carbene Complexes / Edition 1

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N-heterocyclic carbenes (NHCs) have found increasing use as reagents for a range of organic transformations and in asymmetric organocatalysis. The performance of these molecules can be improved and tuned by functionalisation. Functionalised carbenes can anchor free carbenes to the metal site, introduce hemilability, provide a means to immobilise transition metal carbene catalysts, introduce chirality, provide a chelate ligand or bridge two metal centres. NHC can be attached to carbohydrates and campher, derived from amino acids and purines, they can be used as organocatalysts mimicking vitamin B1 or as weak “solvent” donors in lanthanide chemistry.

Functionalised N-Heterocyclic Carbene Complexes describes major trends in functionalised NHC ligands, aiming to assist readers in their attempts to develop and apply their own functionalised carbenes. After an introduction to the chemistry and behaviour of NHC, the book gives a detailed description of functionalised carbenes and their complexes according to a range of functional groups, each with a discussion of the synthetic route, structure, stability and performance.

Functionalised N-Heterocyclic Carbene Complexes is an essential guide to fine-tuning this important class of compounds for practitioners, researchers and advanced students working in synthetic organometallic and organic chemistry and catalysis.

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Applied Organometallic Chemistry
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Product Details

  • ISBN-13: 9780470712153
  • Publisher: Wiley
  • Publication date: 3/15/2010
  • Edition number: 1
  • Pages: 364
  • Product dimensions: 6.80 (w) x 9.90 (h) x 1.00 (d)

Table of Contents

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


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


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


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


Chapter 5 Chiral N-Heterocyclic Carbenes 279


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


Index 347

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