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Functionalised N-Heterocyclic Carbene Complexes



Functionalised N-Heterocyclic Carbene Complexes

Olaf Kühl

ISBN: 978-0-470-71215-3 March 2010 364 Pages


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.



Chapter 1 The Nature of N-Heterocyclic Carbenes.

1.1 Synthesis.

1.2 Properties of NHC.


Chapter 2 Why Functionalisation?

2.1 Phosphane Mimick.

2.2 Hemilability.

2.3 Chirality.

2.4 Ligand Geometry.

2.5 Catalysis.


Chapter 3 N-Heterocyclic with Neutral Tethers.

3.1 Amine Functionalities.

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 with Anionic Functional Groups.

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.


Chapter 6 Natural Products.

6.1 Thiazole.

6.2 Amino Acids.

6.3 Purines and Xanthines.

6.4 Carbohydrates.

6.5 Miscellaneous.



Applied Organometallic Chemistry