N-Heterocyclic Carbenes

Preface

N-HETEROCYCLIC CERBENES
Introduction
Structure and Properties of NHCs
Abnormal Carbenes
Why Are NHCs Stable?
Bonding of NHCs to Metal Centers
Quantifying the Properties of NHCs
N-Heterocyclic Carbenes in the Context of Other Stable Carbenes
Synthesis of NHCs
Salts and Adducts of NHCs
Summary

TUNING AND QUANTIFYING STERIC AND ELECTRONIC EFFECTS OF N-HETEROCYCLIC CARBENES
Introduction
Steric Effects in NHC ligands
Electronic Effects in NHC Ligands
Conclusions

CHIRAL MONODENDATE N-HETEROCYCLIC CARBENE LIGANDS IN ASYMMETRIC CATALYSIS
Introduction
NHC-Ru
NHC-Rh
NHC-Ir
NHC-Ni
NHC-Pd
NHC-Cu
NHC-Ag
NHC-Au
Conclusion

(N-HETEROCYCLIC CARBENE)-PALLADIUM COMPLEXES IN CATALYSIS
Introduction
Cross-Coupling Reactions
Chelates and Pincer Ligands
Asymmetric Catalysis
Oxidation Reactions
Telomerization, Oligomerization and Polymerization
Anticancer NHC-Pd Complexes

NHC PLATINUM(0) COMPLEXES: UNIQUE CATALYSTS FOR THE HYDROSILYLATION OF ALKENES AND ALKYNES
Introduction
Hydrosilylation of Alkenes: The Beginning
Initial Results with Phosphine Ligands
NHC Platinum(0) Complexes: The Breakthrough
Hydrosilylation of Alkynes
Conclusions

SYNTHESIS AND MEDICINAL PROPERTIES OF SILVER-NHC COMPLEXES AND IMIDAZOLIUM SALTS
Introduction
Silver-NHC Complexes as Antimicrobial Agents
Silver-NHC Complexes as Anticancer Agents
Conclusions

MEDICAL APPLICATIONS OF NHC-GOLD AND -COPPER COMPLEXES
Introduction
Gold Antimicrobial Agents
Metals as Antitumor Reagents
Copper Complexes as Antitumoral Reagents
Conclusion

NHC-COPPER COMPLEXES AND THEIR APPLICATIONS
Introduction
History of NHC-Copper Systems
Hydrosilylation
Allene Formation
1,4-Reduction
Conjugate Addition
Hydrothiolation, Hydroalkoxylation, Hydroamination
Carboxylation and Carbonylation (via Boronic Acids, CH Activation): CO2 Insertion
[3 + 2] Cycloaddition Reaction: Formation of Triazole
Allylic Substitution
Carbene and Nitrene Transfer
Boration Reaction
Olefination of Carbonyl Derivatives
Copper-Mediated Cross-Coupling Reaction
Fluoride Chemistry
Other Reactions
Transmetalation
Conclusion

NHC-AU(I) COMPLEXES: SYNTHESIS, ACTIVATION, AND APPLICATION
Introduction
Synthesis of NHC-Gold(I) Chlorides
Activation of NHC-Au(I) Chlorides
Applications of NHC-Au(I) Catalysts
Conclusion

RECENT DEVELOPMENTS IN THE SYNTHESIS AND APPLICATIONS OF RHODIUM AND IRIDIUM COMPLEXES BEARING N-HETEROCYCLIC CARBENE LIGANDS
Introduction
Rh- and Ir-NHC-Based Complexes: Structural and Electronic Features Mono-NHCs
Catalytic Applications of Rhodium and Iridium NHC-Based Complexes
Abbreviations

N-HETEROCYCLIC CARBENE?RUTHNIUM COMPLEXES: A PROMINENT BREAKTHROUGH IN METATHESIS REACTIONS
Introduction
Variations of NHC in Ruthenium Complexes
Modifications in Imidazol- and Imidazolin-2-ylidene Ligands
Influence of Symmetrically 1,3-Substituted N-Heterocyclic Carbene in Metathesis
Unsymmetrically N,N'-Substituted N-Heterocyclic Carbenes

RUTHENIUM N-HETEROCYCLIC CARBENE COMPLEXES FOR THE CATALYSIS OF NONMETATHESIS ORGANIC TRANSFORMATIONS
Introduction
Transfer Hydrogenation
Direct Hydrogenation (and Hydrosilylation)
Borrowing Hydrogen
Alcohol Racemization
Arylation
Reactions of Alkynes
Isomerization of C=C Bonds
Allylic Substitution Reactions
Miscellaneous Reactions
Conclusions

NICKEL COMPLEXES OF N-HETEROCYCLIC CARBENES
Introduction
Nickel-NHC Catalysts
Cross-Coupling Reactions
Oxidation/Reduction Reactions
Hydrosilylation
Cycloadditions
Isomerization
Reductive Coupling
Conclusions and Outlook

COODINATION CHEMISTRY, RACTIVITY, AND APPLICATIONS OF EARLY TRANSITION METAL COMPLEXES BEARING N-HETEROCYCLIC CARBENE LIGANDS
Introduction
Group 3 Metal Complexes
Group 4 Metal Complexes
Group 5 Metal Complexes
Group 6 Metal Complexes
Group 7 Metal Complexes
Conclusion

NHC COMPLEXES OF MAIN GROUP ELEMNTES: NOVEL STRUCTURES, REACTIVITY, AND CATALYTIC BEHAVIOR
Introduction
Structures of Common NHCs for Main Group Chemi