N-Heterocyclic Carbenes

This comprehensive reference and handbook covers in depth all major aspects of the use of N-heterocyclic carbene-complexes in organic synthesis: from the theoretical background to characterization, and from cross-coupling reactions to olefin metathesis. Edited by a leader and experienced scientist in the field of homogeneous catalysis and use of NHCs, this is an essential tool for every academic and industrial synthetic chemist.

This comprehensive reference and handbook covers in depth all major aspects of the use of N-heterocyclic carbene-complexes in organic synthesis: from the theoretical background to characterization, and from cross-coupling reactions to olefin metathesis.Edited by a leader and experienced scientist in the field of homogeneous catalysis and use of NHCs, this is an essential tool for every academic and industrial synthetic chemist.

PrefaceN-HETEROCYCLIC CERBENESIntroductionStructure and Properties of NHCsAbnormal CarbenesWhy Are NHCs Stable?Bonding of NHCs to Metal CentersQuantifying the Properties of NHCsN-Heterocyclic Carbenes in the Context of Other Stable CarbenesSynthesis of NHCsSalts and Adducts of NHCsSummaryTUNING AND QUANTIFYING STERIC AND ELECTRONIC EFFECTS OF N-HETEROCYCLIC CARBENESIntroductionSteric Effects in NHC ligandsElectronic Effects in NHC LigandsConclusionsCHIRAL MONODENDATE N-HETEROCYCLIC CARBENE LIGANDS IN ASYMMETRIC CATALYSISIntroductionNHC-RuNHC-RhNHC-IrNHC-NiNHC-PdNHC-CuNHC-AgNHC-AuConclusion(N-HETEROCYCLIC CARBENE)-PALLADIUM COMPLEXES IN CATALYSISIntroductionCross-Coupling ReactionsChelates and Pincer LigandsAsymmetric CatalysisOxidation ReactionsTelomerization, Oligomerization and PolymerizationAnticancer NHC-Pd ComplexesNHC PLATINUM(0) COMPLEXES: UNIQUE CATALYSTS FOR THE HYDROSILYLATION OF ALKENES AND ALKYNESIntroductionHydrosilylation of Alkenes: The BeginningInitial Results with Phosphine LigandsNHC Platinum(0) Complexes: The BreakthroughHydrosilylation of AlkynesConclusionsSYNTHESIS AND MEDICINAL PROPERTIES OF SILVER-NHC COMPLEXES AND IMIDAZOLIUM SALTSIntroductionSilver-NHC Complexes as Antimicrobial AgentsSilver-NHC Complexes as Anticancer AgentsConclusionsMEDICAL APPLICATIONS OF NHC-GOLD AND -COPPER COMPLEXESIntroductionGold Antimicrobial AgentsMetals as Antitumor ReagentsCopper Complexes as Antitumoral ReagentsConclusionNHC-COPPER COMPLEXES AND THEIR APPLICATIONSIntroductionHistory of NHC-Copper SystemsHydrosilylationAllene Formation1,4-ReductionConjugate AdditionHydrothiolation, Hydroalkoxylation, HydroaminationCarboxylation and Carbonylation (via Boronic Acids, CH Activation): CO2 Insertion[3 + 2] Cycloaddition Reaction: Formation of TriazoleAllylic SubstitutionCarbene and Nitrene TransferBoration ReactionOlefination of Carbonyl DerivativesCopper-Mediated Cross-Coupling ReactionFluoride ChemistryOther ReactionsTransmetalationConclusionNHC-AU(I) COMPLEXES: SYNTHESIS, ACTIVATION, AND APPLICATIONIntroductionSynthesis of NHC-Gold(I) ChloridesActivation of NHC-Au(I) ChloridesApplications of NHC-Au(I) CatalystsConclusionRECENT DEVELOPMENTS IN THE SYNTHESIS AND APPLICATIONS OF RHODIUM AND IRIDIUM COMPLEXES BEARING N-HETEROCYCLIC CARBENE LIGANDSIntroductionRh- and Ir-NHC-Based Complexes: Structural and Electronic Features Mono-NHCsCatalytic Applications of Rhodium and Iridium NHC-Based ComplexesAbbreviationsN-HETEROCYCLIC CARBENE?RUTHNIUM COMPLEXES: A PROMINENT BREAKTHROUGH IN METATHESIS REACTIONSIntroductionVariations of NHC in Ruthenium ComplexesModifications in Imidazol- and Imidazolin-2-ylidene LigandsInfluence of Symmetrically 1,3-Substituted N-Heterocyclic Carbene in MetathesisUnsymmetrically N,N'-Substituted N-Heterocyclic CarbenesRUTHENIUM N-HETEROCYCLIC CARBENE COMPLEXES FOR THE CATALYSIS OF NONMETATHESIS ORGANIC TRANSFORMATIONSIntroductionTransfer HydrogenationDirect Hydrogenation (and Hydrosilylation)Borrowing HydrogenAlcohol RacemizationArylationReactions of AlkynesIsomerization of C=C BondsAllylic Substitution ReactionsMiscellaneous ReactionsConclusionsNICKEL COMPLEXES OF N-HETEROCYCLIC CARBENESIntroductionNickel-NHC CatalystsCross-Coupling ReactionsOxidation/Reduction ReactionsHydrosilylationCycloadditionsIsomerizationReductive CouplingConclusions and OutlookCOODINATION CHEMISTRY, RACTIVITY, AND APPLICATIONS OF EARLY TRANSITION METAL COMPLEXES BEARING N-HETEROCYCLIC CARBENE LIGANDSIntroductionGroup 3 Metal ComplexesGroup 4 Metal ComplexesGroup 5 Metal ComplexesGroup 6 Metal ComplexesGroup 7 Metal ComplexesConclusionNHC COMPLEXES OF MAIN GROUP ELEMNTES: NOVEL STRUCTURES, REACTIVITY, AND CATALYTIC BEHAVIORIntroductionStructures of Common NHCs for Main Group Chemi