Pincer and Pincer-Type Complexes Applications in Organic Synthesis and Catalysis PDF
Preview Pincer and Pincer-Type Complexes Applications in Organic Synthesis and Catalysis
Editedby Ka´lma´nJ.Szabo´and OlaF.Wendt PincerandPincer-TypeComplexes RelatedTitles Nolan,S.P.(ed.) Andersson,P.G.(ed.) N-Heterocyclic InnovativeCatalysisinOrganic Carbenes-EffectiveToolsfor Synthesis Organometallic Synthesis Oxidation,Hydrogenation,andC-XBond FormingReactions 2014 PrintISBN:978-3-527-33490-2,alsoavailablein 2012 digitalformats PrintISBN:978-3-527-33097-3,alsoavailablein digitalformats deMeijere,A.,Bräse,S.,Oestreich,M. (eds.) Kuhl,O. Metal-Catalyzed Cross-Coupling Functionalised N-Heterocyclic ReactionsandMore CarbeneComplexes 2014 2010 PrintISBN:978-3-527-33154-3,alsoavailablein PrintISBN:978-0-470-71215-3,alsoavailablein digitalformats digitalformats Molna´r,A´.(ed.) Palladium-Catalyzed Coupling Reactions 2013 PrintISBN978-3-527-33254-0,alsoavailablein digitalformats Edited by Ka´lma´n J. Szabo´ and Ola F. Wendt Pincer and Pincer-Type Complexes Applications in Organic Synthesis and Catalysis TheEditors AllbookspublishedbyWiley-VCHare carefullyproduced.Nevertheless,authors, editors,andpublisherdonotwarrantthe Prof.Ka´lma´nJ.Szabo´ informationcontainedinthesebooks, StockholmUniversity includingthisbook,tobefreeoferrors. ArrheniusLaboratory Readersareadvisedtokeepinmindthat 10691Stockholm statements,data,illustrations,procedural Sweden detailsorotheritemsmayinadvertentlybe inaccurate. Prof.OlaF.Wendt LundUniversity LibraryofCongressCardNo.:appliedfor OrganicChemistry 22100Lund Sweden BritishLibraryCataloguing-in-Publication Data Acataloguerecordforthisbookisavailable fromtheBritishLibrary. Bibliographicinformationpublishedbythe DeutscheNationalbibliothek TheDeutscheNationalbibliothek liststhispublicationintheDeutsche Nationalbibliografie;detailedbibliographic dataareavailableontheInternetat <http://dnb.d-nb.de>. (cid:2)c 2014Wiley-VCHVerlagGmbH&Co. KGaA,Boschstr.12,69469Weinheim, Germany Allrightsreserved(includingthoseof translationintootherlanguages).Nopart ofthisbookmaybereproducedinany form–byphotoprinting,microfilm,orany othermeans–nortransmittedortranslated intoamachinelanguagewithoutwritten permissionfromthepublishers.Registered names,trademarks,etc.usedinthisbook, evenwhennotspecificallymarkedassuch, arenottobeconsideredunprotectedbylaw. PrintISBN:978-3-527-33442-1 ePDFISBN:978-3-527-68132-7 ePubISBN:978-3-527-68133-4 MobiISBN:978-3-527-68131-0 oBookISBN:978-3-527-68130-3 Cover-Design Grafik-DesignSchulz, Fußgo¨nheim,Germany Typesetting LaserwordsPrivateLimited, Chennai,India PrintingandBinding MarkonoPrintMedia PteLtd,Singapore Printedonacid-freepaper V Contents Preface XI ListofContributors XIII 1 CatalysisbyPincerComplexes:SynthesisofEsters,Amides,and Peptides 1 ChidambaramGunanathanandDavidMilstein 1.1 IntroductionandBackground 1 1.2 BondActivationbyMetal–LigandCooperation 3 1.3 SynthesisofEsters 4 1.3.1 SynthesisofEstersfromPrimaryAlcohols 4 1.3.2 SynthesisofCross-EstersfromPrimaryandSecondaryAlcohols 9 1.3.3 SynthesisofEstersbyAcylationofSecondaryAlcoholsUsing Esters 9 1.3.4 SynthesisofPolyestersfromDiols 11 1.4 SynthesisofAmides 15 1.4.1 SynthesisofAmidesfromAlcoholsandAmines 15 1.4.2 SynthesisofAmidesfromEstersandAmines 18 1.4.3 SynthesisofPolyamidesfromDiolsandDiamines 20 1.5 SynthesisofPeptidesfromβ-AminoAlcohols 24 1.6 ConcludingRemarks 26 Acknowledgments 26 References 27 2 TheRoleofRedoxProcessesinReactionsCatalyzedbyNickeland PalladiumComplexeswithAnionicPincerLigands 31 JuanCa´mporaandCristo´balMelero 2.1 Introduction 31 2.2 PincerComplexesofNi,Pd,andPtinOxidationStatesDifferentfrom II 34 2.2.1 ComplexesintheHigherOxidationStates(III,IV) 34 2.2.2 ReducedComplexesofNi,Pd,andPtwithPincerLigands 43 2.3 CatalyticReactionsInvolvingRedoxProcessesinthePincer-Metal Framework 46 VI Contents 2.3.1 Atom-TransferRadicalAddition(ATRA)andPolymerization Reactions(ATRP) 46 2.3.2 TheHeckReaction 48 2.3.3 C–CCross-CouplingReactions 54 2.3.4 Carbon–HeteroatomCouplingReactions 62 2.4 ConcludingRemarks 65 Acknowledgment 66 References 66 3 AppendedFunctionalityinPincerLigands 71 CameronM.MooreandNathanielK.Szymczak 3.1 Introduction 71 3.1.1 DesignCriteria 72 3.1.2 Motivations 72 3.1.2.1 Transition-MetalCatalysis 72 3.1.2.2 SupramolecularArchitectures 73 3.2 AppendedFunctionalityCoplanarwiththePincerChelate 75 3.2.1 SystemsthatIncorporate2,2′:6′,2′′-Terpyridine 75 3.2.1.1 SyntheticStrategies 75 3.2.1.2 AppendedLewisAcid/Bases 77 3.2.1.3 AppendedHydrogen-BondAcceptor/Donors 79 3.2.2 Pyridine-2,6-DicarboxamideSystems 84 3.3 AppendedFunctionalityNotCoplanartothePincerChelate 86 3.3.1 ENEPincerSystems 86 3.3.2 PCPPincerSystems 88 3.3.3 PEPPincerSystems 88 3.3.4 Pyridine-2,6-DiimineSystems 90 3.4 FutureOutlookandSummary 91 References 91 4 C–C,C–O,andC–BBondFormationbyPincerComplexesIncluding AsymmetricCatalysis 95 Ka´lma´nJ.Szabo´ 4.1 Introduction – ProsandConsofUsingPincerComplexesin Catalysis 95 4.2 ReactionofIminesandIsocyanoacetates 96 4.2.1 StereoselectiveSynthesisofImidazolines 96 4.2.2 ApplicationofChiralPincerComplexes 99 4.2.3 MechanisticConsiderations 101 4.3 C–HFunctionalizationofOrganonitriles 102 4.3.1 AllylationofImines 102 4.3.2 BenzylAmineSynthesis 103 4.4 ReactionsInvolvingHypervalentIodines 107 4.4.1 ArylationofAlkenesUsingPincerComplexCatalysis 107 4.4.2 AcetoxylationwithHypervalentIodines 109 Contents VII 4.4.3 C–HBorylationofAlkenes 112 4.5 SummaryandOutlook 113 References 115 5 Nickel-CatalyzedCross-CouplingReactions 117 AnubenduAdhikaryandHairongGuan 5.1 Introduction 117 5.2 Carbon–CarbonBond-FormingReactions 118 5.2.1 Kumada–Corriu–TamaoCoupling 118 5.2.2 Suzuki–MiyauraCoupling 129 5.2.3 NegishiCoupling 132 5.2.4 SonogashiraCoupling 139 5.2.5 Mizoroki–HeckReaction 140 5.2.6 OtherMiscellaneousCross-CouplingReactions 141 5.3 Carbon–HeteroatomBond-FormingReactions 143 5.4 SummaryandOutlook 144 Acknowledgments 144 References 144 6 PSiPTransition-MetalPincerComplexes:Synthesis,BondActivation, andCatalysis 149 LauraTurculet 6.1 Introduction 149 6.2 PSiPLigandSyntheses 151 6.3 Group8MetalPSiPChemistry 153 6.4 Group9MetalPSiPChemistry 161 6.5 Group10MetalPSiPChemistry 169 6.6 Group11MetalPSiPChemistry 179 6.7 AlternativeSilylPincers 180 6.8 Summary 183 References 183 7 ElectronicStructuresofReducedManganese,Iron,andCobalt ComplexesBearingRedox-ActiveBis(imino)pyridinePincer Ligands 189 PaulJ.Chirik 7.1 Introduction 189 7.2 ReducedManganese,Iron,andCobaltComplexeswithRedox-Active Bis(imino)pyridines 189 7.2.1 ReducedBis(imino)pyridineManganeseChemistry 190 7.2.2 ReducedBis(imino)pyridineIronChemistry 193 7.2.3 ReducedBis(imino)pyridineCobaltChemistry 200 7.3 ConclusionsandOutlook 209 References 209 VIII Contents 8 PincerComplexeswithSaturatedFrameworks:Synthesisand Applications 213 KlaraJ.JonassonandOlaF.Wendt 8.1 Introduction 213 8.2 SynthesisoftheLigands 213 8.3 SynthesisandCoordinationBehaviorofCarbometallatedPC(sp3)P Complexes 215 8.3.1 CoordinationFlexibilityinAcyclicPC(sp3)PComplexes 216 8.4 ReactivityandCatalyticApplicationsofPC(sp3)PComplexes 217 8.4.1 AmmoniaActivation 217 8.4.2 IsotopicLabeling 219 8.4.3 ReactionswithCoordinatedOlefins 219 8.4.4 Carbon–CarbonCouplingReactions 221 8.4.5 HydrogenationandDehydrogenation 223 8.4.6 CO Activation 225 2 References 225 9 HeavierGroup14Elements-BasedPincerComplexesinCatalytic SyntheticTransformationsofUnsaturatedHydrocarbons 229 JunTakayaandNobuharuIwasawa 9.1 Introduction 229 9.2 SynthesisofPalladiumComplexesBearingPXP-PincerLigands (X=Si,Ge,Sn) 230 9.2.1 Synthesis 230 9.2.2 StructuralAnalyses 230 9.3 Hydrocarboxylation 231 9.3.1 HydrocarboxylationofAllenes 232 9.3.2 Hydrocarboxylationof1,3-Dienes 234 9.4 ReductiveAldolTypeReaction 235 9.5 DehydrogenativeBorylation 237 9.5.1 DehydrogenativeBorylationofAlkenesand1,3-Dienes 237 9.5.2 MechanisticConsiderations 239 9.6 SynthesisandReactionofη2-(Si–H)Pd(0)ComplexasanEquivalent toPSiP-PalladiumHydrideComplexes 241 9.6.1 SynthesisandStructureofη2-(Si–H)Pd(0) 241 9.6.2 Reactionofη2-(Si–H)Pd(0)ComplexwithanAllene 242 9.6.3 Reactionofη2-(Si–H)Pd(0)ComplexwithDiboron 244 9.7 Conclusions 245 References 246 10 ExperimentalandTheoreticalAspectsofPalladiumPincer-Catalyzed C–CCross-CouplingReactions 249 ChristianM.Frech 10.1 C–CCross-CouplingReactions – anIndispensableToolforthe SynthesisofComplexOrganicMolecules 249
The list of books you might like
