Non-noble metal catalysis : molecular approaches and reactions

598 Pages·2019·34.544 MB·English

by  Gebbink, Robertus J. M., Moret, Marc-Etienne

Non-NobleMetalCatalysis
Non-Noble Metal Catalysis
MolecularApproachesandReactions
Editedby
RobertusJ.M.KleinGebbink
Marc-EtienneMoret
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10 9 8 7 6 5 4 3 2 1
v
Contents
Preface xvii
1 ApplicationofStimuli-Responsiveand“Non-innocent”Ligands
inBaseMetalCatalysis 1
AndreiChirila,BrajaGopalDas,PetrusF.Kuijpers,VivekSinha,
andBasdeBruin
1.1 Introduction 1
1.2 Stimuli-ResponsiveLigands 2
1.2.1 Redox-ResponsiveLigands 3
1.2.2 pH-ResponsiveLigands 5
1.2.3 Light-ResponsiveLigands 7
1.3 Redox-ActiveLigandsasElectronReservoirs 8
1.3.1 Bis(imino)pyridine(BIP) 8
1.3.1.1 EthylenePolymerizationwithBIP 9
1.3.1.2 CycloadditionReactions 10
1.3.1.3 HydrogenationandHydro-additionReactions 12
1.3.2 OtherLigandsasElectronReservoirs 14
1.4 CooperativeLigands 15
1.4.1 CooperativeReactivitywithLigandRadicals 16
1.4.1.1 GalactoseOxidase(GoAse)anditsModels 16
1.4.1.2 AlcoholOxidationbySalenComplexes 18
1.4.2 BaseMetalCooperativeCatalysiswithLigandsActingas
anInternalBase 18
1.4.2.1 Fe–PincerComplexes 19
1.4.2.2 LigandsContainingaPendantBase 20
1.5 SubstrateRadicalsinCatalysis 21
1.5.1 CarbeneRadicals 22
1.5.2 NitreneRadicals 25
1.6 SummaryandConclusions 26
References 27
2 ComputationalInsightsintoChemicalReactivityandRoad
toCatalystDesign:TheParadigmofCO Hydrogenation 33
2
BhaskarMondal,FrankNeese,andShengfaYe
2.1 Introduction 33
vi Contents
2.1.1 ChemicalReactions:ConceptualThoughts 33
2.1.2 MotivationBehindStudyingCO Hydrogenation 35
2
2.1.3 ChallengesofCO Reduction 35
2
2.1.4 CO Hydrogenation 37
2
2.1.5 NoblevsNon-nobleMetalCatalysis 38
2.1.6 CO Hydrogenation:BasicMechanisticConsiderations 38
2
2.2 ReactionEnergeticsandGoverningFactor 39
2.3 NewlyDesignedCatalystsandTheirReactivity 42
2.4 CorrelationBetweenHydricityandReactivity 43
2.5 ConcludingRemarks 45
Acknowledgments 46
References 47
3 CatalysiswithMultinuclearComplexes 49
NealP.Mankad
3.1 Introduction 49
3.2 StoichiometricReactionPathways 50
3.2.1 BimetallicBindingandActivationofSubstrates 50
3.2.1.1 Small-MoleculeActivation 51
3.2.1.2 AlkyneActivation 52
3.2.2 BimetallicAnalogsofOxidativeAdditionandReductive
Elimination 53
3.2.2.1 E—HAdditionandElimination 54
3.2.2.2 C—XActivationandC—CCoupling 56
3.2.2.3 C=OCleavage 57
3.3 ApplicationinCatalysis 57
3.3.1 CatalysiswithReactiveMetal–MetalBonds 58
3.3.1.1 BimetallicAlkyneCycloadditions 58
3.3.1.2 BimetallicOxidativeAddition/ReductiveEliminationCycling 59
3.3.2 BifunctionalandTandemCatalysiswithoutMetal–Metal
Bonds 59
3.3.2.1 CooperativeActivationofUnsaturatedSubstrates 59
3.3.2.2 CooperativeProcesseswithBimetallicOxidativeAdditionand/or
ReductiveElimination 62
3.4 PolynuclearComplexes 64
3.5 Outlook 65
Acknowledgments 66
References 66
4 Copper-CatalyzedHydrogenationsandAerobicN—NBond
Formations:AcademicDevelopmentsandIndustrial
Relevance 69
PaulL.AlstersandLaurentLefort
4.1 Introduction 69
4.2 Cu-PromotedN—NBondFormation 70
4.2.1 NoncyclizationN—NorN=NBondFormations 71
Contents vii
4.2.1.1 N—NSingle-Bond-FormingReactions 71
4.2.1.2 N=NDoubleBond-FormingReactions 72
4.2.2 CyclizationN—NBondFormations 74
4.2.2.1 DehydrogenativeCyclizations 77
4.2.2.2 EliminativeCyclizations 80
4.2.2.3 EliminativeDehydrogenativeCyclizations 81
4.3 Cu-CatalyzedHomogeneousHydrogenation 82
4.3.1 HydrogenationofCO toFormateandDerivatives 84
2
4.3.2 HydrogenationofCarbonylCompounds 86
4.3.3 HydrogenationofOlefinsandAlkynes 89
4.4 Conclusions 91
References 92
5 C=CHydrogenationswithIronGroupMetalCatalysts 97
TimN.GieshoffandAxelJ.vonWangelin
5.1 Introduction 97
5.2 Iron 99
5.2.1 Introduction 99
5.2.2 PincerComplexes 100
5.2.3 Others 106
5.3 Cobalt 107
5.3.1 Introduction 107
5.3.2 PincerComplexes 108
5.3.3 Others 115
5.4 Nickel 118
5.4.1 Introduction 118
5.4.2 PincerComplexes 119
5.4.3 Others 121
5.5 Conclusion 122
Acknowledgments 123
References 123
6 BaseMetal-CatalyzedAdditionReactionsAcrossC—CMultiple
Bonds 127
RodrigoRamírez-ContrerasandBillMorandi
6.1 Introduction 127
6.2 CatalyticAdditiontoAlkenesInitiatedThroughRadical
Mechanisms 128
6.2.1 HydrogenAtomTransferasaGeneralApproachto
HydrofunctionalizationofUnsaturatedBonds 128
6.2.2 HydrazinesandAzidesviaHydrohydrazinationand
HydroazidationofOlefins 128
6.2.2.1 Co-andMn-CatalyzedHydrohydrazination 128
6.2.2.2 Cobalt-andManganese-CatalyzedHydroazidationofOlefins 130
6.2.3 Co-CatalyzedHydrocyanationofOlefinswithTosylCyanide 133
6.2.4 Co-CatalyzedHydrochlorinationofOlefinswithTosyl
Chloride 133
viii Contents
6.2.5 FeIII/NaBH -MediatedAdditionsofUnactivatedAlkenes 134
4
6.2.6 Co-CatalyzedMarkovnikovHydroalkoxylationofUnactivated
Olefins 135
6.2.7 Fe-CatalyzedHydromethylationofUnactivatedOlefins 137
6.2.8 HydroaminationofOlefinsUsingNitroarenes
toObtainAnilines 137
6.2.9 Dual-CatalyticMarkovnikovHydroarylationofAlkenes 139
6.3 OtherCatalyticAdditionstoUnsaturatedBondsProceeding
ThroughInitialR⋅(R≠H)Attack 139
6.3.1 Cu-CatalyzedTrifluoromethylationofUnactivatedAlkenes 139
6.3.2 Mn-CatalyzedAerobicOxidativeHydroxyazidation
ofAlkenes 139
6.3.3 Fe-CatalyzedAminohydroxylationofAlkenes 141
6.4 CatalyticAdditiontoAlkenesInitiatedThroughPolar
Mechanisms 143
6.4.1 Cu-CatalyzedHydroaminationofAlkenesandAlkynes 143
6.4.2 Ni-Catalyzed,Lewis-acid-AssistedCarbocyanation
ofAlkynes 147
6.4.3 Ni-CatalyzedTransferHydrocyanation 148
6.5 HydrosilylationReactions 150
6.5.1 Fe-Catalyzed,Anti-MarkovnikovHydrosilylationofAlkeneswith
TertiarySilanesandHydrosiloxanes 150
6.5.2 HighlyChemoselectiveCo-CatalyzedHydrosilylationof
FunctionalizedAlkenesUsingTertiarySilanesand
Hydrosiloxanes 151
6.5.3 AlkeneHydrosilylationUsingTertiarySilaneswithα-DiimineNi
Catalysts 151
6.5.4 ChemoselectiveAlkeneHydrosilylationCatalyzedbyNiPincer
Complexes 154
6.5.5 Fe-andCo-CatalyzedRegiodivergentHydrosilylation
ofAlkenes 155
6.5.6 Co-CatalyzedMarkovnikovHydrosilylationofTerminalAlkynesand
Hydroborylationofα-Vinylsilanes 155
6.5.7 FeandCoPivalateIsocyanide-LigatedCatalystSystemsfor
HydrosilylationofAlkeneswithHydrosiloxanes 157
6.6 Conclusion 159
References 160
7 Iron-CatalyzedCyclopropanationofAlkenesbyCarbene
TransferReactions 163
DanielaIntrieri,DanielaM.Carminati,andEmmaGallo
7.1 Introduction 163
7.2 AchiralIronPorphyrinCatalysts 165
7.3 ChiralIronPorphyrinCatalysts 172
7.4 IronPhthalocyaninesandCorroles 176
7.5 IronCatalystswithNorN,OLigands 180
7.6 The[Cp(CO) FeII(THF)]BF Catalyst 184
2 4
Contents ix
7.7 Conclusions 186
References 187
8 NovelSubstratesandNucleophilesinAsymmetric
Copper-CatalyzedConjugateAdditionReactions 191
RavindraP.Jumde,SyuzannaR.Harutyunyan,andAdriaanJ.Minnaard
8.1 Introduction 191
8.2 CatalyticAsymmetricConjugateAdditionstoα-Substituted
α,β-UnsaturatedCarbonylCompounds 192
8.3 CatalyticAsymmetricConjugateAdditionsto
Alkenyl-heteroarenes 196
8.3.1 ABriefOverviewofAsymmetricNucleophilicConjugate
AdditionstoAlkenyl-heteroarenes 197
8.3.2 Copper-CatalyzedAsymmetricNucleophilicConjugate
AdditionstoAlkenyl-heteroarenes 198
8.4 Conclusion 205
References 207
9 AsymmetricReductionofPolarDoubleBonds 209
RaphaelBigler,LorenaDeLuca,RaffaelHuber,andAntonioMezzetti
9.1 Introduction 209
9.1.1 CatalyticApproachesforPolarDoubleBondReduction 209
9.1.2 TheRoleofHydrideComplexes 210
9.1.3 LigandChoiceandCatalystStability 211
9.2 Manganese 211
9.3 Iron 212
9.3.1 IronCatalystsinAsymmetricTransferHydrogenation(ATH) 213
9.3.2 IronCatalystsinAsymmetricDirect(H )Hydrogenation(AH) 218
2
9.3.3 IronCatalystsinAsymmetricHydrosilylation(AHS) 220
9.4 Cobalt 223
9.4.1 CobaltCatalystsintheAHofKetones 223
9.4.2 CobaltCatalystsintheATHofKetones 224
9.4.3 CobaltCatalystsinAsymmetricHydrosilylation 225
9.4.4 AsymmetricBorohydrideReductionandHydroboration 226
9.5 Nickel 228
9.5.1 NickelCatalystsinAsymmetricH Hydrogenation 228
2
9.5.2 NickelATHCatalysts 228
9.5.3 NickelAHSCatalysts 229
9.5.4 Nickel-CatalyzedAsymmetricBorohydrideReduction 230
9.5.5 Ni-CatalyzedAsymmetricHydroborationofα,β-Unsaturated
Ketones 230
9.6 Copper 231
9.6.1 Copper-CatalyzedAH 231
9.6.2 Copper-CatalyzedATHofα-Ketoesters 232
9.6.3 Copper-CatalyzedAHSofKetonesandImines 232
9.7 Conclusion 235
References 235
x Contents
10 Iron-,Cobalt-,andManganese-CatalyzedHydrosilylationof
CarbonylCompoundsandCarbonDioxide 241
ChristopheDarcel,Jean-BaptisteSortais,DuoWei,and
AntoineBruneau-Voisine
10.1 Introduction 241
10.2 HydrosilylationofAldehydesandKetones 241
10.2.1 Iron-CatalyzedHydrosilylation 242
10.2.2 Cobalt-CatalyzedHydrosilylation 247
10.2.3 Manganese-CatalyzedHydrosilylation 248
10.3 ReductionofIminesandReductiveAminationofCarbonyl
Compounds 251
10.4 ReductionofCarboxylicAcidDerivatives 252
10.4.1 CarboxamidesandUreas 252
10.4.2 CarboxylicEsters 254
10.4.3 CarboxylicAcids 257
10.5 HydroelementationofCarbonDioxide 258
10.5.1 HydrosilylationofCarbonDioxide 258
10.5.2 HydroborationofCarbonDioxide 259
10.6 Conclusion 260
References 261
11 ReactiveIntermediatesandMechanisminIron-Catalyzed
Cross-coupling 265
JaredL.Kneebone,JeffreyD.Sears,andMichaelL.Neidig
11.1 Introduction 265
11.2 Cross-couplingCatalyzedbySimpleIronSalts 266
11.2.1 MethodsOverview 266
11.2.2 MechanisticInvestigations 267
11.3 TMEDAinIron-CatalyzedCross-coupling 273
11.3.1 MethodsOverview 273
11.3.2 MechanisticInvestigations 275
11.4 NHCsinIron-CatalyzedCross-coupling 276
11.4.1 MethodsOverview 276
11.4.2 MechanisticInvestigations 279
11.5 PhosphinesinIron-CatalyzedCross-coupling 283
11.5.1 MethodsOverview 283
11.5.2 MechanisticInvestigations 285
11.6 FutureOutlook 291
Acknowledgments 291
References 291
12 RecentAdvancesinCobalt-CatalyzedCross-coupling
Reactions 297
OriolPlanas,ChristopherJ.Whiteoak,andXaviRibas
12.1 Introduction 297
12.2 Cobalt-CatalyzedC—CCouplingsThroughaC—HActivation
Approach 299
Contents xi
12.2.1 Low-ValentCobaltCatalysis 299
12.2.2 High-ValentCobaltCatalysis 302
12.3 Cobalt-CatalyzedC—CCouplingsUsingaPreactivatedSubstrate
Approach(ArylHalidesandPseudohalides) 308
12.3.1 ArylorAlkenylHalides,C(sp2)–X 308
12.3.2 AlkylHalides,C(sp3)–X 309
12.3.3 AlkynylHalides,C(sp)–X 311
12.3.4 ArylHalidesWithoutOrganomagnesium 311
12.4 Cobalt-CatalyzedC—XCouplingsUsingC—HActivation
Approaches 312
12.4.1 C—NBondFormation 313
12.4.2 C—OandC—SBondFormation 317
12.4.3 C—XBondFormation(X=Cl,Br,I,andCN) 318
12.5 Cobalt-CatalyzedC—XCouplingsUsingaPreactivatedSubstrate
Approach(ArylHalidesandPseudohalides) 320
12.5.1 C(sp2)–SCoupling 320
12.5.2 C(sp2)–NCoupling 321
12.5.3 C(sp2)–OCoupling 322
12.6 Miscellaneous 322
12.7 ConclusionsandFutureProspects 323
Acknowledgments 323
References 324
13 TrifluoromethylationandRelatedReactions 329
JérémyJacquet,LouisFensterbank,andMarineDesage-ElMurr
13.1 TrifluoromethylationReactions 329
13.1.1 Copper(I)SaltswithNucleophilicTrifluoromethylSources 329
13.1.1.1 ReactionswithElectrophiles 330
13.1.1.2 ReactionswithNucleophiles:OxidativeCoupling 331
13.1.2 GenerationofCF •RadicalsUsingLanglois’Reagent 332
3
13.1.3 CopperandElectrophilicCF +Sources 333
3
13.2 TrifluoromethylthiolationReactions 341
13.2.1 NucleophilicTrifluoromethylthiolation 342
13.2.1.1 Copper-CatalyzedNucleophilicTrifluoromethylthiolation 342
13.2.1.2 Nickel-CatalyzedNucleophilicTrifluoromethylthiolation 344
13.2.2 ElectrophilicTrifluoromethylthiolation 345
13.3 PerfluoroalkylationReactions 348
13.4 Conclusion 350
References 350
14 CatalyticOxygenationofC=CandC—HBonds 355
PradipGhosh,Marc-EtienneMoret,andRobertJ.M.KleinGebbink
14.1 Introduction 355
14.2 OxygenationofC=CBonds 356
14.2.1 ManganeseCatalysts 356
14.2.2 IronCatalysts 363
14.2.3 Cobalt,Nickel,andCopperCatalysts 372