Nickel catalysis in organic synthesis: methods and reactions

335 Pages·2020·22.85 MB·English

by  John Wiley & Sons., Ogoshi, Sensuke

NickelCatalysisinOrganicSynthesis
Nickel Catalysis in Organic Synthesis
MethodsandReactions
Editedby
SensukeOgoshi
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v
Contents
Preface xi
PartI ReactionsviaNickelacycles 1
1 FormationofNickelacyclesandReactionwithCarbon
Monoxide 3
SensukeOgoshi
1.1 Introduction 3
1.2 FormationofHetero-nickelacyclesfromNickel(0) 3
1.3 StoichiometricReactionofHetero-nickelacycleswithCarbon
Monoxide 4
References 9
2 TransformationofAldehydesviaNickelacycles 13
YoichiHoshimoto
2.1 IntroductionandScopeofThisChapter 13
2.2 CatalyticTransformationofAldehydesThroughThree-Membered
OxanickelacycleComplexes 14
2.3 CatalyticTransformationofAldehydesThroughFive-Membered
OxanickelacycleComplexes 18
2.4 CatalyticTransformationofAldehydesThroughSeven-Membered
OxanickelacycleComplexes 22
2.5 ConclusionandOutlook 23
References 25
3 TransformationofIminesviaNickelacycles 29
MasatoOhashi
3.1 Introduction 29
3.2 [2+2+1]CarbonylativeCycloadditionofanImineandEitheran
AlkyneoranAlkeneLeadingtoγ-Lactams 29
3.3 [2+2+2]CycloadditionReactionofanIminewithTwoAlkynes:
Formationof1,2-DihydropyridineDerivatives 31
vi Contents
3.4 Three-ComponentCouplingandCyclocondensationReactionsofan
Imine,anAlkyne,andAlkylmetalReagents 34
References 37
4 AsymmetricC—CBondFormationReactionsvia
Nickelacycles 39
RavindraKumarandSensukeOgoshi
4.1 Introduction 39
4.2 EnantioselectiveReactionsInvolvingNickelacycles 39
4.2.1 Nickel-CatalyzedAsymmetricCouplingofAlkynesand
Aldehydes 39
4.2.1.1 Nickel-CatalyzedAsymmetricReductiveCouplingofAlkynesand
Aldehydes 40
4.2.1.2 Nickel-CatalyzedAsymmetricAlkylativeCouplingofAlkynesand
Aldehydes 43
4.2.2 Nickel-CatalyzedAsymmetricCouplingofAlkynesandImines 44
4.2.3 Nickel-CatalyzedAsymmetricCouplingof1,3-Enynesand
Aldehydes 45
4.2.4 Nickel-CatalyzedAsymmetricCouplingof1,3-Enynesand
Ketones 46
4.2.5 Nickel-CatalyzedAsymmetricCouplingof1,3-Dienesand
Aldehydes 47
4.2.6 Nickel-CatalyzedAsymmetricCouplingofEnonesandAlkynes 50
4.2.6.1 Nickel-CatalyzedAsymmetricAlkylativeCouplingofEnonesand
Alkynes 50
4.2.6.2 Nickel-CatalyzedAsymmetricCouplingofEnonesandAlkynes 51
4.2.7 Nickel-CatalyzedAsymmetricCouplingofArylenoatesand
Alkynes 55
4.2.8 Nickel-CatalyzedAsymmetricCouplingofDiyneswithKetenes 56
4.2.9 Nickel-CatalyzedAsymmetricCouplingofAllenes,Aldehydes,and
Silanes 57
4.2.10 Nickel-CatalyzedAsymmetricCouplingofAllenesand
Isocyanates 58
4.2.11 Nickel-CatalyzedAsymmetricCouplingofAlkenes,Aldehydes,and
Silanes 59
4.2.12 Nickel-CatalyzedAsymmetricCouplingofFormamideand
Alkene 61
4.2.13 Nickel-CatalyzedAsymmetricCouplingofAlkynesandCyclopropyl
Carboxamide 63
4.3 Miscellaneous 64
4.3.1 Nickel-CatalyzedAsymmetricAnnulationofPyridonesvia
HydroarylationtoAlkenes 64
4.3.2 Nickel-CatalyzedAsymmetricSynthesisofBenzoxasilole 65
4.4 OverviewandFuturePerspective 66
References 67
Contents vii
PartII FunctionalizationofUnreactiveBonds 69
5 RecentAdvancesinNi-CatalyzedChelation-AssistedDirect
FunctionalizationofInertC—HBonds 71
Yan-HuaLiu,FangHu,andBing-FengShi
5.1 Introduction 71
5.2 Ni-CatalyzedFunctionalizationofInertC—HBondsAssistedby
BidentateDirectingGroups 71
5.2.1 Arylation 72
5.2.2 Alkylation 76
5.2.3 Alkenylation 83
5.2.4 Alkynylation 85
5.2.5 OtherC—CBondFormationReactionsDirectedbyBidentate
DirectingGroup 88
5.2.6 C—NBondFormation 89
5.2.7 C–Chalcogen(Chalcogen=O,S,Se)BondFormation 89
5.2.8 C–HalogenBondFormation 92
5.3 Ni-CatalyzedFunctionalizationofInertC—HBondsAssistedby
MonodentateDirectingGroups 94
5.3.1 Alkylation 94
5.3.2 Alkenylation 95
5.3.3 Alkynylation 96
5.3.4 C–CalcogenBondFormation 97
5.4 Summary 98
References 98
6 C—CBondFunctionalization 103
YoshiakiNakao
6.1 Introduction 103
6.2 C—CBondFunctionalizationofThree-MemberedRings 103
6.3 C—CBondFunctionalizationofFour-andFive-Membered
Rings 110
6.4 C—CBondFunctionalizationofLessStrainedMolecules 113
6.5 C—CNBondFunctionalization 115
6.6 SummaryandOutlook 116
References 117
7 C—OBondTransformations 123
MamoruTobisu
7.1 Introduction 123
7.2 C(aryl)—OBondCleavage 124
7.2.1 ArylEsters,Carbamates,andCarbonates 124
7.2.2 ArylEthers 132
7.2.3 Arenols 136
7.3 C(benzyl)—OBondCleavage 138
viii Contents
7.3.1 BenzylEstersandCarbamates 138
7.3.2 BenzylEthers 140
7.4 C(acyl)—OBondCleavage 141
7.5 SummaryandOutlook 144
References 145
PartIII CouplingReactionsviaNi(I)and/orNi(III) 151
8 Photo-AssistedNickel-CatalyzedCross-Coupling
Processes 153
ChristopheLévêque,CyrilOllivier,andLouisFensterbank
8.1 Introduction 153
8.2 DevelopmentofVisible-LightPhotoredox/NickelDualCatalysis 154
8.2.1 FortheFormationofCarbon–CarbonBonds 154
8.2.1.1 StartingfromOrganotrifluoroborates 154
8.2.1.2 StartingfromCarboxylatesorKetoAcidsorfromMethylanilines 157
8.2.1.3 StartingfromAlkylsilicates 160
8.2.1.4 Startingfrom1,4-Dihydropyridines 166
8.2.1.5 StartingfromAlkylsulfinates 168
8.2.1.6 StartingfromAlkylBromides 168
8.2.1.7 StartingfromXanthates 169
8.2.1.8 StartingfromSp3CHBonds 169
8.2.2 FortheFormationofCarbon–HeteroatomBonds 170
8.2.2.1 FormationofC—OBond 170
8.2.2.2 FormationofC—PBond 171
8.2.2.3 FormationofC—SBond 171
8.3 Energy-Transfer-MediatedNickelCatalysis 173
8.4 Conclusion 175
References 176
9 Cross-ElectrophileCoupling:PrinciplesandNew
Reactions 183
MatthewM.Goldfogel,LiangbinHuang,andDanielJ.Weix
9.1 Introduction 183
9.2 MechanisticDiscussionofCross-ElectrophileCoupling 185
9.3 C(sp2)—C(sp3)BondFormation 188
9.3.1 Cross-ElectrophileCouplingofAryl-XandAlkyl-X 188
9.3.2 Cross-ElectrophileCouplingofArXandBn-X 195
9.3.3 Cross-ElectrophileCouplingofArXandAllyl-X 196
9.3.4 Vinyl-XwithR-X 197
9.3.5 Acyl-XwithAlkyl-X 199
9.4 C(sp2)–C(sp2)Coupling 201
9.4.1 Aryl-X/Vinyl-X+Aryl-X/Vinyl-X 201
9.4.2 Aryl-X+Acyl-X 202
9.5 C(sp3)–C(sp3)Coupling 203
Contents ix
9.6 C(sp)–C(sp3)Coupling 205
9.7 MulticomponentReactions 206
9.8 FutureoftheField 208
References 209
10 OrganometallicChemistryofHigh-ValentNi(III)andNi(IV)
Complexes 223
LiviuM.Mirica,SofiaM.Smith,andLeonelGriego
10.1 Introduction 223
10.2 OrganometallicNi(III)Complexes 223
10.3 OrganometallicNi(IV)Complexes 234
10.4 OtherHigh-ValentNiComplexes 239
10.4.1 AdditionalNiIIIComplexes 239
10.4.2 AdditionalNiIVComplexes 241
10.5 ConclusionsandOutlook 243
References 244
PartIV CarbonDioxideFixation 249
11 CarbonDioxideFixationviaNickelacycle 251
RyoheiDoiandYoshihiroSato
11.1 Introduction:CarbonDioxideasaC1BuildingBlock 251
11.2 Formation,Structure,andReactivityofNickelalactone 252
11.2.1 FormationandCharacterizationofNickelalactoneviaOxidative
CyclizationwithCO 252
2
11.2.1.1 ReactionwithAlkene 252
11.2.1.2 ReactionwithAllene 255
11.2.1.3 ReactionwithDiene 256
11.2.1.4 ReactionwithAlkyne 257
11.2.1.5 OtherRelatedReactions 260
11.2.1.6 GenerationofNickelalactoneWithoutCO 261
2
11.2.2 ReactivityofNickelalactone 261
11.2.2.1 TransmetalationwithOrganometallicReagent 261
11.2.2.2 β-HydrideElimination 263
11.2.2.3 InsertionofAnotherUnsaturatedMolecule 264
11.2.2.4 Retro-cyclization 265
11.2.2.5 NucleophilicAttack 265
11.2.2.6 Oxidation 267
11.2.2.7 LigandExchange 267
11.3 CatalyticTransformationviaNickelalactone1:Reactionsof
Alkynes 268
11.3.1 SynthesisofPyrone 268
11.3.1.1 InitialFinding 268
11.3.1.2 ReactionofDiyneswithCO 268
2
11.3.2 Synthesisofα,β-UnsaturatedEster 269
x Contents
11.3.2.1 ElectrochemicalReactions 269
11.3.2.2 ReductionwithOrganometallicReagents 270
11.4 CatalyticTransformationviaNickelalactone2:ReactionsofAlkenes
andRelatedMolecules 271
11.4.1 TransformationofDiene,Allene,andSubstitutedAlkene 271
11.4.1.1 CouplingofDienewithCO 271
2
11.4.1.2 ElectrochemicalProcess 272
11.4.1.3 UseofReductant 272
11.4.2 SynthesisofAcrylicAcidfromEthyleneandCO 274
2
11.4.2.1 BeforetheDawn 275
11.4.2.2 DevelopmentofCatalyticReaction 276
11.5 ConcludingRemarks 278
References 279
12 RelevanceofNi(I)inCatalyticCarboxylationReactions 285
RosieJ.SomervilleandRubenMartin
12.1 Introduction 285
12.2 MechanisticBuildingBlocks 287
12.2.1 Additives 287
12.2.2 CoordinationofCO 287
2
12.2.3 Insertion/C—CBondFormation 288
12.2.4 LigandEffects 289
12.2.5 OxidativeAddition 290
12.2.6 OxidationState 290
12.2.7 SingleElectronTransfer(SET) 290
12.2.8 Conclusion 290
12.3 Electrocarboxylation 291
12.3.1 Introduction 291
12.3.2 PhosphineLigands 294
12.3.3 BipyridineandRelatedα-DiimineLigands 296
12.3.4 SalenLigands 297
12.3.5 Conclusion 298
12.4 Non-electrochemicalMethods 298
12.4.1 ArylHalides 300
12.4.2 BenzylElectrophiles 304
12.4.3 CarboxylationofUnactivatedAlkylElectrophiles 306
12.4.4 CarboxylationofAllylElectrophiles 312
12.4.5 UnsaturatedSystems 315
12.5 Conclusions 318
References 319
Index 331