Supramolecular Catalysis: New Directions and Developments

695 Pages·2022·34.113 MB·English

by  Piet W.N.M. van Leeuwen, Matthieu Raynal

SupramolecularCatalysis

Supramolecular Catalysis
New Directions and Developments
Edited by Piet W.N.M. van Leeuwen and Matthieu Raynal
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10 9 8 7 6 5 4 3 2 1
v
Contents
Preface xix
SupramolecularCatalysis:AnIntroduction xxi
PartI Ligand–LigandInteractions 1
1 SupramolecularConstructionofBidentateLigandsThrough
Self-assemblybyHydrogenBonding 3
FelixBauerandBernhardBreit
1.1 Introduction 3
1.2 FormationofBidentateLigandsThroughSelf-assemblyviaHydrogen
BondingandApplicationinHydroformylation 5
1.2.1 2-Hydroxypyridine/2-PyridonePlatform 5
1.2.2 ComplementaryHydrogenBondingfortheConstructionof
HeterodimericSelf-assemblingLigands 9
1.3 AsymmetricHydrogenation 13
1.3.1 P-chiralSelf-assemblyLigandsinAsymmetricHydrogenation 13
1.3.2 InducingAxialChiralityinaSupramolecularCatalyst 14
1.4 OtherCatalyticApplications 17
1.4.1 HydrationofAlkynes 17
1.4.2 HydrationofNitriles 19
1.4.3 AllylicSubstitutionwithAllylicAlcohols 20
1.4.4 Hydrocyanation 20
1.5 ConcludingRemarks 21
References 22
2 Self-AssembledBidentateLigandsinTransitionMetal
Catalysis;FromFundamentalInventiontoCommercial
Application 27
AlexanderM.Kluwer,XavierCaumes,andJoostN.H.Reek
2.1 Introduction 27
2.2 Metal–LigandInteractions,theSUPRAphosLibrary 28
vi Contents
2.3 SupramolecularBidentateLigandsBasedonHydrogenBonds,a
ToolboxforEvolutionaryCatalystDesign 30
2.4 FormationofSupramolecularPincer-TypeComplexes 34
2.5 FromaSupramolecularBidentateLigandtoaCatalystwith
SubstratePre-organization 36
2.6 Outlook 37
References 38
PartII Self-AssembledNanostructuresand
Multi-componentAssemblies 41
3 AssembledIonicMolecularCatalystsandLigands 43
KohsukeOhmatsu,DaisukeUraguchi,andTakashiOoi
3.1 Introduction 43
3.2 ConceptofIon-PairedChiralLigand 44
3.2.1 DesignandSynthesisofIon-PairedChiralLigand 45
3.2.2 ApplicationofIon-PairedChiralLigandforPalladium-Catalyzed
AsymmetricAllylations 45
3.2.3 InsituGenerationofIon-PairedChiralLigandsandTheir
CombinatorialScreening 46
3.3 Hydrogen-Bond-AssistedIon-PairingforSupramolecule
Formation 47
3.3.1 DiscoveryofSupramolecularIon-PairCatalysis 48
3.3.2 SupramolecularIon-PairCatalysisforMichaelAdditionof
2-UnsubstitutedAzlactonetoNitroolefins 50
3.4 Conclusion 51
References 51
4 Self-amplificationofEnantioselectivityinAsymmetric
CatalysisbySupramolecularRecognitionand
Stereodynamics 55
OliverTrapp
4.1 Introduction 55
4.2 DesignofanEnantioselectiveSelf-amplifyingCatalystBasedon
NoncovalentProduct–CatalystInteractions 57
4.3 TheStereodynamicsoftheLigandCore 57
4.4 DesignofProduct–CatalystAdductsandCatalystSynthesis 59
4.5 NoncovalentInteractionStudiesviaNMRSpectroscopy 61
4.6 Self-amplifyingHydrogenationof3,5-DNB-ΔAla-OEt 63
4.7 ConcludingRemarks 64
Acknowledgments 64
References 64
Contents vii
5 InterlockedMoleculesinEnantioselectiveCatalysis 69
CarelKwamenandJochenNiemeyer
5.1 Introduction 69
5.2 RotaxanesinEnantioselectiveCatalysis 70
5.3 CatenanesinEnantioselectiveCatalysis 75
5.4 MolecularKnotsinEnantioselectiveCatalysis 77
5.5 Conclusion 78
References 78
6 CatalyticSupramolecularGels 81
BeatriuEscuder
6.1 Introduction 81
6.2 CatalyticLMWGs 82
6.3 LMWGsinOrganocatalysis 82
6.4 LMWGsinMetallocatalysis 86
6.5 MulticomponentSupramolecularMaterialsInvolvingCatalytic
LMWGs 87
6.6 ConcludingRemarks 89
Acknowledgments 90
References 90
7 SupramolecularHelicalCatalysts 93
LaurentBouteillerandMatthieuRaynal
7.1 Introduction 93
7.2 Concept:InductionofChiralitytoMetalCentersConnectedto
SupramolecularHelices 94
7.3 AmplificationofChiralityinTwo-ComponentSupramolecular
HelicalCatalysts 97
7.4 AmplificationofChiralityinThree-ComponentHelical
Catalysts 98
7.5 SwitchableAsymmetricCatalysisbyReversibleAssemblyofHelical
Catalysts 100
7.6 DualStereocontrolofanAsymmetricReactionbySwitchable
HelicalCatalysts 101
7.7 ConcludingRemarks 103
Acknowledgments 104
References 104
8 Self-AssembledMulti-ComponentSupramolecularCatalysts
forAsymmetricReactions 107
GuanghuiOuyang,JianJiang,andMinghuaLiu
References 114
viii Contents
PartIII Ligand–SubstrateInteractions 117
9 HarnessingLigand–SubstrateNon-covalentInteractionsfor
ControlofSite-SelectivityinTransitionMetal-CatalyzedC–H
ActivationandCross-Coupling 119
RobertJ.Phipps
9.1 Introduction 119
9.2 C–HBorylation 120
9.3 Cross-Coupling 126
9.4 ConcludingRemarks 128
Acknowledgments 129
References 129
10 SupramolecularInteractionsinDistalC–HActivationof
(Hetero)arenes 133
JyotiP.BiswasandDebabrataMaiti
10.1 Introduction 133
10.2 DistalC–HActivationofArenes 133
10.2.1 metaC–HActivation 134
10.2.2 paraC–HActivation 136
10.3 DistalC–HActivationofHeterocycles 137
10.3.1 TridentateApproach 138
10.3.2 BidentateApproach 140
10.4 Conclusion 141
Acknowledgments 141
References 141
11 Transition-Metal-Catalyzed,Site-andEnantioselective
OxygenandNitrogenTransferEnabledbyLactamHydrogen
Bonds 145
FinnBurgandThorstenBach
11.1 ChiralLactamsasHydrogenBondingSitesforEnantioselective
Catalysis 145
11.2 EnantioselectiveAdditiontoOlefins 147
11.3 EnantioselectiveC(sp3)–HFunctionalization 150
11.4 EnantioselectiveOxidationofSulfurCenters 156
11.5 ConcludingRemarks 157
Acknowledgments 158
References 158
12 SupramolecularSubstrateOrientationasStrategytoControl
SelectivityinTransitionMetalCatalysis 161
JoostN.H.ReekandBasdeBruin
12.1 Introduction 161
12.2 AsymmetricHydrogenation 161
Contents ix
12.3 SubstrateOrientationinHydroformylationCatalysis 164
12.4 SubstrateOrientationinC—HBorylation 168
12.5 SecondCoordinationSphereControlinEnantioselective
Cobalt-catalyzedCarbeneandNitreneTransferReactions 170
12.5.1 Applications 172
12.6 ConcludingRemarksandOutlook 174
References 174
13 PhosphineLigandswithAcylguanidiniumGroupsas
Substrate-directingUnit 179
FelixBauerandBernhardBreit
13.1 Introduction 179
13.2 HydroformylationofAlkenoicandAlkynoicAcids 179
13.3 AldehydeReductionandTandem
Hydroformylation–Hydrogenation 188
13.4 ConcludingRemarks 197
References 198
14 ChemicalReactionsControlledByRemoteZn···NInteractions
BetweenSubstratesandCatalysts 201
JonathanTrouvéandRafaelGramage-Doria
14.1 Introduction 201
14.2 OrganicReactions 202
14.3 TransitionMetalCatalysis 204
14.4 Conclusion 207
Acknowledgments 207
References 207
PartIV CatalysisPromotedbyDiscreteCages,Capsules,
andOtherConfinedEnvironments 211
15 ArtificialEnzymesCreatedThroughMolecularImprinting
ofCross-LinkedMicelles 213
YanZhao
15.1 Introduction 213
15.2 Surface-Cross-LinkedMicelles(SCMs) 213
15.3 MolecularlyImprintedNanoparticles(MINPs)viaDouble
Cross-LinkingofMicelles 215
15.4 MINP-BasedArtificialEsterase 217
15.5 MINP-BasedArtificialGlycosidase 219
15.6 MINP-BasedArtificialEnzymesforAsymmetricCatalysisand
TandemCatalysis 223
15.7 ConcludingRemarks 225
Acknowledgments 226
References 226