Metal Catalyzed Cross-Coupling Reactions and More

1543 Pages·2014·14.743 MB·English

by  Armin de Meijere (editor), Stefan Bräse (editor), Martin Oestreich (editor)

Editedby
ArmindeMeijere,StefanBra¨se,and
MartinOestreich
Metal-CatalyzedCross-CouplingReactions
andMore
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Edited by Armin de Meijere, Stefan Bra¨se, and
Martin Oestreich
Metal-Catalyzed Cross-Coupling Reactions
and More
Volume 1
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V
ContentstoVolume 1
Preface XV
ListofContributors XVII
1 MechanisticAspectsofMetal-CatalyzedC,C-andC,X-BondForming
Reactions 1
AntonioM.EchavarrenandAnnaHoms
1.1 MechanismsofCross-CouplingReactions 1
1.1.1 TheEarlierMechanisticProposal:TheStilleReaction 2
1.1.2 TheOxidativeAddition 3
1.1.2.1 Cis-ComplexesintheOxidativeAddition 4
1.1.2.2 TheRoleofAlkeneandAnionicLigands 5
1.1.2.3 Cross-CouplingsinthePresenceofBulkyPhosphines 6
1.1.2.4 N-HeterocyclicCarbenesasLigands 12
1.1.2.5 PalladacyclesasCatalysts 13
1.1.2.6 InvolvementofPd(IV)inCatalyticCycles 14
1.1.2.7 OxidativeAdditionofStannanestoPd(0) 16
1.1.3 TheTransmetallationintheStilleReaction 16
1.1.3.1 IsolationoftheTransmetallationStep 16
1.1.3.2 DissociativeMechanisticProposals 18
1.1.3.3 CyclicandOpenAssociativeTransmetallation 19
1.1.3.4 TheCopperEffect 23
1.1.3.5 TransmetallationintheSuzuki–MiyauraReaction 24
1.1.3.6 TransmetallationintheNegishiReaction 27
1.1.3.7 TransmetallationintheHiyamaReaction 28
1.1.3.8 CouplingsCatalyzedbyCopperandGold 30
1.1.3.9 CouplingsCatalyzedbyIronandCobalt 32
1.1.4 ReductiveElimination 33
1.2 Palladium-Catalyzedα-ArylationofCarbonylCompoundsand
Nitriles 35
1.3 FormationofC–X(X=N,O,S)BondsinMetal-Catalyzed
Reactions 36
VI Contents
1.3.1 ReductiveEliminationtoGenerateC–N,C–O,andC–SBondsfrom
Organopalladium(II)Complexes 39
1.3.2 Nickel-andCopper-CatalyzedFormationofC–XBonds 44
1.4 SummaryandOutlook 46
ListofAbbreviations 46
References 47
2 State-of-the-ArtinMetal-CatalyzedCross-CouplingReactionsof
OrganoboronCompoundswithOrganicElectrophiles 65
JackC.H.LeeandDennisG.Hall
2.1 Introduction 66
2.1.1 CatalyticCycle 66
2.1.2 ImprovementstowardMoreEfficientCross-CouplingConditions 69
2.1.2.1 DevelopmentofNewPhosphineandNHCLigands 69
2.1.2.2 UsageofMaskedBoronDerivativesasCross-CouplingPartners 70
2.1.2.3 LewisAcidsasAdditives 72
2.1.2.4 AdjustingtheNucleophilicityofOrganoboronCross-Coupling
Partners 73
2.1.2.5 CopperSaltsasAdditives 74
2.2 AdvancesinCross-CouplingReactionsfortheFormationof
C(sp2)–C(sp2)Bonds 75
2.2.1 Background 75
2.2.2 RecentDevelopmentsintheUseofNewElectrophilicCoupling
Partners 75
2.2.2.1 Chlorides 75
2.2.2.2 Fluorides 79
2.2.2.3 Pseudohalides 82
2.2.3 RecentDevelopmentsinOrganoboronCross-CouplingPartners 92
2.2.3.1 TrifluoroborateSalts 93
2.2.3.2 N-MethyliminodiaceticAcid(MIDA)Boronates 97
2.2.3.3 OtherOrganoboronCross-CouplingPartners 99
2.2.4 SynthesisofEnantiomericallyEnrichedAtropisomers 101
2.3 AdvancesintheCross-CouplingReactionsfortheFormationof
C(sp3)–C(sp2)orC(sp3)–C(sp3)Bonds 103
2.3.1 Background 103
2.3.1.1 Stereochemistry 104
2.3.2 Cross-CouplingsbetweenUnsaturatedsp2CarbonCentersandsp3
CarbonCenters 105
2.3.2.1 Cross-Couplingsbetweensp3AlkylHalidesandsp2AlkenylorAryl
BoronDerivatives 105
2.3.2.2 Cross-Couplingsbetweensp3AlkylBoronDerivativeswithsp2Alkenyl
orArylHalides 110
2.3.3 Cross-Couplingsbetweensp3CarbonCenterswithsp3Carbon
Centers 117
2.3.3.1 Cross-CouplingsbetweenAchiralSubstrates 117
Contents VII
2.3.3.2 StereoselectiveCross-CouplingReactionsofsp3AlkylHalideswithsp3
Alkylboranes 118
2.4 ExperimentalProcedures 121
2.4.1 2,6-Dimethoxy-2(cid:2),6(cid:2)-dimethylbiphenyl(55) 121
2.4.2 4-Methoxybiphenyl(R=C(O)NEt ,R(cid:2)=H,Ar=
2
4-methoxyphenyl) 121
2.4.3 1-Phenylnaphthalene(ROH=naphthol,Ar=Ph) 122
2.4.4 1-(3,5-Dimethoxyphenyl)-5-phenylpentan-3-one(R -BF K=197,
alkyl 3
R1=CH CH Ph,R(cid:2)=3,5-dimethoxybenzene) 122
2 2
2.4.5 1-Phenyl-1-(4-acetylphenyl-ethane(ArI=4-iodoacetophenone) 122
2.4.6 Naphthalene-1,8-diamido(dan)derivative(Ar=Ph) 123
2.4.7 2-Methyl-5-phenylpentylbenzyl(phenyl)carbamate(R =Me,
alkyl
X=Br,R(cid:2) =CH CH CH Ph) 123
alkyl 2 2 2
2.5 SummaryandOutlook 124
References 124
3 Pd-CatalyzedCross-CouplingwithOrganometalsContainingZn,Al,Zr,
andsoon – TheNegishiCouplingandItsRecentAdvances 133
ShiqingXu,HirofumiKamada,EunHooKim,AkimichiOda,and
Ei-ichiNegishi
3.1 BackgroundandDiscovery 134
3.1.1 WhyMetals?WhyTransitionMetals? 134
3.1.2 WhyTransitionMetal-CatalyzedOrganometallicReactions? 136
3.2 DiscoveryofthePd-orNi-CatalyzedCross-CouplingReactionsof
OrganometalsContainingZn,Al,Zr,andB 137
3.3 TheCurrentScopeofthePd-orNi-CatalyzedCross-couplingandIts
ApplicationtotheSynthesisofNaturalProductsandOtherComplex
OrganicCompounds 154
3.3.1 Cross-CouplingbetweenTwoUnsaturated(Aryl,Alkenyl,and/or
Alkynyl)Groups 156
3.3.1.1 Aryl–ArylCoupling 156
3.3.1.2 Aryl–AlkenylandAlkenyl–ArylCouplings 158
3.3.1.3 Alkenyl–AlkenylCoupling 159
3.3.1.4 Pd-CatalyzedAlkynylation 191
3.3.2 Cross-CouplingInvolvingOneAllyl,Benzyl,orPropargylGroup 197
3.3.2.1 1,4-DienesviaPd-CatalyzedAlkenyl–AllylandAllyl–AlkenylCoupling
and1,4-EnynesbyPd-CatalyzedAlkynyl–AllylCoupling 197
3.3.2.2 Benzyl–Aryl,Aryl–BenzylCoupling 203
3.3.2.3 AllylbenzeneDerivativesviaPd-CatalyzedAlkenyl–BenzylCoupling
andAryl–AllylandAllyl–ArylCoupling 204
3.3.2.4 BenzylatedAlkynesviaPd-CatalyzedAlkynyl–BenzylCouplingand
Aryl–PropargylaswellasPropargyl–ArylCoupling 204
3.3.2.5 1,4-DiynesviaAlkynyl–PropargylCoupling 207
VIII Contents
3.3.2.6 SynthesisofNaturalProductsContaining1,4-DieneandAllylated
ArenesbyPd-CatalyzedAllylation,Benzylation,and
Propargylation 208
3.3.3 Cross-CouplingbetweenTwoAllyl,Benzyl,and/orPropargyl
Groups 210
3.3.3.1 1,5-Dienesand1,5-EnynesviaPd-CatalyzedCross-Couplingswith
Allyl,Benzyl,PropargylElectrophiles 210
3.3.3.2 1,5-Dienesand1,5-EnynesviaPd-CatalyzedHomoallyl–Alkenyl
CouplingandHomopropargyl–AlkenylCoupling 212
3.3.3.3 Bibenzyls,Homoallylarenes,1,5-Dienes,Homopropargylarenes,and
1,5-EnynesviaPd-CatalyzedNegishiCoupling 214
3.3.4 Cross-CouplingInvolvingAlkylmetalsand/orAlkylElectrophiles
OtherThanThoseContainingAllyl,Benzyl,and/orPropargyl
Groups 216
3.3.4.1 Pd-CatalyzedAlkyl–AlkylCoupling 219
3.3.4.2 Ni-CatalyzedAlkyl–AlkylCoupling 221
3.3.4.3 CatalyticAsymmetricCross-CouplingReactionswithSecondaryAlkyl
Halides 223
3.3.5 Pd-CatalyzedAcylation,Cyanation,andα-SubstitutionofEnolatesand
RelatedDerivatives 227
3.3.5.1 Pd-CatalyzedAcylation 227
3.3.5.2 Pd-CatalyzedCyanation 232
3.3.5.3 Pd-Catalyzedα-SubstitutionofEnolatesandRelatedDerivatives 233
3.4 Zr-CatalyzedAsymmetricCarboaluminationofAlkenes(ZACA)
ZACA–Pd-orCu-CatalyzedCross-CouplingSequentialProcessesasa
GeneralRoutetoEnantiomericallyEnrichedChiralOrganic
Compounds 243
3.4.1 Zirconium-CatalyzedAsymmetricCarboaluminationofAlkenes
(ZACAReaction) 243
3.4.1.1 HistoricalandMechanisticBackgroundofCarbometallationof
AlkenesandAlkyneswithAlkylzirconoceneDerivatives 244
3.4.1.2 CatalyticAsymmetricCarbometallationofAlkenesProceedingvia
DzhemilevEthylmagnesiations 246
3.4.2 CurrentSummaryofDevelopmentandApplicationoftheZACA
ReactionandConclusion 249
3.4.2.1 ZACA–Pd-CatalyzedCross-CouplingSequentialProcessesforthe
SynthesisofDeoxypolypropionatesandRelatedCompounds 249
3.4.2.2 ZACA–Lipase-CatalyzedAcetylation–Pd-orCu-Catalyzed
Cross-CouplingSynergytoChiralOrganicCompounds 253
3.5 RepresentativeExperimentalProcedures 260
3.5.1 (2Z,4S)-5-(tert-Butyldimethylsilyloxy)-2-phenyl-4-methyl-2-
pentene 260
3.5.2 (2Z,4E,6E)-EthylTrideca-2,4,6-trienoate 260
3.5.3 (2Z)-2-Allyl-3,7-dimethylocta-2,6-dien-1-ol 260
3.5.4 Ethyl2-(4-Phenylbuta-1,3-diynyl)benzoate 261
Contents IX
3.5.4.1 (E)-1-Chloro-4-phenyl-1-buten-3-yne 261
3.5.4.2 Ethyl2-(4-Phenylbuta-1,3-diynyl)benzoate 261
3.5.5 O-tert-Butyldiphenylsilyl-protected
(3S,5E)-3,9-Dimethyl-6-isopropyl-5,8-decadien-1-ol 261
3.5.5.1 (1E)-1-Iodo-2-isopropyl-5-methyl-1,4-hexadiene 261
3.5.5.2 O-tert-Butyldiphenylsilyl-protected
(3S,5E)-3,9-Dimethyl-6-isopropyl-5,8-decadien-1-ol 262
3.5.6 1,3-Diphenylpropyne 262
3.5.7 (4S)-4-Phenyl-1-pentene 263
3.5.8 (R)-2-Phenylpropan-1-ol 263
Acknowledgments 263
References 264
4 Carbon–CarbonBondFormingReactionsMediatedbyOrganozinc
Reagents 279
FabriceChemla,FranckFerreira,OlivierJackowski,LaurentMicouin,and
AlejandroPerez-Luna
4.1 Introduction 279
4.2 MethodsofPreparationofZincOrganometallics 280
4.2.1 DirectInsertionofZn(0)intoOrganohalides 280
4.2.2 TransmetallationReactions 282
4.2.2.1 TransmetallationReactionswithMain-GroupandTransitionMetal
Organometallics 282
4.2.2.2 Boron–ZincExchangeReactions 285
4.2.3 DirectZincationReactions 287
4.2.4 Halogen–ZincExchangeReactions 288
4.2.5 Hydro-andCarbozincationReactions 290
4.3 UncatalyzedCross-CouplingReactionsofOrganozincReagents 291
4.4 Copper-CatalyzedCross-CouplingReactionsofOrganozinc
Reagents 293
4.4.1 Cross-CouplingwithC(sp)-orC(sp2)-Electrophiles 293
4.4.2 Cross-CouplingReactionswithC(sp3)-Electrophiles 295
4.5 Transition-Metal-CatalyzedCross-CouplingReactionsofOrganozinc
Reagents 296
4.5.1 Cross-CouplingReactionsofC(sp2)-OrganozincReagents 297
4.5.1.1 Palladium-CatalyzedCross-CouplingReactions 297
4.5.1.2 Nickel-CatalyzedCross-CouplingReactions 311
4.5.1.3 Rhodium-CatalyzedCross-CouplingReactions 315
4.5.1.4 Cobalt-CatalyzedCross-CouplingReactions 316
4.5.1.5 Iron-CatalyzedCross-CouplingReactions 317
4.5.2 Cross-CouplingReactionsofAlkynylzincReagents 318
4.5.2.1 Cross-CouplingwithC(sp2)-Electrophiles 318
4.5.2.2 Cross-CouplingwithC(sp3)-Electrophiles 320
4.5.3 Cross-CouplingReactionsofC(sp3)-OrganozincReagents 321
4.5.3.1 Palladium-CatalyzedCross-CouplingReactions 322