Homogeneous Catalysis for Unreactive Bond Activation

645 Pages·2014·4.808 MB·English

by  Zhang-Jie Shi

HOMOGENEOUS
CATALYSIS FOR
UNREACTIVE BOND
ACTIVATION

HOMOGENEOUS
CATALYSIS FOR
UNREACTIVE BOND
ACTIVATION
Editedby
ZHANG-JIE SHI
ProfessorofChemistry
CollegeofChemistryandMolecularEngineering
PekingUniversity
Beijing,China
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LibraryofCongressCataloging-in-PublicationData:
Homogeneouscatalysisforunreactivebondactivation/editedbyDr.Zhang-JieShi,professorof
chemistry,CollegeofChemistryandMolecularEngineering,PekingUniversity,Beijing,China.
pagescm
Includesbibliographicalreferencesandindex.
ISBN978-1-118-45223-3(hardback)
1.Homogeneouscatalysis.2.Carbon,Activated.3.Chemicalbonds.I.Shi,Zhangjie,1974-editor.
QD505.H6482014
541′.395–dc23
2014008375
PrintedintheUnitedStatesofAmerica.
10987654321
CONTENTS
PREFACE xi
CONTRIBUTORS xv
1 CATALYSISINC–ClACTIVATION 1
Zhong-XiaWangandWang-JunGuo
1.1 Introduction / 3
1.2 ReductiveDechlorination / 3
1.2.1 H asReductant / 3
2
1.2.2 ROHorROMasReductant / 6
1.2.3 HydrosilanesasReductant / 8
1.2.4 FormicAcidorItsSaltsasReductant / 11
1.2.5 BoraneorSodiumBorohydrideasReductant / 12
1.2.6 GrignardReagentsasReductant / 13
1.2.7 HydrazineasReductant / 14
1.3 FormationofC–CBonds / 14
1.3.1 SuzukiReaction / 14
1.3.2 NegishiReaction / 47
1.3.3 KumadaReaction / 57
1.3.4 StilleReaction / 70
1.3.5 HiyamaReaction / 74
1.3.6 SonogashiraReaction / 81
v
vi CONTENTS
1.3.7 DecarboxylativeCross-Coupling / 86
1.3.8 HeckReaction / 89
1.3.9 C–HFunctionalizationwithOrganicChlorides / 97
1.4 FormationofC–NBonds / 119
1.4.1 CopperCatalysts / 119
1.4.2 PalladiumCatalysts / 124
1.4.3 NickelCatalysts / 141
1.4.4 IronandCobaltCatalysts / 143
1.5 FormationofC–OBonds / 143
1.5.1 CopperCatalysts / 143
1.5.2 PalladiumCatalysts / 145
1.6 FormationofC–SBonds / 148
1.6.1 CopperCatalysts / 149
1.6.2 PalladiumCatalysts / 149
1.7 FormationofC–BBonds / 151
1.7.1 PalladiumCatalysts / 151
1.7.2 NickelCatalysts / 152
1.8 ConclusionandOutlook / 154
References / 155
2 HOMOGENEOUSTRANSITION-METAL-CATALYZED
C–FACTIVATION 203
Shang-DongYang
2.1 Background / 203
2.2 Transition-Metal-MediatedCross-CouplingReactions
byC–FBondActivation / 205
2.2.1 Nickel-MediatedC–FBondActivation / 206
2.2.2 Palladium-MediatedC–FBondActivation / 219
2.2.3 Platinum-MediatedC–FBondActivation / 225
2.2.4 Cobalt-andRhodium-MediatedC–FBondActivation / 227
2.2.5 Other-Metals-MediatedC–FBondActivation / 231
2.3 Transition-Metal-CatalyzedSubstitutionbyC–FBond
Activation / 234
2.4 Transition-Metal-PromotedDehydrofluorinationbyC–FBond
Activation / 241
2.5 TheApplicationsofC–FActivationinOrganicSynthesis / 250
2.6 SummaryandOutlook / 257
References / 259
CONTENTS vii
3 HOMOGENEOUSTRANSITION-METALCATALYZED
C–NACTIVATION 269
Xiao-BingWan
3.1 Background / 269
3.2 Palladium-CatalyzedC–NActivation / 270
3.3 Ruthenium-CatalyzedC–NActivation / 285
3.4 Nickel-CatalyzedC–NActivation / 289
3.5 Copper-CatalyzedC–NActivation / 292
3.6 Iron-CatalyzedC–NActivation / 296
3.7 Other-Transition–Metal-CatalyzedC–NActivation / 302
3.8 ComputationallyandExperimentallyMechanisticStudies / 313
3.9 SummaryandOutlook / 315
References / 315
4 CATALYTICCARBON–SULFURBONDACTIVATION
ANDTRANSFORMATIONS 317
ZhengkunYu
4.1 Background / 317
4.2 C–SBondActivationbyTransitionMetalCompounds / 318
4.3 CatalyticC–SCleavageinThioesters / 321
4.4 CatalyticC–SCleavageinDithioacetals / 325
4.5 DiverseCatalyticC–SCleavage / 331
4.6 SummaryandOutlook / 337
References / 337
5 HOMOGENEOUSTRANSITION-METAL-CATALYZEDC–O
BONDACTIVATION 347
Da-GangYu,ShuangLuo,FeiZhao,andZhang-JieShi
5.1 Introduction / 348
5.2 Palladium-CatalyzedC–OBondActivation / 354
5.2.1 Kumada–Tamao–CorriuCoupling / 354
5.2.2 NegishiCoupling(IncludingZinc,Aluminum,
andManganeseReagents) / 356
5.2.3 StilleCoupling / 357
5.2.4 Suzuki–MiyauraCoupling / 359
5.2.5 HiyamaCoupling / 363
5.2.6 HeckReaction / 365
5.2.7 SonogashiraReaction / 367
viii CONTENTS
5.2.8 Cross-CouplingwithOtherC–HBondsandCarboxylic
Acids / 369
5.2.9 CarbonylationReaction / 373
5.2.10Buchwald–HartwigAmination / 374
5.2.11OtherC–XBondFormationReactions / 379
5.3 Nickel–CatalyzedC–OBondActivation / 382
5.3.1 Kumada–Tamao–CorriuReaction / 382
5.3.2 NegishiCoupling(IncludingZinc,Aluminum,Manganese,
Copper,andIndiumReagents) / 391
5.3.3 Suzuki–MiyauraCoupling / 392
5.3.4 HeckReaction / 403
5.3.5 Buchwald–HartwigAmination / 403
5.3.6 Borylation / 405
5.3.7 DirectArylation / 406
5.3.8 Reduction / 407
5.3.9 OtherReactions / 409
5.4 Other-Transition-Metal-CatalyzedC–OBondActivation / 409
5.4.1 Fe-CatalyzedC–OBondActivation / 409
5.4.2 Co-CatalyzedC–OBondActivation / 414
5.4.3 Cu-CatalyzedC–OBondActivation / 417
5.4.4 Rh-CatalyzedC–OBondActivation / 419
5.4.5 Ru-CatalyzedC–OBondActivation / 422
5.5 SummaryandOutlook / 426
References / 427
6 HOMOGENEOUSTRANSITION-METAL-CATALYZED
C–HBONDFUNCTIONALIZATION 441
Bi-JieLiandZhang-JieShi
6.1 Overview / 442
6.2 MechanismofC–HCleavage / 444
6.2.1 OxidativeAddition / 444
6.2.2 ElectrophilicSubstitution / 448
6.2.3 SigmaBondMetathesis / 449
6.2.4 1,2-Addition / 450
6.2.5 MetalloradicalActivation / 452
6.3 DirectedC–HOxidation / 453
6.3.1 DirectedC–HOxygenation / 454
6.3.2 DirectedC–HAmination / 455