Transition-Metal-Mediated Aromatic Ring Construction

809 Pages·2013·7.74 MB·English

by  Ken Tanaka

TRANSITION-METAL-MEDIATED
AROMATIC RING CONSTRUCTION
TRANSITION-METAL-MEDIATED
AROMATIC RING CONSTRUCTION
Editedby
KENTANAKA
TokyoUniversityofAgricultureandTechnology
Tokyo,Japan
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LibraryofCongressCataloging-in-PublicationData:
Transition-metal-mediatedaromaticringconstruction/editedbyKenTanaka,TokyoUniversityof
AgricultureandTechnology,Tokyo,Japan.
pagescm
Includesbibliographicalreferencesandindex.
ISBN978-1-118-14892-1(hardback)
1.Aromaticcompounds—Synthesis. 2.Transitionmetalcatalysts.I.Tanaka,Ken,1967–
QD331.T732013
547(cid:3).6—dc23
2012049882
PrintedintheUnitedStatesofAmerica
10 9 8 7 6 5 4 3 2 1
CONTENTS
CONTRIBUTORS xvii
PREFACE xxi
PARTI [2+2+2]ANDRELATEDCYCLOADDITION
REACTIONS
1 Cobalt-Mediated[2+2+2]Cycloaddition 3
VincentGandon
1.1 Introduction, 3
1.2 SynthesisofBenzenes, 4
1.2.1 NewCatalyticSystems, 4
1.2.2 NewCyclizationPartners, 11
1.2.3 Chemo-andRegioselectivityIssues, 14
1.3 SynthesisofHeterocycles, 15
1.3.1 NewCatalyticSystems, 15
1.3.2 NewCyclizationPartners, 20
1.3.3 Chemo-andRegioselectivityIssues, 21
1.4 MechanisticAspects, 24
1.5 SyntheticApplications, 26
1.5.1 NaturalProductsandNaturallyOccurringScaffolds, 26
1.5.2 Polyphenylenes, 28
1.6 SummaryandOutlook, 30
References, 31
v
vi CONTENTS
2 Nickel-Mediated[2+2+2]Cycloaddition 37
PuneetKumarandJanisLouie
2.1 Introduction, 37
2.2 SynthesisofBenzenes, 37
2.3 CycloadditionofAlkynesandNitriles, 45
2.4 CycloadditionofAlkynesandImines, 49
2.5 CycloadditionofAlkynesandCarbonDioxide, 50
2.6 CycloadditionofAlkynesandIsocyanates, 51
2.7 CycloadditionofAlkynesandCarbodiimide, 54
2.8 CycloadditionofDiynesandKetenes, 54
2.9 CycloadditionofArynes, 55
2.10 Mechanism, 58
2.10.1 CouplingofAlkynesandAllene, 58
2.10.2 CycloadditionofAlkyneandNitrile, 59
2.10.3 CycloadditionofAlkynesandHeterocumulenes, 63
2.10.4 CycloadditionofArynes, 68
2.11 SummaryandOutlook, 69
References, 69
3 Ruthenium-Mediated[2+2+2]Cycloaddition 71
YoshihikoYamamoto
3.1 Introduction, 71
3.2 SynthesisofBenzenes, 72
3.2.1 Cyclotrimerization, 72
3.2.2 Cross-Cyclotrimerization, 77
3.2.3 PartiallyIntramolecularCyclotrimerizations, 80
3.2.4 FullyIntramolecularCyclotrimerization, 87
3.2.5 CyclotrimerizationofAlkynylboronatesand1-Haloalkynes, 89
3.3 SynthesisofHeterocycles, 92
3.3.1 CyclocotrimerizationofAlkyneswithNitrilestoForm
Pyridines, 92
3.3.2 CyclocotrimerizationofAlkyneswithHeterocumulenes, 98
3.4 MechanismofRuthenium-Catalyzed[2+2+2]Cycloadditions, 101
3.5 SyntheticApplications, 111
3.5.1 SynthesisofBiologicallyInterestingMolecules, 112
3.5.2 SynthesisofPolyaromaticFunctionalMolecules, 115
3.6 SummaryandOutlook, 119
References, 120
4 Rhodium-Mediated[2+2+2]Cycloaddition 127
KenTanaka
4.1 Introduction, 127
4.2 SynthesisofBenzenes, 128
CONTENTS vii
4.2.1 IntermolecularReactionsCatalyzedbyNeutralRhodium
Complexes, 128
4.2.2 IntermolecularReactionsCatalyzedbyCationicRhodium
Complexes, 131
4.2.3 IntramolecularReactionsCatalyzedbyNeutralRhodium
Complexes, 134
4.2.4 IntramolecularReactionsCatalyzedbyCationicRhodium
Complexes, 143
4.3 SynthesisofPyridines, 147
4.3.1 IntermolecularReactions, 147
4.3.2 IntramolecularReactions, 149
4.4 SynthesisofPyridonesandRelatedHeterocycles, 153
4.4.1 IntermolecularReactions, 153
4.4.2 IntramolecularReactions, 155
4.5 SummaryandOutlook, 157
References, 158
5 Iridium-Mediated[2+2+2]Cycloaddition 161
RyoTakeuchi
5.1 Introduction, 161
5.2 SynthesisofBenzeneDerivatives, 162
5.3 SynthesisofHeterocyclicCompounds, 169
5.4 MechanisticAspects, 175
5.5 SummaryandOutlook, 179
References, 179
6 [2+2+2]andRelatedCycloadditionsMediatedbyOther
TransitionMetals 183
KenTanakaandYuShibata
6.1 Introduction, 183
6.2 Palladium-Catalyzed[2+2+2]and[2+2+1]
Cycloadditions, 183
6.2.1 [2+2+2]Cycloaddition, 183
6.2.2 [2+2+1]Cycloaddition, 193
6.3 Iron-Catalyzed[2+2+2]Cycloaddition, 196
6.4 Manganese-Catalyzed[2+2+2]Cycloaddition, 199
6.5 Rhenium-Catalyzed[2+2+2],[2+1+2+1],and
[2+2+1+1]Cycloadditions, 200
6.6 OtherTransition-Metal-Catalyzed[2+2+2]
Cycloaddition, 202
6.7 SummaryandOutlook, 203
References, 203
viii CONTENTS
7 ApplicationtotheSynthesisofNaturalProducts 207
BernhardWitulskiandJulienGrand
7.1 Introduction, 207
7.2 ConstructionofBenzeneRings, 209
7.2.1 ApplicationtotheSynthesisofSteroids, 209
7.2.2 ApplicationsoftheIntramolecular[2+2+2]
CycloadditionReaction, 212
7.2.3 ApplicationoftheCrossedVersionofthe[2+2+2]
AlkyneCycloadditionReaction, 219
7.3 ConstructionofaHeterocyclicRing, 226
7.4 Miscellaneous, 231
7.5 SummaryandOutlook, 238
References, 239
8 SynthesisofPlanarChiralAromaticCompoundsvia[2+2+2]
Cycloaddition 243
TakanoriShibataandKenTanaka
8.1 Introduction, 243
8.2 Cobalt-Catalyzed[2+2+2]Cycloaddition, 246
8.3 Rhodium-Catalyzed[2+2+2]Cycloaddition, 247
8.4 Enantioselective[2+2+2]Cycloaddition, 249
8.5 SummaryandOutlook, 252
References, 252
9 SynthesisofAxiallyChiralAromaticCompoundsvia[2+2+2]
Cycloaddition 255
KenTanakaandTakanoriShibata
9.1 Introduction, 255
9.2 Cobalt-CatalyzedEnantioselective[2+2+2]Cycloaddition, 256
9.3 Iridium-CatalyzedEnantioselective[2+2+2]Cycloaddition, 258
9.4 Rhodium-CatalyzedEnantioselective[2+2+2]Cycloaddition, 263
9.4.1 SynthesisofBiarylsandTeraryls, 263
9.4.2 SynthesisofBiarylsandTetraphenylenesviaDouble
Cycloaddition, 266
9.4.3 SynthesisofHeterobiaryls, 269
9.4.4 SynthesisofBiarylPhosphorusCompounds, 270
9.5 EnantioselectiveSynthesisofAxiallyChiralAnilidesand
Bezamides, 275
9.5.1 SynthesisofAnilides, 275
9.5.2 SynthesisofBenzamides, 277
9.6 SummaryandOutlook, 278
References, 278
CONTENTS ix
10 SynthesisofHelicallyChiralAromaticCompoundsvia[2+2+2]
Cycloaddition 281
KenTanaka
10.1 Introduction, 281
10.2 NonasymmetricSynthesis, 281
10.3 DiastereoselectiveSynthesis, 287
10.4 EnantioselectiveSynthesis, 290
10.5 SummaryandOutlook, 296
References, 297
11 AromaticRingConstructionfromZirconocenesandTitanocenes 299
ShiLiandTamotsuTakahashi
11.1 Introduction, 299
11.2 AromaticRingConstructionfromZirconocenes, 300
11.2.1 [2+2+2]and[2+2+1]Cycloadditions, 300
11.2.2 CouplingReactions, 311
11.3 AromaticRingConstructionfromTitanocenes, 313
11.4 ApplicationtoSynthesisofSubstitutedAcenes, 315
11.5 SummaryandOutlook, 317
References, 318
PARTII [4+2],[3+2],ANDRELATEDCYCLOADDITION
REACTIONS
12 [4+2]and[3+2]CycloadditionviaMetallacycles 323
TakuyaKurahashiandSeijiroMatsubara
12.1 Introduction, 323
12.2 [4+2]CycloadditionviaEliminationofSmallMolecules, 326
12.3 [3+2]CycloadditionviaEliminationofSmallMolecules, 332
12.4 [4+2]CycloadditionviaC CBondActivation, 334
12.5 [4+2]CycloadditionviaC–HBondActivation, 336
12.6 SummaryandOutlook, 339
References, 339
13 Diels–AlderReactions 341
GerhardHiltandFlorianPu¨nner
13.1 Introduction, 341
13.2 Transition-Metal-MediatedDiels–AlderReaction/Aromatization
Sequence, 342
13.3 IntramolecularDiels–AlderReactionstowardDihydroaromatic
andAromaticProducts, 349
x CONTENTS
13.4 SyntheticApplications, 350
13.5 SummaryandOutlook, 352
References, 352
14 [4+2]BenzannulationofEnyneswithAlkynes 355
VladimirGevorgyanandOlgaV.Zatolochnaya
14.1 Introduction, 355
14.2 BenzannulationofEnynewithAlkyne:Gold-catalyzed
BenzannulationReaction, 356
14.3 BenzannulationofEnynewithEnyne, 358
14.3.1 Palladium-Catalyzed[4+2]Homo-benzannulation
Reaction, 358
14.3.2 Cobalt-Catalyzed[4+2]Homo-benzannulationReaction, 363
14.4 BenzannulationofEnynewithDiyne, 365
14.5 SyntheticApplications, 371
14.6 SummaryandOutlook, 376
References, 376
15 Formal[4+2]BenzannulationviaPyryliumIntermediates 379
NaokiAsaoandYoshifumiIshikawa
15.1 Introduction, 379
15.2 BenzannulationofPyryliumSalts, 380
15.3 BenzannulationofO-Alkynylbenzaldehydes, 380
15.3.1 WithAlkynes, 380
15.3.2 WithAlkenesorEnolEthers, 387
15.3.3 WithCarbonylCompounds, 390
15.3.4 WithOtherDienophiles, 391
15.4 Intramolecular[4+2]Benzannulation, 392
15.5 ApplicationtoNaturalProductSynthesis, 394
15.6 SummaryandOutlook, 395
References, 396
16 Utilizationof1,3-DipolarCompounds 399
Yi-FengWangandShunsukeChiba
16.1 Introduction, 399
16.2 1,3-DipolarCycloaddition, 401
16.2.1 Azides, 401
16.2.2 Diazoalkanes, 403
16.2.3 CarbonylYlides, 406
16.2.4 AzomethineYlides, 407
16.3 Five-MemberedRingConstructionviaDecompositionofAzides, 410
16.3.1 UseofVinylAzides, 410
16.3.2 UseofArylAzides, 413
16.3.3 UseofAlkylAzides, 417
CONTENTS xi
16.4 Six-MemberedRingConstructionviaDecompositionofAzides, 418
16.4.1 UseofVinylAzides, 418
16.4.2 UseofCyclic2-AzidoAlcohols, 420
16.4.3 Useof(cid:2)-AzidoCarbonylCompounds, 420
16.5 SummaryandOutlook, 421
References, 422
17 UtilizationofTransition-MetalCarbenoids 425
JamesWallaceHerndon,Jr.
17.1 Introduction, 425
17.2 Five-memberedAromaticRingConstruction, 426
17.2.1 PyrroleConstruction, 426
17.2.2 InterchangeablePyrroleandFuranConstruction, 428
17.2.3 FuranRingConstruction, 431
17.3 Six-MemberedAromaticRingConstruction, 432
17.3.1 Do¨tzBenzannulationReaction, 432
17.3.2 Mechanism-BasedAlternativeBenzannulation, 441
17.3.3 BenzannulationUnrelatedtotheDo¨tzReaction, 447
17.3.4 PyridineSyntheses, 448
17.3.5 SynthesisofPyronesandPyranylideneComplexes, 448
17.4 SummaryandOutlook, 450
References, 450
PARTIII ELECTROCYCLIZATIONREACTIONS
18 IntramolecularHydroarylationofAlkynes,Alkenes,andAllenes 457
TsugioKitamura
18.1 Introduction, 457
18.2 IntramolecularHydroarylation, 457
18.2.1 SynthesisofCarbocycles, 457
18.2.2 SynthesisofOxygenHeterocycles, 467
18.2.3 SynthesisofNitrogenHeterocycles, 470
18.2.4 SyntheticApplications, 477
18.3 SummaryandOutlook, 482
References, 483
19 IntramolecularC XBondFormationbetweenC XorX Hand
Alkynes 485
HiroakiOhno
19.1 Introduction, 485
19.2 C XBondFormationbetweenC XandAlkynes, 485
19.2.1 PyridineFormation, 485