Editedby LutzF.Tietze DominoReactions RelatedTitles Hanessian,S.,Giroux,S.,Merner,B.L. Carreira,E.M.,Kvaerno,L. DesignandStrategyinOrganic ClassicsinStereoselective Synthesis Synthesis FromtheChironApproachtoCatalysis 2009 2013 PrintISBN:978-3-527-32452-1 PrintISBN:978-3-527-33391-2 Xu,P.,Wang,W.(eds.) Pignataro,B.(ed.) CatalyticCascadeReactions NewStrategiesinChemical SynthesisandCatalysis 2013 PrintISBN:978-1-118-01602-2, 2012 alsoavailableindigitalformats PrintISBN:978-3-527-33090-4, alsoavailableindigitalformats Zhang,W.,Cue,B.W.(eds.) GreenTechniquesforOrganic Majumdar,K.C.,Chattopadhyay,S.K. (eds.) SynthesisandMedicinal Chemistry HeterocyclesinNaturalProduct Synthesis 2012 PrintISBN:978-0-470-71151-4, 2011 alsoavailableindigitalformats PrintISBN:978-3-527-32706-5, alsoavailableindigitalformats Starkey,L. Majumdar,K.C.,Chattopadhyay,S.K. IntroductiontoStrategiesfor (eds.) OrganicSynthesis HeterocyclesinNaturalProduct 2012 Synthesis PrintISBN:978-1-118-18083-9 2011 PrintISBN:978-3-527-32706-5, Oestreich,M.M.(ed.) alsoavailableindigitalformats TheMizoroki-HeckReaction- TheHeckReaction Nicolaou,K.C.,Chen,J.S. ClassicsinTotalSynthesisIII 2009 FurtherTargets,Strategies,Methods PrintISBN:978-0-470-03394-4, alsoavailableindigitalformats 2011 PrintISBN:978-3-527-32958-8 EditedbyLutzF.Tietze Domino Reactions ConceptsforEfficientOrganicSynthesis Editor AllbookspublishedbyWiley-VCHare carefullyproduced.Nevertheless,authors, Prof.Dr.LutzF.Tietze editors,andpublisherdonotwarrantthe Georg-AugustUniversity informationcontainedinthesebooks, InstituteofOrganicandBiomolecular includingthisbook,tobefreeoferrors. Chemistry Readersareadvisedtokeepinmindthat Tammannstr.2 statements,data,illustrations,procedural 37077Go¨ttingen detailsorotheritemsmayinadvertentlybe Germany inaccurate. LibraryofCongressCardNo.:appliedfor Cover JunglePhoto.Source:Fotolia©Chakka BritishLibraryCataloguing-in-Publication Data Acataloguerecordforthisbookisavailable fromtheBritishLibrary. Bibliographicinformationpublishedbythe DeutscheNationalbibliothek TheDeutscheNationalbibliothek liststhispublicationintheDeutsche Nationalbibliografie;detailedbibliographic dataareavailableontheInternetat <http://dnb.d-nb.de>. ©2014Wiley-VCHVerlagGmbH&Co. KGaA,Boschstr.12,69469Weinheim, Germany Allrightsreserved(includingthoseof translationintootherlanguages).Nopart ofthisbookmaybereproducedinany form–byphotoprinting,microfilm,orany othermeans–nortransmittedortranslated intoamachinelanguagewithoutwritten permissionfromthepublishers.Registered names,trademarks,etc.usedinthisbook, evenwhennotspecificallymarkedassuch, arenottobeconsideredunprotectedbylaw. PrintISBN:978-3-527-33432-2 ePDFISBN:978-3-527-67133-5 ePubISBN:978-3-527-67132-8 MobiISBN:978-3-527-67131-1 oBookISBN:978-3-527-67130-4 CoverDesign Adam-Design,Weinheim, Germany Typesetting LaserwordsPrivateLtd., Chennai,India PrintingandBinding MarkonoPrintMedia PteLtd,Singapore Printedonacid-freepaper PrintedinSingapore V Contents Preface XIII ListofContributors XV ListofAbbreviations XIX Introduction 1 References 4 1 Transition-Metal-CatalyzedCarbonylativeDominoReactions 7 Xiao-FengWu,HelfriedNeumann,andMatthiasBeller 1.1 Introduction 7 1.2 Transition-Metal-CatalyzedCarbonylativeDominoReactions 8 1.2.1 Ruthenium-CatalyzedCarbonylativeDominoReactions 8 1.2.2 Rhodium-CatalyzedCarbonylativeDominoReactions 13 1.2.3 Palladium-CatalyzedCarbonylativeDominoReactions 16 1.2.4 Iron-,Copper-,Nickel-,andCobalt-CatalyzedCarbonylativeDomino Reactions 24 1.3 Outlook 27 References 27 2 MetathesisReactionsinDominoProcesses 31 KamalM.DawoodandPeterMetz 2.1 DominoProcessesFeaturingSolelyMetathesisEvents 31 2.1.1 ReactionsInvolvingOnlyAlkenes 31 2.1.2 ReactionsInvolvingAlkenesandAlkynes 41 2.2 DominoProcessesFeaturingMetathesisandNon-metathesis Events 52 2.2.1 Metathesis/RedoxTransformation 52 2.2.2 Metathesis/Isomerization 53 2.2.3 Metathesis/Cycloaddition 56 2.2.4 Metathesis/Substitution 58 2.2.5 Metathesis/ConjugateAddition 59 2.2.6 Metathesis/CarbonylOlefination 62 VI Contents 2.3 ConclusionandOutlook 63 Acknowledgments 63 References 63 3 C–HActivationReactionsinDominoProcesses 67 GavinChitTsuiandMarkLautens 3.1 HeckReactions/C–HActivations 67 3.2 CarbopalladationsandAminopalladationsofAlkynes/C–H Activations 72 3.3 Palladium-Catalyzed/Norbornene-MediatedorthoC–HActivations 80 3.4 DominoReactionsInvolvingHeteroatom-DirectedC–H Activations 96 3.5 Conclusions 101 References 101 4 DominoReactionsInitiatedbyNucleophilicSubstitution 105 HiriyakkanavarIla,AnandAcharya,andSaravananPeruncheralathan 4.1 DominoSN/MichaelAdditionandRelatedReactions 106 4.2 DominoReactionsInitiatedbyNucleophilicRingOpeningof Aziridines,Epoxides,andActivatedCyclopropanes 115 4.3 DominoSN/BrookRearrangements 127 References 138 5 RadicalReactionsinDominoProcesses 141 GuanghuiAnandGuigenLi 5.1 Introduction 141 5.2 Radical/CationDominoProcesses 143 5.3 Radical/AnionicDominoProcesses 148 5.4 DominoRadical/RadicalProcess 154 5.5 Radical/PericyclicDominoProcesses 172 5.6 AsymmetricRadicalDominoProcesses 174 5.6.1 ChiralAuxiliary-DirectedAsymmetricRadicalDominoProcesses 174 5.6.2 ChiralCatalyst-DrivenAsymmetricRadicalDominoProcesses 176 5.7 ConclusionandOutlook 178 Acknowledgments 179 References 179 6 PericyclicReactionsinDominoProcesses 183 LukasJ.PatalagandDanielB.Werz 6.1 Introduction 183 6.2 Cycloadditions 184 6.2.1 Cycloaddition/Cycloaddition 184 6.2.2 Cycloaddition/Cycloreversion 185 6.2.3 Cycloaddition/SigmatropicRearrangement 188 6.2.4 Cycloaddition/Electrocyclization 189 Contents VII 6.2.5 Cycloaddition/MixedTransformations 191 6.3 SigmatropicRearrangements 192 6.3.1 SigmatropicRearrangement/SigmatropicRearrangement 192 6.3.2 SigmatropicRearrangement/Cycloaddition 195 6.3.3 SigmatropicRearrangement/Electrocyclization 196 6.3.4 SigmatropicRearrangement/MixedTransformations 199 6.4 Electrocyclizations 201 6.4.1 Electrocyclization/Electrocyclization 201 6.4.2 Electrocyclization/Cycloaddition 202 6.4.3 Electrocyclization/SigmatropicRearrangement 205 6.4.4 Electrocyclization/MixedTransformations 208 6.5 MixedTransformations 209 6.5.1 MixedTransformationsFollowedbyPericyclicReactions 209 6.5.2 CascadesofCarbopalladationsFollowedbyPericyclicReactions 211 6.5.3 DominoKnoevenagel/HeteroDiels–AlderReaction 214 6.6 ConcludingRemarks 214 Acknowledgments 215 References 215 7 ModernDominoReactionsContainingaMichaelAdditionReaction 219 ScottG.Stewart 7.1 Introduction 219 7.2 FormationofAcyclicProducts 221 7.3 FormationofCarbocycles 225 7.4 Formationof O-Heterocycles 236 7.5 Formationof N-Heterocycles 250 7.6 Formationof S-Heterocycles 257 7.7 FormationofHeterocyclesContainingNitrogenandOxygen 260 References 262 8 AldolReactionsinDominoProcesses 267 ChristophSchneiderandMichaelBoomhoff 8.1 Introduction 267 8.2 DominoProcesseswiththeAldolReactionasFirstStep 267 8.2.1 Aldol-LactonizationReactions 267 8.2.2 Aldol/PrinsReactions 270 8.2.3 Aldol/AcetalizationReactions 272 8.2.4 Aldol–TishchenkoReactions 273 8.2.5 VinylogousAldol/MichaelReactions 276 8.3 DominoProcesseswiththeAldolReactionasSubsequentStep 277 8.3.1 ConjugateAddition/AldolReactions 277 8.3.1.1 AdditionofCarbonNucleophiles 277 8.3.1.2 AdditionofSulfurNucleophiles 281 8.3.1.3 AdditionofOxygenandNitrogenNucleophiles 283 8.3.1.4 Iodo-AldolReactions 285 VIII Contents 8.3.1.5 ReductiveAldolReactions 287 8.3.2 Isomerization/AldolReactions 289 8.3.3 WittigRearrangement/AldolReactions 290 8.3.4 Cycloaddition/AldolReactions 290 8.4 ConclusionandOutlook 292 References 292 9 OxidationsandReductionsinDominoProcesses 295 GovindasamySekar,IyyanarKarthikeyan,andDhandapaniGanapathy 9.1 Introduction 295 9.2 DominoReactionsInitiatedbyOxidationorReductionReaction 296 9.2.1 DominoReactionsInitiatedbyanOxidationReaction 296 9.2.2 DominoReactionsInitiatedbyReductionReaction 301 9.3 DominoReactionsHavingOxidationinMiddleoftheSequence 312 9.4 DominoReactionsTerminatedbyOxidationorReduction Reaction 313 9.4.1 DominoReactionsTerminatedbyOxidationReaction 313 9.4.2 DominoReactionsTerminatedbyReductionReaction 314 9.5 Conclusion 319 Acknowledgments 319 References 319 10 OrganocatalysisinDominoProcesses 325 He´le`nePellissier 10.1 Introduction 325 10.2 One-andTwo-ComponentDominoReactions 326 10.2.1 DominoReactionsInitiatedbytheMichaelReaction 327 10.2.1.1 DominoMichael/MichaelReactions 327 10.2.1.2 DominoMichael/AldolReactions 334 10.2.1.3 DominoMichael/IntramolecularHeterocyclizationReactions 340 10.2.1.4 DominoMichael/IntramolecularAlkylationReactions 349 10.2.1.5 DominoMichael/(aza)–HenryReactions 352 10.2.1.6 DominoMichael/KnoevenagelReactions 355 10.2.1.7 DominoMichael/aza-Morita–Baylis–HillmanReactions 357 10.2.1.8 DominoMichael/MannichReactions 357 10.2.1.9 OtherDominoReactionsInitiatedbytheMichaelReaction 359 10.2.2 DominoReactionsInitiatedbyOtherReactions 361 10.2.2.1 DominoReactionsInitiatedbytheIndirectMannichReaction 361 10.2.2.2 DominoReactionsInitiatedbythe(Aza)-Morita–Baylis–Hillman Reaction 363 10.2.2.3 DominoReactionsInitiatedbytheFriedel–CraftsReaction 364 10.2.2.4 MiscellaneousDominoReactions 365 10.3 MulticomponentReactions 371 10.3.1 MulticomponentReactionsInitiatedbytheMichaelReaction 371 10.3.1.1 MichaelReactionsofα,β-UnsaturatedAldehydes 371 Contents IX 10.3.1.2 MichaelReactionsofOtherα,β-UnsaturatedCarbonyl Compounds 378 10.3.1.3 MichaelReactionsofNitroolefins 380 10.3.2 MulticomponentReactionsInitiatedbytheKnoevenagelReaction 385 10.3.3 MulticomponentReactionsBasedontheMannichReaction 388 10.3.4 MulticomponentReactionsBasedontheBiginelliReaction 392 10.3.5 MulticomponentReactionsBasedontheHantzschReaction 394 10.3.6 MulticomponentReactionsBasedontheStreckerReaction 395 10.3.7 MulticomponentReactionsBasedonthePetasisReaction 397 10.3.8 1,3-DipolarCycloaddition-BasedMulticomponentReactions 398 10.3.9 MiscellaneousMulticomponentReactions 400 10.4 Conclusions 405 References 405 11 Metal-CatalyzedEnantio-andDiastereoselectiveC–CBond-Forming ReactionsinDominoProcesses 419 ShinobuTakizawaandHiroakiSasai 11.1 DominoReactionInitiatedbyC–CBondFormation 419 11.1.1 DominoReactionInitiatedbyConjugateAddition 419 11.1.2 DominoReactionInitiatedbyCycloaddition 433 11.1.3 DominoReactionInitiatedbyCarbometalation 435 11.2 DominoReactionInitiatedbyC–HBondFormation 435 11.2.1 DominoReactionInitiatedbyConjugateAddition 435 11.3 DominoReactionInitiatedbyC–NBondFormation 442 11.3.1 DominoReactionInitiatedbyImineFormation 442 11.3.2 DominoReactionBasedonCycloaddition 443 11.4 DominoReactionInitiatedbyC–OBondFormation 445 11.4.1 DominoReactionInitiatedbyCarbonylYlideFormation 445 11.4.2 DominoReactionInitiatedbyOxoniumYlideFormation 450 11.4.3 DominoReactionBasedonCycloaddition 452 11.4.4 DominoReactionBasedonPd(II)/Pd(IV)Catalysis 454 11.4.5 DominoReactionBasedonaWackerOxidation 454 11.5 DominoReactionInitiatedbyC–BandC–SiBondFormation 455 11.5.1 DominoReactionInitiatedbyConjugateAddition 456 11.6 ConclusionandOutlook 457 References 458 12 DominoProcessesunderMicrowaveIrradiation,HighPressure,andin Water 463 BoJiang,Shu-JiangTu,andGuigenLi 12.1 Introduction 463 12.2 Microwave-AssistedDominoReactions 464 12.2.1 IntramolecularDominoReactionsunderMicrowaveHeating 464 12.2.2 Two-ComponentDominoReactionunderMicrowaveHeating 465 12.2.3 MulticomponentDominoReactionsunderMicrowaveHeating 472
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