Modern Organonickel Chemistry

346 Pages·3.456 MB·English

by  Tamaru Yo. (Ed.)

ModernOrganonickel
Chemistry
EditedbyYoshinaoTamaru
ModernOrganonickelChemistry. EditedbyY.Tamaru
Copyright82005WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim
ISBN:3-527-30796-6
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Modern Organonickel Chemistry
Edited by Yoshinao Tamaru
Editor 9 AllbookspublishedbyWiley-VCHare
carefullyproduced.Nevertheless,authors,
ProfessorDr.YoshinaoTamaru editors,andpublisherdonotwarrantthe
DepartmentofAppliedChemistry informationcontainedinthesebooks,
FacultyofEngineering includingthisbook,tobefreeoferrors.
NagasakiUniversity Readersareadvisedtokeepinmindthat
1-14Bunkyo-machi statements,data,illustrations,procedural
Nagasaki852-8521 detailsorotheritemsmayinadvertentlybe
Japan inaccurate.
LibraryofCongressCardNo.:Appliedfor
CoverPicture BritishLibraryCataloging-in-Publication
ThefrontcoverisshowingaKabukiactor Data:Acataloguerecordforthisbookis
dressedlikeadevil,drawnbySharaku. availablefromtheBritishLibrary.
Nickelwasfirstisolatedin1751froman
orereferredtoas‘‘devilNickcopper’’. BibliographicinformationpublishedbyDie
Minersnamedtheoreinthatwaybecause DeutscheBibliothek
itresembledcopperore,butdidnotyield DieDeutscheBibliothekliststhis
theirobjectivecopper.(OldNick,informal publicationintheDeutsche
thedevil;Satan,fromWebster’sUnabridged Nationalbibliografie;detailedbibliographic
Dictionary).Nickelwasnamedafterits dataisavailableintheInternetathttp://
accursednickname.Reproducedwith dnb.ddb.de
permissionoftheTokyoNationalMuseum.
(2005WILEY-VCHVerlagGmbH&Co.
KGaA,Weinheim
Allrightsreserved(includingthoseof
translationinotherlanguages).Nopartof
thisbookmaybereproducedinanyform–
nortransmittedortranslatedintomachine
languagewithoutwrittenpermission
fromthepublishers.Registerednames,
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whennotspecificallymarkedassuch,are
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PrintedintheFederalRepublicof
Germany.
Printedonacid-freepaper.
Typesetting AscoTypesetters,HongKong
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ISBN-13 978-3-527-30796-8
ISBN-10 3-527-30796-6
v
Contents
Preface xi
ListofContributors xv
Abbreviations xvii
1 IntroductoryGuidetoOrganonickelChemistry 1
YoshinaoTamaru
1.1 TheCrystalField 2
1.2 NickelhasWings:TheMondMethod 3
1.3 TheLigandField 3
1.4 TheFormalOxidationNumber 6
1.5 The16-and18-ElectronRule 8
1.6 TheStructure,Reactivity,andElectronicConfigurationofNickel-
Complexes 11
1.7 TheElementaryReactions 15
1.7.1 OxidativeAddition 15
1.7.2 Insertion 18
1.7.3 Transmetallation 20
1.7.4 ReductiveElimination 23
1.7.5 b-HydrogenElimination 26
1.7.6 a-andb-CarbonElimination(CaCBondCleavage) 28
1.8 CatalyticReactions 29
References 37
2 Nickel-catalyzedCross-couplingReactions 41
TamotsuTakahashiandKen-ichiroKanno
2.1 Cross-couplingofAlkylElectrophileswithOrganometallic
Compounds 41
2.2 Cross-couplingofAlkenylElectrophileswithOrganometallic
Compounds 45
2.3 Cross-couplingofAllylElectrophileswithOrganometallic
Compounds 47
ModernOrganonickelChemistry. EditedbyY.Tamaru
Copyright82005WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim
ISBN:3-527-30796-6
vi Contents
2.4 Cross-couplingofArylElectrophileswithOrganometallic
Compounds 48
2.5 AsymmetricCross-couplingReactions 53
References 53
3 ReactionofAlkenesandAllylAlcoholDerivatives 56
YuichiKobayashi
3.1 HydrovinylationofOlefins 56
3.2 HydrocyanationofOlefins 59
3.3 Heck-typeCyclization 60
3.4 OlefinInsertion 61
3.5 Nickel-catalyzedHydrozincationofOlefins 64
3.6 Ni-catalyzedAdditionofOrganometallicstoElectron-deficient
Olefins 65
3.6.1 TheReactionwithOrganometallics 65
3.6.2 TheReactionwithOrganicHalidesasNucleophiles 68
3.7 PolymerizationofEthyleneanda-OlefinsusingNi(II)-based
Catalysts 70
3.8 TheNucleophilicReactionsofp-AllylnickelComplexes 72
3.9 p-AllylnickelComplexesfromEnones 74
3.10 CarbonylativeCycloadditionofAllylicHalidesandAcetylenes 75
3.11 NucleophilicAllylationTowardp-AllylnickelComplexes 77
3.11.1 AllylationwithGrignardReagents 77
3.11.2 AllylationwithSoftNucleophiles 80
3.11.3 RegiochemicalControlBasedonInternalChelation 80
3.11.4 OrganometallicsotherthanGrignardReagentsforAllylation 82
3.11.4.1 Ni-catalyzedAllylationwithLithiumBoratesDerivedfromTrimethyl
Borate 82
3.11.4.2 AllylationwithLithiumBoratesDerivedfromAcetylene 84
3.11.4.3 AllylationwithBoratesDerivedfromCyclicBoronateEsters 85
3.11.5 TheDesignofFunctionalizedReagentsforAllylation 85
3.11.6 Nickel-catalyzedReactionsofCyclopentenylAcetateandBorates 87
3.11.7 SyntheticApplicationofNickel-catalyzedReactionsofCyclopentenyl
AcetateandBorates 89
3.11.8 ExtensionoftheLithiumBorate/NickelCatalystforCouplingwith
AlkenylandArylSubstrates 91
3.12 NickelEnolates 92
3.12.1 ReactionsofNi(II)ComplexeswithLithiumorPotassium
Enolates 93
3.12.2 TheReformatsky-typeReaction 95
3.12.3 OtherReactionsthroughNickelEnolates 96
References 97
4 ReactionofAlkynes 102
Shin-ichiIkeda
4.1 Hydrogenation 103
Contents vii
4.2 HydrometallationandRelatedReactions 104
4.2.1 HydrosilylationandHydrostannylation 104
4.2.2 Hydroboration 106
4.2.3 Hydroalumination 107
4.2.4 Miscellaneous:theAdditionofHaPandHaSGroups 107
4.3 bis-Metallation 107
4.3.1 bis-Silylationandbis-Germylation 108
4.3.2 SilaborationandGeraboration 110
4.4 Hydrocyanation,Hydroacylation,andRelatedReactions 111
4.5 CarbometallationandRelatedReactions 113
4.5.1 Carbomagnesiation 113
4.5.2 Carbozincation 114
4.5.3 Carbostannylation 115
4.5.4 Miscellaneous 117
4.6 TheSequentialReaction 118
4.6.1 SequentialReactionStartingwithActivationofOrganicHalides 118
4.6.2 SequentialReactionwithEnones 123
4.6.3 SequentialReactionwithAldehydesandImines 127
4.6.4 SequentialReactionwithEpoxides 129
4.7 Addenda 131
References 132
5 ReactionofDienesandAllenes 137
MasanariKimuraandYoshinaoTamaru
5.1 DimerizationandPolymerizationof1,3-Dienes 137
5.1.1 StructureofNi-(butadiene) ComplexesStabilizedbyPhosphine
2
Ligands 138
5.1.2 DimerizationofSubstituted1,3-Dienes 139
5.1.3 Ni-catalyzedPolymerizationofButadiene 141
5.1.4 Stereo-andRegioselectivePolymerizationofConjugatedCyclic
Dienes 143
5.2 AllylationandHomoallylationofAldehydeswithDienesand
Allenes 143
5.2.1 AllylationofAldehydesviaDimerizationof1,3-Dienes 143
5.2.2 AllylationofAldehydeswithDienesPromotedbySilane
(R4(cid:1)nSiHn) 145
5.2.3 AllylationofAldehydeswithDienesPromotedbyDiisobutylaluminum
Hydride(DIBAL)orDiisobutylaluminum(III)(acac) 147
5.2.4 HomoallylationofAldehydesPromotedbyTriethylboraneor
Diethylzinc 151
5.2.5 AllylationofAldehydesPromotedbyDimethylzinc,Trimethyborane,and
RelatedCompounds:theThree-componentConnectionReactions 154
5.2.6 TheMulti-componentConnectionReaction 157
5.2.7 CyclizationofAllenylAldehydes 158
5.3 AdditionReactionofHXonDienesandAllenes 160
5.3.1 AdditionofActiveMethyleneCompoundsto1,3-Dienes 160
viii Contents
5.3.2 Hydrocyanationof1,3-Dienes 160
5.3.3 Hydroaminationof1,3-DienesandAllenes 161
5.3.4 1,4-Dialkenylationof1,3-Dienes 162
5.3.5 AdditionofSiaBandCsp2aBCompoundson1,3-Dienes 163
5.3.6 Carbostannylationof1,3-DienesandAllenes 164
5.3.7 CarbozirconationofAllenes 166
5.3.8 Wurtz-typeCouplingReactionofOrganicHalidesandGrignard
ReagentsMediatedbytheButadiene–NickelComplex(5.1) 167
5.3.9 CarbosilylationofDieneDimers 168
References 168
6 CyclooligomerizationandCycloisomerizationofAlkenesandAlkynes 171
ShinichiSaito
6.1 CyclooligomerizationofAlkenes 171
6.2 CycloisomerizationofAlkenes 174
6.3 CyclooligomerizationofAlkynes 175
6.3.1 CyclotrimerizationofAlkynes 175
6.3.2 Co-cyclotrimerizationandCycloisomerizationofAlkynes 178
6.3.3 Co-cyclotrimerizationofAlkyneswithotherUnsaturated
Compounds 180
6.3.4 CyclotetramerizationofAlkynes 183
6.3.5 Co-cyclotetramerizationofAlkynes 185
6.4 CyclooligomerizationofDienes 185
6.4.1 CyclodimerizationandCyclotrimerizationof1,3-Butadiene 186
6.4.2 CyclodimerizationandCyclotrimerizationofSubstituted
1,3-Dienes 188
6.4.3 Co-cyclooligomerizationof1,3-Dienes 189
6.4.4 Co-cycloisomerizationof1,3-Dienes 191
6.5 CyclooligomerizationofAllenesandCumulenes 192
6.5.1 CyclooligomerizationofAllene(1,2-Propadiene) 192
6.5.2 CyclooligomerizationofSubstitutedAllenes 194
6.5.3 CyclooligomerizationofCumulenes 195
6.6 CyclooligomerizationandCycloisomerizationofMiscellaneous
Compounds 197
References 198
7 Nickel-mediatedand-catalyzedCarboxylation 205
MiwakoMoriandMasanoriTakimoto
7.1 Nickel-mediatedor-catalyzedCarboxylationof1,3-Diene 205
7.2 Nickel-mediatedor-catalyzedCarboxylationofAlkyne 211
7.3 Nickel-mediatedCarboxylationofAlkene 215
7.4 Nickel-mediatedCarboxylationofAllene 218
7.5 VariousNickel-mediatedCarboxylations 220
7.6 Perspectives 222
References 222
Contents ix
8 CarbonylationandDecarbonylation 224
YoshinaoTamaru
8.1 Decarbonylation 224
8.2 ElectrochemicalCarbonylation 227
8.2.1 MethodA:UtilizationofCO 228
8.2.2 MethodB:UtilizationofCO2 asaCOSource 228
8.2.3 MethodC:UtilizationofFe(CO)5 asaCOSource 228
8.3 TerminationofCascadeReactionsbyCarbonylation 229
8.4 CarbonylationFormingCarboxylicAcidunderPhase-Transfer
Conditions 231
References 238
9 AsymmetricSynthesis 240
RyoShintaniandTamioHayashi
9.1 TheCross-couplingReaction 240
9.2 AllylicSubstitution 246
9.2.1 AllylicSubstitutionbyCarbonNucleophiles 246
9.2.2 AllylicSubstitutionbyHydrideNucleophiles 249
9.3 HydrocyanationandHydrovinylationReactions 250
9.4 ReactionsofOrganometallicReagentswithAldehydesandEnones 255
9.4.1 ReactionwithAldehydes 255
9.4.2 ReactionwithEnones 256
9.5 ActivationofCarbonylCompoundsforCycloadditionandOtherRelated
Reactions 260
9.5.1 TheDiels–AlderReaction 260
9.5.2 The1,3-DipolarCycloadditionReaction 262
9.5.3 TheEneReactionandConjugateAdditionReaction 263
9.5.4 AdditionofNickel-EnolateIntermediates 267
9.6 OtherReactions 269
References 269
10 HeterogeneousCatalysis 273
TsutomuOsawa
10.1 HeterogeneousCatalystsandCatalyticReactions 273
10.1.1 ComparisonofHeterogeneousandHomogeneousCatalystsand
CatalyticReactions 274
10.1.2 ReactionsoverHeterogeneousCatalystsinLiquids 275
10.2 HeterogeneousNiCatalysts 276
10.2.1 ReactionsinthePetroleumIndustry 276
10.2.2 TransformationofOrganicFunctionalGroups 278
10.2.2.1 RaneyNickel 280
10.2.2.2 NickelBoride 282
10.2.2.3 SupportedNickelCatalysts 283
10.3 AsymmetricSynthesesoverHeterogeneousNickelCatalysts 285
10.3.1 Diastereo-differentiatingReactions 285