Catalyzed Carbon-Heteroatom Bond Formation

523 Pages·2010·6.57 MB·English

by  Andrei K. Yudin

Y Edited by Andrei K. Yudin
u
W d
ritten by an experienced editor widely acclaimed within the scientifi c i
n
community, this book covers everything from oxygen to nitrogen func-

tionalities. (
E Catalyzed
d
From the contents: .
)
(cid:2) Palladium-Catalyzed Syntheses of Five-Membered Saturated
Heterocycles and of Aromatic Heterocyles
Carbon-Heteroatom
(cid:2) Palladium-Catalysis for Oxidative 1,2-Difunctionalization of Alkenes
(cid:2) Rhodium-Catalyzed Amination of C-H-Bonds
(cid:2) Carbon-Heteroatom Bond Formation by Rh(I)-Catalyzed
Ring-Opening Reactions
(cid:2) Transition Metal-Catalyzed Synthesis of Lactones and of Monocyclic Bond Formation
and Fused Five-Membered Aromatic Heterocycles
(cid:2) The Formation of Carbon-Sulfur and Carbon-Selenium Bonds
by Substitution and Addition Reactions Catalyzed by Transition
Metal Complexes
(cid:2) New Reactions of Copper Acetylides
With a Foreword by John F. Hartwig
(cid:2) Gold Catalyzed Addition of Nitrogen, Sulfur and Oxygen
Nucleophiles to C-C Multiple Bonds
The result is an indispensable source of information for the strategic
planning of the synthetic routes for organic, catalytic and medicinal
BC
chemists, as well as chemists in industry. oa
nt
a
d
l
y
Fz
oe
Andrei K. Yudin obtained his PhD degree at the University
rd
of Southern California under the direction of Professors G. m

K. Surya Prakash and George A. Olah. He then took up a C
a
post-doctoral position in the laboratory of Professor K. Barry a
t
Sharpless at the Scripps Research Institute. In 1998 he started ir
ob
his independent career at the University of Toronto where he
no
is now a Full Professor. His research interests are in the devel-
n
opment of novel synthetic methods, metal catalysis, peptide
-
chemistry, and synthesis of complex molecules of biological H
signifi cance.
e
t
e
r
o
a
t
o
m
www.wiley-vch.de

Edited by
Andrei K. Yudin
Catalyzed Carbon-Heteroatom
Bond Formation
Further Reading
Nugent,T.C. (Ed.) Drauz, K.,Gröger,H., May,O. (Eds.)
Chiral Amine Synthesis Enzyme Catalysis in Organic
Methods,Developmentsand Synthesis
Applications
2011
2010 ISBN:978-3-527-32547-4
ISBN:978-3-527-32509-2
Royer,J.,Husson, H. P.(Eds.)
Ricci, A.(Ed.)
Asymmetric Synthesis of
Amino Group Chemistry
Nitrogen Heterocycles
FromSynthesistotheLifeSciences
2009
2008 ISBN:978-3-527-32036-3
ISBN:978-3-527-31741-7
Dupont,J, Pfeffer,M. (Eds.)
Bäckvall,J.-E. (Ed.)
Palladacycles
Modern Oxidation Methods
Synthesis,Characterizationand
Applications
2011
ISBN:978-3-527-32320-3 2008
ISBN:978-3-527-31781-3
Bandini, M.,Umani-Ronchi, A. (Eds.)
Plietker, B.(Ed.)
Catalytic Asymmetric
Friedel-Crafts Alkylations Iron Catalysis in Organic
Chemistry
2009
ReactionsandApplications
ISBN:978-3-527-32380-7
2008
Bullock, R.M. (Ed.)
ISBN:978-3-527-31927-5
Catalysis without Precious
Metals
2010
ISBN:978-3-527-32354-8
Edited by
Andrei K. Yudin
Catalyzed Carbon-Heteroatom
Bond Formation
TheEditor AllbookspublishedbyWiley-VCHarecarefully
produced.Nevertheless,authors,editors,and
Prof.AndreiK.Yudin publisherdonotwarranttheinformationcontained
UniversityofToronto inthesebooks,includingthisbook,tobefreeof
DepartmentofChemistry errors.Readersareadvisedtokeepinmindthat
St.GeorgeStreet80 statements,data,illustrations,proceduraldetailsor
Toronto,ONM5S3H6 otheritemsmayinadvertentlybeinaccurate.
Canada
LibraryofCongressCardNo.: appliedfor
BritishLibraryCataloguing-in-PublicationData
Acataloguerecordforthisbookisavailablefromthe
BritishLibrary.
Bibliographicinformationpublishedby
theDeutscheNationalbibliothek
TheDeutscheNationalbibliothekliststhis
publicationintheDeutscheNationalbibliografie;
detailedbibliographicdataareavailableonthe
Internetathttp://dnb.d-nb.de.
#2011WILEY-VCHVerlag&Co.KGaA,
Boschstr.12,69469Weinheim,Germany
Allrightsreserved(includingthoseoftranslationinto
otherlanguages).Nopartofthisbookmaybe
reproducedinanyform–byphotoprinting,
microfilm,oranyothermeans–nortransmittedor
translatedintoamachinelanguagewithoutwritten
permissionfromthepublishers.Registerednames,
trademarks,etc.usedinthisbook,evenwhennot
specificallymarkedassuch,arenottobeconsidered
unprotectedbylaw.
Composition ThomsonDigital,Noida
PrintingandBinding FabulousPrintersPte.Ltd.,
Singapore
CoverDesign SchulzGrafik-Design,Fußgönheim
PrintedinSingapore
Printedonacid-freepaper
ISBN:978-3-527-32428-6
V
Contents
Preface XIII
List of Contributors XV
1 SynthesisofSaturatedFive-MemberedNitrogenHeterocycles
viaPd-CatalyzedC–NBond-FormingReactions 1
JohnP.Wolfe,JoshuaD.Neukom,andDuyH.Mai
1.1 Introduction 1
1.2 Pd-CatalyzedAminationofArylHalides 1
1.3 SynthesisofSaturatedNitrogenHeterocyclesviaAlkene,Alkyne,
orAlleneAminopalladationReactions 3
1.3.1 PdII-CatalyzedOxidativeAminationofAlkenes 4
1.3.2 Pd-CatalyzedHydroaminationReactionsofAlkenesandAlkynes 6
1.3.3 Pd0-CatalyzedCarboaminationReactionsofAlkenes 8
1.3.4 PdII-CatalyzedCarboaminationReactionsofAlkenes 10
1.3.5 Pd-CatalyzedCarboaminationReactionsofAlkynes,Allenes,
andDienes 10
1.3.6 VicinalDifunctionalizationofAlkenesandAllenes 13
1.4 SynthesisofNitrogenHeterocyclesviaIntermediate
p-AllylpalladiumComplexes 16
1.4.1 ReactionsInvolvingOxidativeAdditionofAllylicElectrophiles 16
1.4.2 ReactionsInvolvingp-AllylpalladiumIntermediatesGenerated
viaAlkeneCarbopalladation 19
1.4.3 ReactionsInvolvingAminopalladationof1,3-Dienes 21
1.4.4 GenerationofAllylpalladiumIntermediatesthroughC–H
Activation 21
1.5 SynthesisofNitrogenHeterocyclesviaPd-Catalyzed
1,3-DipolarCycloadditionReactions 22
1.6 SynthesisofNitrogenHeterocyclesviaCarbonylativeProcesses 23
1.6.1 TransformationsInvolvingCOInsertionintoArylorAlkenylPd-Carbon
Bonds 23
VI Contents
1.6.2 TransformationsInvolvingCOInsertionIntoaPd–Heteroatom
Bond 25
1.6.3 Wacker-TypeCarbonylativeProcesses 26
1.7 SummaryandFutureOutlook 28
References 28
2 TransitionMetalCatalyzedApproachestoLactonesInvolvingC–O
BondFormation 35
CharlesS.Yeung,PeterK.Dornan,andVyM.Dong
2.1 Introduction 35
2.2 SynthesisofLactonesInvolvingCO 36
2.2.1 CarbonylationofC–XBonds 36
2.2.2 CarbonylationofC–MBonds 39
2.2.3 HydrocarbonylationofC¼CandC(cid:2)CBonds 40
2.2.4 CarbocarbonylationofC¼CandC(cid:2)CBonds 42
2.2.5 HeterocarbonylationofC¼CandC(cid:2)CBonds 43
2.2.6 MiscellaneousLactoneSynthesesInvolvingCO 45
2.3 SynthesisofLactonesviaC¼CandC(cid:2)CAddition 46
2.3.1 HydrocarboxylationofC¼CandC(cid:2)CBonds 46
2.3.2 Carbo-andOxy-CarboxylationofC¼CandC(cid:2)CBonds 50
2.4 SynthesisofLactonesviaC¼OHydroacylation 52
2.4.1 AldehydeHydroacylation 52
2.4.2 KetoneHydroacylation 53
2.4.3 [4 þ 2]Annulation 55
2.5 MiscellaneousSynthesesofLactones 56
2.5.1 OxidativeLactonizationofDiols 56
2.5.2 ReductiveCyclizationofKetoacidsandKetoesters 57
2.5.3 C–HOxygenation 58
2.5.4 RingClosureofBenzoicAcidswithDihaloalkanes 59
2.5.5 Baeyer–VilligerOxidationofCyclicKetones 60
2.5.6 RingOpeningofCyclopropaneswithCarboxylicAcids 60
2.5.7 RingClosureofo-IodobenzoateswithAldehydes 61
2.5.8 SynthesisofLactonesInvolvingCO 62
2
2.5.9 MichaelAdditionofa,b-UnsaturatedN-Acylpyrrolidines 62
2.5.10 [2 þ 2]CycloadditionofKetenesandAldehydes 63
2.5.11 TandemCross-Metathesis/HydrogenationRoutetoLactones 63
2.5.12 ModernCatalyticVariantsofClassicalMacrolactonizations 64
2.6 ConclusionsandOutlook 65
References 65
3 TheFormationofCsp2–SandCsp2–SeBondsbySubstitutionand
AdditionReactionsCatalyzedbyTransitionMetalComplexes 69
IrinaP.BeletskayaandValentineP.Ananikov
3.1 Introduction 69
3.2 CatalyticCross-CouplingReactions 70
Contents VII
3.2.1 Pd-CatalyzedTransformations 70
3.2.2 Ni-CatalyzedTransformations 77
3.2.3 Cu-CatalyzedTransformations 79
3.2.4 OtherTransitionMetalsasCatalysts 88
3.3 CatalyticAdditionofRZ–ZRDerivativestoAlkynes(Z(cid:2)S,Se) 90
3.3.1 PdandNi-CatalyzedFormationofVinylChalcogenides 90
3.3.2 Ni-CatalyzedSynthesisofDienes 100
3.3.3 Rh-CatalyzedReactions 101
3.3.4 CatalyticAdditionofS-XandSe-XBondstoAlkynes 102
3.3.5 CatalyticAdditiontoAllenes 103
3.4 CatalyticAdditionofRZ-HDerivativestoAlkynes(Z(cid:2)S,Se) 104
3.4.1 PdandNi-CatalyzedAdditionofThiolsandSelenols 104
3.4.2 RhandPt-CatalyzedAdditionofThiolstoAlkynes 109
3.4.3 CatalyticAdditionofThiolsandSelenolstoAllenes 111
3.5 Conclusions 112
References 113
4 PalladiumCatalysisforOxidative1,2-Difunctionalization
ofAlkenes 119
BéatriceJacquesandKilianMuñiz
4.1 Introduction 119
4.2 Palladium-Catalyzed1,2-DifunctionalizationReactions:
Halogenation 120
4.3 AminohalogenationReactions 121
4.4 Dialkoxylation 125
4.5 AminoacetoxylationReactions 127
4.6 DiaminationReactions 131
4.7 Conclusion 134
References 134
5 Rhodium-CatalyzedC–HAminations 137
HélèneLebel 137
5.1 MetalNitrenesfromIminoiodinanes 139
5.1.1 IntramolecularC–Hamination 140
5.1.2 IntermolecularC–HAminations 144
5.1.3 MechanismofC–HAminationusingHypervalentIodine
Reagents 147
5.2 MetalNitrenesfromN-Tosyloxycarbamates 149
References 154
6 ThePalladium-CatalyzedSynthesisofAromaticHeterocycles 157
YingdongLuandBruceA.Arndtsen
6.1 Introduction 157
6.2 Palladiump-LewisAcidity:IntramolecularNucleophilicAttack
onUnsaturatedBonds 159
VIII Contents
6.2.1 AdditiontoAlkynes 159
6.2.2 HeteroatomAdditiontoAlkyneswithFunctionalization 164
6.2.3 HeteroatomAdditiontoAllenes 168
6.2.4 HeteroatomAdditionstoAlkenes 171
6.3 Palladium-CatalyzedCarbon–HeteroatomBondForming
Reactions 174
6.3.1 Palladium-CatalyzedCarbon–NitrogenBondFormation 174
6.3.2 Palladium-CatalyzedCarbon–OxygenBondFormation 177
6.4 Palladium-CatalyzedCarbon–HeteroatomBondFormationwith
Alkynes 178
6.5 HeckCyclizations 182
6.6 PalladiumCatalyzedC–HBondActivation 185
6.7 MulticomponentCouplingReactions 189
6.8 SummaryandOutlook 194
References 194
7 NewReactionsofCopperAcetylides:CatalyticDipolarCycloadditions
andBeyond 199
ValeryV.Fokin
7.1 Introduction 199
7.2 Azide–AlkyneCycloaddition:Basics 200
7.3 Copper-CatalyzedCycloadditions 203
7.3.1 CatalystsandLigands 203
7.3.2 CuAACwithInSituGeneratedAzides 208
7.3.3 MechanisticaspectsoftheCuAACReaction 208
7.3.4 ReactionsofSulfonylAzides 215
7.3.5 SulfonylTriazolesasStableCarbenePrecursors 215
7.3.6 Reactionsof1-Iodoalkynes 218
7.3.7 ReactionsofCopperAcetylideswithOtherDipoles 220
References 221
8 TransitionMetal-CatalyzedSynthesisofMonocyclicFive-Membered
AromaticHeterocycles 227
AlexanderS.DudnikandVladimirGevorgyan
8.1 Introduction 227
8.2 MonocyclicFive-MemberedHeterocycles 228
8.2.1 Furans 228
8.2.1.1 SynthesisofFuransviaCycloisomerizationReactions 228
8.2.1.2 SynthesisofFuransvia‘‘3 þ 2’’CycloadditionReactions 264
8.2.2 Pyrroles 273
8.2.2.1 SynthesisofPyrrolesviaCycloisomerizationReactions 273
8.2.2.2 SynthesisofPyrrolesvia‘‘4 þ 1’’CycloadditionReactions 283
8.2.2.3 SynthesisofPyrrolesvia‘‘3 þ 2’’CycloadditionReactions 293
8.2.2.4 SynthesisofPyrrolesvia‘‘2 þ 2 þ 1’’Cycloaddition
Reactions 298