Amination and Formation of sp2 C-N Bonds

214 Pages·2013·7.72 MB·English

by  Georgia S. Lemen

Topics in Organometallic Chemistry 46
Marc Taillefer
Dawei Ma Editors
Amination and
Formation of sp2
C–N Bonds
46
Topics in Organometallic Chemistry
Editorial Board:
M. Beller J. M. Brown P. H. Dixneuf
l l
J. Dupont A. Fu¨rstner L. J. Gooßen
l l
P. Hofmann T. Ikariya S. Nolan
l l
L. A. Oro Q.-L. Zhou
l
Topics in Organometallic Chemistry
Recently Published Volumes
Alkaline-EarthMetalCompounds: HigherOxidationStateOrganopalladium
OdditiesandApplications andPlatinumChemistry
VolumeEditor:SjoerdHarder VolumeEditor:A.J.Canty
Vol.45,2013 Vol.35,2011
InventingReactions IridiumCatalysis
VolumeEditor:LukasJ.Gooßen VolumeEditor:P.G.Andersson
Vol.44,2013 Vol.34,2011
IronCatalysis–Fundamentalsand
Hydrofunctionalization
Applications
VolumeEditors:ValentineP.Ananikov,
VolumeEditor:B.Plietker
MasatoTanaka
Vol.33,2011
Vol.43,2013
MedicinalOrganometallicChemistry
OrganometallicsasCatalysts
VolumeEditors:G.Jaouen,N.Metzler-Nolte
intheFineChemicalIndustry
Vol.32,2010
VolumeEditors:MatthiasBeller,
Hans-UlrichBlaser C-XBondFormation
Vol.42,2012 VolumeEditor:A.Vigalok
Vol.31,2010
ModernOrganoaluminumReagents:
TransitionMetalComplexesofNeutral
Preparation,Structure,ReactivityandUse
h1-CarbonLigands
VolumeEditors:SimonWoodward,
VolumeEditors:R.Chauvin,Y.Canac
SamuelDagorne
Vol.30,2010
Vol.41,2012
PhotophysicsofOrganometallics
OrganometallicPincerChemistry
VolumeEditor:A.J.Lees
VolumeEditors:GerardvanKoten,
Vol.29,2010
DavidMilstein
Vol.40,2012 MolecularOrganometallicMaterials
forOptics
OrganometallicsandRenewables VolumeEditors:H.LeBozec,V.Guerchais
VolumeEditors:MichaelA.R.Meier, Vol.28,2010
BertM.Weckhuysen,PieterC.A.Bruijnincx
ConductingandMagneticOrganometallic
Vol.39,2012
MolecularMaterials
TransitionMetalCatalyzedEnantioselective VolumeEditors:M.Fourmigue´,L.Ouahab
AllylicSubstitutioninOrganicSynthesis Vol.27,2009
VolumeEditor:UliKazmaier
MetalCatalystsinOlefinPolymerization
Vol.38,2011
VolumeEditor:Z.Guan
BifunctionalMolecularCatalysis Vol.26,2009
VolumeEditors:T.Ikariya,M.Shibasaki Bio-inspiredCatalysts
Vol.37,2011 VolumeEditor:T.R.Ward
Vol.25,2009
AsymmetricCatalysisfromaChinese
Perspective DirectedMetallation
VolumeEditor:ShengmingMa VolumeEditor:N.Chatani
Vol.36,2011 Vol.24,2007
Amination and Formation
2
of sp C–N Bonds
Volume Editors: Marc Taillefer and Dawei Ma
With Contributions by
(cid:1) (cid:1) (cid:1) (cid:1)
C. Bolm S. Bhargava A. Correa Y. Jiang
(cid:1) (cid:1) (cid:1) (cid:1)
M.L. Kantam G.S. Lemen D. Ma F. Monnier
(cid:1) (cid:1) (cid:1)
C. Venkat Reddy P. Srinivas M. Taillefer J.P. Wolfe
Editors
MarcTaillefer DaweiMa
EcoleNationaleSuperieuredeChimie ShanghaiInstituteofOrganicChemistry
(CNRS) ChineseAcademyofSciences
Montpellier Shanghai
France People’sRepublicofChina
ISSN1436-6002 ISSN1616-8534(electronic)
ISBN978-3-642-40545-7 ISBN978-3-642-40546-4(eBook)
DOI10.1007/978-3-642-40546-4
SpringerHeidelbergNewYorkDordrechtLondon
LibraryofCongressControlNumber:2013956808
#Springer-VerlagBerlinHeidelberg2013
Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof
the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations,
recitation,broadcasting,reproductiononmicrofilmsorinanyotherphysicalway,andtransmissionor
informationstorageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilar
methodologynowknownorhereafterdeveloped.Exemptedfromthislegalreservationarebriefexcerpts
inconnectionwithreviewsorscholarlyanalysisormaterialsuppliedspecificallyforthepurposeofbeing
enteredandexecutedonacomputersystem,forexclusiveusebythepurchaserofthework.Duplication
ofthispublicationorpartsthereofispermittedonlyundertheprovisionsoftheCopyrightLawofthe
Publisher’s location, in its current version, and permission for use must always be obtained from
Springer.PermissionsforusemaybeobtainedthroughRightsLinkattheCopyrightClearanceCenter.
ViolationsareliabletoprosecutionundertherespectiveCopyrightLaw.
Theuseofgeneraldescriptivenames,registerednames,trademarks,servicemarks,etc.inthispublication
doesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexemptfromtherelevant
protectivelawsandregulationsandthereforefreeforgeneraluse.
Whiletheadviceandinformationinthisbookarebelievedtobetrueandaccurateatthedateofpublication,
neithertheauthorsnortheeditorsnorthepublishercanacceptanylegalresponsibilityforanyerrorsor
omissionsthatmaybemade.Thepublishermakesnowarranty,expressorimplied,withrespecttothe
materialcontainedherein.
Printedonacid-freepaper
SpringerispartofSpringerScience+BusinessMedia(www.springer.com)
Preface
Theuseoftransitionmetalcatalysishasprovidedorganicchemistswithawideand
quasi-exhaustive toolbox to create selectively the C(sp2)-N bonds, essential not
onlyforthedevelopmentofbioactivemoleculesbutalsoformaterialsengineering.
Drawing on the bountiful number of publications related to this topic in the last
10years,thisvolumemainlyfocusesonthemostsignificantresultsandimportant
breakthroughs.
The volume highlights in the first chapter, written by Lemen and Wolfe, the
discoveryandthedevelopmentoforiginalpalladium-basedcatalystsforC(sp2)-N
bondformationvia thecoupling ofnitrogennucleophilesandaryl/alkenylhalides
and pseudohalides. The authors also report various applications of these transfor-
mationstothesynthesisofusefulcompounds,includingbiologicallyactivemole-
culesandmaterials.
In the second chapter, Correa and Bolm discuss a powerful set of protocols
involvingC(sp2)-Nbondformationwhichhaveemergedasreliableandconvenient
alternativesfortheassemblyofenaminesandenamides.Theauthorsalsodescribe
palladium-catalyzed oxidative amination of alkenes and both palladium- and
copper-catalyzedcross-couplingsgenerallybetweenvinylhalidesorpseudohalides
andaminesoramides.
Owing to their importance for pharmaceutical and material sciences,
N-containing heterocycles have received great attention from the synthetic com-
munity. Another masterpiece of this volume “Assembly of N-Containing Hetero-
cycles via Pd and Cu-Catalyzed C–N Bond Formation Reactions”, presented by
JiangandMa,coverstheoriginalandlastcontributionsonthedevelopmentofPd-
and Cu-catalysts for the assembly of N-heterocycles such as indoles, benzimida-
zoles, pyrroles, indazoles, indolines, lactams, quizolinones, heterobenzazepines,
andotherN-containingheterocycles.
By far the greatest number of reports on the modern catalytic Ullmann-type
reactionshasdealtwiththecreationofC–Nbonds.Kantametal.present,intheir
chapter, the recent developments in heterogeneous or recyclable copper-catalysts
availabletoselectivelyformthisC(sp2)-Nbond.Thechallengesandopportunities
v
vi Preface
incopper-catalyzedheterogeneouscatalysisareenormousaslessresearchhasbeen
carried out in this area compared to homogeneous systems. This part covers the
recentrecyclableprotocolsfortheC(cid:3)Nbondformingreactionsbetweenaromatic,
heterocyclic, and aliphatic-amines with aryl iodides, bromides, chlorides, and
arylboronicacidsemployingcoppermediatedsystems.
The last chapter by Monnier and Taillefer focuses on the copper-catalyzed
formation of C(sp2)-N bond via the coupling of nitrogen nucleophiles
(N-heterocycles, amines, anilines, amides, ammonia, azides, hydroxylamines,
nitrites salts, phosphonic amides) with aryl halides. The authors also present C
(aryl)–Nbondformationasaresultofthecouplingbetweenthesenucleophilesand
aryl-boronicacids(theChan–Lamreaction).
Wewouldliketothanktheauthorsfortheirdiligentworkonthishottopic.
Montpellier,France MarcTaillefer
Shanghai,China DaweiMa
Contents
Palladium-Catalyzedsp2C–NBondFormingReactions:Recent
DevelopmentsandApplications ............................................... 1
GeorgiaS.LemenandJohnP.Wolfe
Metal-CatalyzedC(sp2)–NBondFormation ................................ 55
ArkaitzCorreaandCarstenBolm
AssemblyofN-ContainingHeterocyclesviaPd-andCu-Catalyzed
C–NBondFormationReactions ............................................. 87
YongwenJiangandDaweiMa
RecentDevelopmentsinRecyclableCopperCatalystSystems
forC–NBondFormingCross-CouplingReactionsUsing
ArylHalidesandArylboronicAcids ........................................ 119
MannepalliLakshmiKantam,ChintareddyVenkatReddy,
PottabathulaSrinivas,andSureshBhargava
Copper-CatalyzedC(aryl)–NBondFormation ............................ 173
FlorianMonnierandMarcTaillefer
Index .......................................................................... 205
vii
TopOrganometChem(2013)46:1–54
DOI:10.1007/3418_2012_56
#Springer-VerlagBerlinHeidelberg2012
Publishedonline:13February2013
Palladium-Catalyzed sp2 C–N Bond Forming
Reactions: Recent Developments
and Applications
GeorgiaS.LemenandJohnP.Wolfe
Abstract ThisreviewdescribesrecentdevelopmentsinthefieldofPd-catalyzedsp2
C–Nbondformationthatwerereportedintheprimaryliteraturebetween2004and
2008. These transformations have found widespread application in both academia
andindustry.Abriefhistoryofthefieldispresented,followedbyrecentimprovements
and extensions of the methodology. Applications of these transformations to the
synthesisofusefulcompounds,includingbiologicallyactivemolecules,andmaterials,
aredescribed.
Keywords Arylamines(cid:1)Cross-coupling(cid:1)Heterocycles(cid:1)Materials(cid:1)N-Arylation(cid:1)
Naturalproducts
Contents
1 IntroductionandScope....................................................................... 2
2 EarlyWorkPriorto2004.................................................................... 2
3 ImprovementsandExtensionsofPd-CatalyzedN-ArylationMethods.................... 6
3.1 NewLigandsandContinuedExploration
ofExistingLigands..................................................................... 6
3.2 ModifiedReactionConditionsorTechniquesThatFacilitatePd-Catalyzed
N-Arylations............................................................................ 13
3.3 NewNucleophilesandElectrophilesorImprovedReactionsofPreviously
StudiedNucleophilesandElectrophiles............................................... 13
4 Applications.................................................................................. 24
4.1 SynthesisofHeterocyclesviaReactionSequencesInvolvingN-Arylation.......... 24
4.2 SynthesisofNaturalProductsandPharmaceuticalTargetMolecules............... 27
4.3 SynthesisofMoleculeswithPotentialMaterialsChemistryApplications........... 30
4.4 UseofN-ArylationReactionsfortheSynthesisofLigandsforMetalComplexesand
Catalysts................................................................................ 38
4.5 ProcessScaleApplicationsofPd-CatalyzedN-ArylationReactions................. 40
5 Conclusion.................................................................................... 42
References........................................................................................ 42
G.S.LemenandJ.P.Wolfe(*)
DepartmentofChemistry,UniversityofMichigan,AnnArbor,MI48109-1055,USA
e-mail:[email protected]
2 G.S.LemenandJ.P.Wolfe
Abbreviations
mW Microwave
Cy Cyclohexyl
Dba Dibenzylideneacetone
Dppe 1,2-Bis(diphenylphosphinoethane)
Dppp 1,3-Bis(diphenylphosphinopropane)
Hex n-Hexyl
HMDS Hexamethyldisilazide
IPr N,N0-Bis(2,6-diisopropylphenyl)imadalol-2-ylidene
i-Pr Isopropyl
PMP 4-Methoxyphenyl
SAR Structure–activityrelationship
TBS tert-Butyldimethylsilyl
1 Introduction and Scope
MoleculesthatcontainarylC–Nbondsplayimportantrolesinmanydifferentareasof
chemistry,includingmaterialsandpharmaceuticals.Forexample,anumberoftop-
sellingdrugs,includingLipitor[1],Abilify[2],andCelebrex[3],containthisfunc-
tional unit. Over the past 15 years, Pd-catalyzed coupling reactions between aryl
halidesandamineshavedevelopedintobroadlyutilizedmethodsforsp2C–Nbond
formation.Thesetransformationshavebeenusedonbothsmallacademicscalesand
verylargeindustrialscales.Duetothesignificanceofthisfield,anumberofreviews
havebeenpreviouslypublisheddescribingvariousstagesofitsdevelopment([4–11];
foracomprehensivereviewontheBuchwaldbiarylphosphineligands,see[12];fora
reviewontheutilityofJosiphos-typeligandsinPd-catalyzedN-arylationreactions,
see [13];[14–21]). Thisreviewoutlines key aspects ofPd-catalyzedsp2 C–Nbond
formingcross-couplingreactionsofnitrogennucleophilesandaryl/alkenylhalidesand
pseudohalidesthatwerereportedintheliteraturebetween2004and2008.Although
this review is focused primarily on synthetic aspects of the chemistry, a very brief
descriptionofreactionmechanismalongwithabriefhistoricalbackgroundisprovided
toplacethecurrentworkincontextandaidthereader.
2 Early Work Prior to 2004
The first example ofthe formationofan aryl C–N bond via a Pd-catalyzed cross-
couplingreactionofanarylhalidewasreportedin1983byMigitaandcoworkers
[22,23].Duringthecourseoftheirstudiesonthereactivityoforganotincompounds,