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Buchwald-HartwigCrossCouplingReaction

Palladium-catalyzedsynthesisofarylamines.Startingmaterialsarearylhalidesorpseudohalides(forexampletriflates)andprimaryorsecondaryamines.

ThesynthesisofarylethersandespeciallydiarylethershasrecentlyreceivedmuchattentionasanalternativetotheHYPERLINK"http://www.organic-chemistry.org/namedreactions/ullmann-reaction.shtm"UllmannEtherSynthesis.
Newercatalystsandmethodsofferabroadspectrumofinterestingconversions.

MechanismoftheBuchwald-HartwigCoupling

RecentLiterature
[(CyPF-tBu)PdCl2]:AnAir-Stable,One-Component,HighlyEfficientCatalystforAminationofHeteroarylandArylHalidesQ.Sheng,J.F.Hartwig,Org.Lett.,2008,10,4109-4112.
AMultiligandBasedPdCatalystforC-NCross-CouplingReactionsB.P.Fors,S.L.Buchwald,J.Am.Chem.Soc.,2010,132,15914-15917.
Palladium-CatalyzedCouplingofAmmoniawithArylChlorides,Bromides,Iodides,andSulfonates:AGeneralMethodforthePreparationofPrimaryArylaminesG.D.Vo,J.F.Hartwig,J.Am.Chem.Soc.,2009,131,11049-11061.
(IPr)Pd(acac)Cl:AnEasilySynthesized,Efficient,andVersatilePrecatalystforC-NandC-CBondFormationN.Marion,E.C.Ecarnot,O.Navarro,D.Amoroso,A.Bell,S.P.Nolan,J.Org.Chem.,2006,71,3816-3821.
SynthesisofBulkyandElectron-RichMOP-typeLigandsandTheirApplicationsinPalladium-CatalyzedC-NBondFormationX.Xie,T.Y.Zhang,Z.Zhang,J.Org.Chem.,2006,71,6522-6529.
Triazole-BasedMonophosphineLigandsforPalladium-CatalyzedCross-CouplingReactionsofArylChloridesQ.Dai,W.Gao,D.Liu,L.M.Kapes,X.Zhang,J.Org.Chem.,2006,71,3928-3934.
BulkyAlkylphosphineswithNeopentylSubstituentsasLigandsintheAminationofArylBromidesandChloridesL.L.Hill,L.R.Moore,R.Huang,R.Craciun,A.J.Vincent,D.A.Dixon,J.Chou,C.J.Woltermann,K.H.Shaughnessy,J.Org.Chem.,2006,71,4951-4955.
Water-MediatedCatalystPreactivation:AnEfficientProtocolforC-NCross-CouplingReactionsB.P.Fors,P.Krattiger,E.Strieter,S.L.Buchwald,Org.Lett.,2008,10,3505-3508.
AHighlyActiveCatalystforPd-CatalyzedAminationReactions:Cross-CouplingReactionsUsingArylMesylatesandtheHighlySelectiveMonoarylationofPrimaryAmines