钯催化negishi交叉偶联芳基氯乙烯一种通用方法使用市售pdpt-2001 the first general medai一届.pdfVIP

J.Am.Chem.Soc.2001,1232719

TheFirstGeneralMethodforPalladium-CatalyzedNegishi

Cross-CouplingofArylandVinylChlorides:UseofCommercially

AvailablePd(P(t-Bu))asaCatalyst

32

ChaoyangDaiandGregoryC.Fu*

ContributionfromtheDepartmentofChemistry,MassachusettsInstituteofTechnology,

Cambridge,Massachusetts02139

ReceiedNoember14,2000

:Withasingleprotocol,commerciallyavailablePd(P(t-Bu))caneffecttheNegishicross-coupling

32

ofawiderangeofarylandvinylchlorideswitharyl-andalkylzincreagents.Theprocesstoleratesnitro

groups,anditefficientlygeneratesstericallyhinderedbiaryls.Inaddition,ahighturnovernumber(3000)

canbeachieved.

Introductionhowever,therehavebeenonlyisolatedinstancesofpalladium-

catalyzedNegishireactionsofarylchlorides,15althoughmethods

Thepalladium-catalyzedcross-couplingofarylandvinyl

1forthecorrespondingnickel-catalyzedprocesshavebeen

halides/triflateswithorganozincreagents(Negishireaction)described.16,17Inthisreport,weestablishthatcommercially

representsapowerfulmethodforgeneratingaromaticcom-

poundssuchasstyrenederivativesandbiaryls,whichare(9)Forearlyexamples,see:(a)Old,D.W.;Wolfe,J.P.;Buchwald,S.

importantsynthetictargetsindisciplinesrangingfrommaterialsL.J.Am.Chem.Soc.1998,120Wolfe,J.P.;Singer,R.A.;

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