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1、ReviewsK.C.Nicolaouetal.SyntheticMethodsPalladium-CatalyzedCross-CouplingReactionsinTotalSynthesisK.C.Nicolaou,*PaulG.Bulger,andDavidSarlahKeywords:DedicatedtoRichardF.HeckCCcoupling·cross-coupling·ontheoccasionofhis74thbirthdaypalladiumcatalysis·syntheticmethods·totalsynthesisA
2、ngewandteChemie44422005Wiley-VCHVerlagGmbH&Co.KGaA,WeinheimDOI:10.1002/anie.200500368Angew.Chem.Int.Ed.2005,44,4442–4489AngewandteCCCouplingChemieInstudyingtheevolutionoforganicchemistryandgraspingitsFromtheContentsessence,onecomesquicklytotheconclusionthatnoothertypeof1.Introd
3、uction4443reactionplaysaslargearoleinshapingthisdomainofsciencethancarbon–carbonbond-formingreactions.TheGrignard,2.TheHeckReaction4445Diels–Alder,andWittigreactionsarebutthreeprominentexam-plesofsuchprocesses,andareamongthosewhichhaveundeni-3.TheStilleReaction4452ablyexercisedde
4、cisiverolesinthelastcenturyintheemergenceof4.TheSuzukiReaction4458chemicalsynthesisasweknowittoday.Inthelastquarterofthe20thcentury,anewfamilyofcarbon–carbonbond-forming5.TheSonogashiraReaction4468reactionsbasedontransition-metalcatalystsevolvedaspowerfultoolsinsynthesis.Amongthe
5、m,thepalladium-catalyzedcross-6.TheTsuji–TrostReaction4473couplingreactionsarethemostprominent.InthisReview,high-7.TheNegishiReaction4478lightsofanumberofselectedsynthesesarediscussed.Theexampleschosendemonstratetheenormouspowerofthese8.SummaryandOutlook4481processesintheartoftot
6、alsynthesisandunderscoretheirfuturepotentialinchemicalsynthesis.1.Introductionformallyresultfromthesubstitutionofahydrogenatominthealkenecouplingpartner.ThefirstexamplesofthisEversincethefirstlaboratoryconstructionofacarbon–reactionaswewouldrecognizeittodaywerereported[2]carbonbo
7、ndbyKolbeinhishistoricsynthesisofaceticacidinindependentlybyMizoroki(1971)and,inanimproved[3]1845,carbon–carbonbond-formingreactionshaveplayedanform,byHeck(1972).However,itwouldprovetobemoreenormouslydecisiveandimportantroleinshapingchemicalthanadecadebeforethebroaderapplicabilit
8、yofthissynthesis.Aldol-andGrignard-typer
