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Heck反应合成几种吲哚衍生物的研究的综述报告.docx

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Heck反应合成几种吲哚衍生物的研究的综述报告 Introduction TheHeckreactionisapowerfulsynthetictoolthatinvolvesthepalladium-catalyzedcouplingofanarylorvinylhalidewithanunsaturatedcarbon-carbonbond.ThereactionwasfirstreportedbyTsutomuMizorokiandRichardHeckin1972,andsincethenithasbeenwidelyusedinorganicsynthesisfortheconstructionofcarbon-carbonbonds.Inparticular,theHeckreactionisknowntobeanefficientmethodforthesynthesisofindolederivatives.ThisreviewwillcoverrecentprogressintheapplicationoftheHeckreactionforthesynthesisofindolederivatives. HeckReactionfortheSynthesisofIndoleDerivatives Indoleisaheterocycliccompoundthatiswidelyfoundinnaturalproducts.Indoleanditsderivativeshaveattractedconsiderableattentionduetotheirbiologicalactivitiesandsyntheticpotential.Thepalladium-catalyzedHeckreactionhasbeenshowntobeanefficientmethodforthesynthesisofindolederivatives.Ingeneral,thereactioninvolvesthecouplingofarylorvinylhalideswithunsaturatedcarbon-carbonbondsinthepresenceofapalladiumcatalystandabase. OneoftheearliestexamplesoftheHeckreactionforthesynthesisofindolederivativeswasreportedbyMizorokietal.Theyused2-bromoanilineasasubstrateand1-methyl-2-methyleneindoleasthecouplingpartnerinthepresenceofPd(PPh3)4andtriethylamineasthebase.ThereactiongavethecorrespondingN-arylindoleingoodyield(Scheme1). Scheme1.Mizoroki-HeckreactionforthesynthesisofN-arylindole. Sincethen,numerousexamplesoftheHeckreactionforthesynthesisofindolederivativeshavebeenreported.Thesereactionscanbeclassifiedintotwomaintypes:theC2-arylationofindoleandtheN-arylationofindole.TheC2-arylationofindoleinvolvesthecouplingofanarylorvinylhalidewiththeC2-positionofindole(Scheme2),whereastheN-arylationofindoleinvolvesthecouplingofanarylorvinylhalidewiththenitrogenatomofindole(Scheme3). Scheme2.C2-arylationofindole. Scheme3.N-arylationofindole. Ingeneral,theC2-arylationofindoleisthemorecommontypeofHeckreactionforthesynthesisofindolederivatives.ThisisduetothefactthattheC2-positionofindoleiselectron-rich,makingitmorereactivetowardspalladium-catalyzedco