Cu催化碳碳偶联反应

Cu-catalyzedc-cbondcouplingreactionCouplingreactionClassification：Homocouplingreaction，Cross-couplingreactionCatalystsincommonuse：Na,Pd,Cu,Ni,etc.TheadvantageofCu-catalystCopperischeaperthanothercatalystssuchasPdPtNiandsoonTheconditionsoftheCu-catalystreactionismildandeasytogetCu-catalystsaremoreenvironmentallyfriendlyCu-catalyzedcouplingreactionGlaserreactionUllmannreactionCadiot-ChodkiewiczreactionCastro-StephensreactionSonogashirareactionOtherreactions一、GlaserreactionTags:1869,CuCl,sp-sp,aryneHaycouplingreaction：ChangethebaseNH4OHintoTMEDA，socanenhancethedissolvabilityinorganicsolvents，andincreasethekindsofsolvents.Eglintoncouplingreaction：UseCu(II)insteadofCu(I),suchasCupricacetate,andreplacethebasewithpyridineorotherorganicamines二、UllmannreactionTags:1903,Cu(0),sp2,aromatichalides三、Cadiot-ChodkiewiczreactionTags:1957,CuBr,Base,sp-sp,alkyne,Mechanism四、Castro-StephensreactionTags:1963,Cuprousacetylide,aromatichalides,sp-sp2,五、SonogashirareactionTags:1973,halogenatedetheneandarene,terminalalkynes,Pd,CuCl,sp-sp2J.Org.Chem.2008,73,9061–90649061六、Otherreactions1、sp-sp3Z.Lietal./Tetrahedron:Asymmetry17(2006)590–5972、sp2-sp3J.Org.Chem.1994,59,4126-4130Org.Lett.,Vol.12,No.10,20103、sp3-sp3J.Org.Chem.2008,73,7822–78254、sp2+CO2Reference唐金玉，江焕峰等，Glaser偶联反应研究进展[J]，有机化学，2005，,2(12)，1503-1507潘元佳，铜催化的Ullmann反应研究进展评介[J]，化工之友，2007,12,44-45Li,Z.P.MacLeod,P.D.Li,C.J.StudiesonCu-catalyzedasymmetricalkynylationoftetrahydroisoquinolinederivatives[J],Tetrahedron:Asymmetry17(2006)590–597Ohmiya,H.Yokokawa,N,Copper-Catalyzedγ-SelectiveandStereospecificAllylArylCouplingbetween(Z)-AcyclicandCyclicAllylicPhosphatesandArylboronates[J],Org.Lett.,2010,12(10),2438-2440Borduas,N.Powell,D.A.Copper-CatalyzedOxidativeCouplingofBenzylicC-HBondswith1,3-DicarbonylCompounds[J],J.Org.Chem.2008,19(73),7821-7824Blckvall,J.E.Persson,E.S.MRegiocontrolinCopper-CatalyzedCrossCouplingofAllylicChlorideswithArylGrignardReagents[J],J.Org.Chem.1994,59,4126-4130Huang,H.Jiang,H.L.EfficientIron/CopperCocatalyzedAlkynylationofArylIodideswithTerminalAlkynes,[J].J.Org.Chem.2008,73,9061–9064Li,Z.P.Li,C.J.CuBr-CatalyzedEfficientAlkynylationofsp3C-HBondsAdjacenttoaNitrogenAtom,[J].J.AM.CHEM.SOC.2004,126,11810-11811Zhang,Y.M.Fu,H.Copper-CatalyzedAmidationofsp3C−HBondsAdjacenttoaNitrogenAtom[J].Org.Lett.,2007,9(19),3814-3817Dang,L.Lin,Z.Y.DFTStudiesontheCarboxylationofArylboronateEsterswithCO2CatalyzedbyCopper(I)Complexes,[J]Organometallics.2010,29(4),917-927Thankyou!