卤素-镁交换制备多官能团格氏试剂的研究进展

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351-201335127~31櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅櫅殯殯殯殯46-赵娟,万洪,谷玉杰,杜咏梅,吕剑*710065-、、。。-O621.25A0258-3283201301-0027-052012-05-172010K07-06。1988-。E-mailcanghaiyisu_zj@126.com。。1234。。-。1931Prévost-。。-、、、。、、1。1-、、。1.1。。4-1-20℃24-225℃3。-Preparationofarylmagnesiumreagentsfromiodine-magnesiumexchange-。344。572DOI:10.13822/j.cnki.hxsj.2013.01.00820131565。-Preparationofmagnesiumcompoundsbearinganitrofunction。R3MgLi-RMgX。14-7R3MgLi86。-Preparationofdi-Grignardreagentsfromiodine-magnesiumexchange---。5。5。-Preparationofarylmagnesiumreagentsfrombromine-magnesiumexchangeR3MgLi。9-107。-。1.2-。5。-。114-128。-Preparationoffunctionalizedheteroarylmagnesiumreagentsfromchlorine-magnesiumexchange。-8。1314159。-Selectivehalogen-magnesiumexchangeinpolyhalogenatedheterocycles、、-。Jaramillo1017-16。82351--Preparationofimportantintermediatesfromiodine-magnesiumexchange1.3-。。。5。18-50℃192011。-Preparationoffunctionalizedalkenylmagnesiumreagentsfrombromo-magnesiumexchange-12。2122。Y=CNSO2PhCO2t-BuCONEt2Preparationoffunctionalizedalkenylmagnesiumreagentsbearinganelectron-withdrawinggroup1.4、。-13。。23242513。Stereoselectivepreparationoffuctionalizedcyclopropylmagnesiumreagents-。C3H7I-2614。Preparationofperfluoroaliphaticmagnesiumreagents2-、、、。2.1。N-NMP5。27THFNMP288。NMP-Iodine-magnesiumexchangeproceedsinNMP2.29220131RI>RBr>RCl。5min1h15。。2.3。。16。2.4-。。。17。33.1、、、、、2-47811。3.25。3.2.1。Pd-catalyzedcross-couplingofhighlyfunctionalizedarylzincreagentsNiⅡ-catalyzedcross-couplingofhighlyfunctionalizedarylzincreagents。293130183219。。Dohle20333435。Cu-mediatedcross-couplingreactionsoffunctionalizedmagnesiumcompounds3.2.2。MgX+ArPdL2--。363721。Pd-catalyzedcross-couplingoffunctionalizedmagnesiumreagents384039224123。FeⅢ-catalyzedcross-couplingreactionswithfunctionalizedmagnesiumspecies03351-CoⅡ-catalyzedcross-couplingreactionswithfunctionalizedmagnesiumspecies4-。。。1ZIESSELR.Makingnewsupermoleculesforthenextcen-tury.multipurposereagentsfromethynyl-graftedoligopyri-dinesJ.Synthesis1999111839-1865.2JENSENAEDOHLEWSAPOUNTZISIetal.Prepara-tionandreactionsoffunctionalizedarylmagnesiumrea-gentsJ.Synthesis20024565-569.3CALIPBEGTRUPM.Synthesisofarylglycinesbyreac-tionofdiethylN-Boc-iminomalonatewithorganomagne-siumreagentsJ.Synthesis2002163-66.4SAPOUNTZISIKNOCHELP.Generalpreparationoffunctionalizedo-nitroarylmagnesiumhalidesthroughaniodine-magnesiumexchangeJ.Angew.Chem.20024191610-1611.5PAULKWOLFGANGDNINAGetal.Highlyfunc-tionalizedorganomagnesiumreagentspreparedthroughhalogen-metalJ.Angew.Chem.Int.Ed.2003424302-4320.6INOUEAKITAGAWAKSHINOKUBOHetal.Selec-tivehalogen-magnesiumexchangereactionviaorganomag-nesiumatecomplexJ.J.Org.Chem.200166124333-4339.7NISHIYAMAHISAKAKITOHKetal.Metal-halogenexchangebetweenpolybromoanisolesandaliphaticGri-gnardreagentsasynthesisofcyclopentabbenzofuransJ.J.Org.Chem.1992571407-410.8ABARBRIMTHIBONNETJBERILLONLetal.Prep-arationofnewpolyfunctionalmagnesiatedheterocyclesusingachlorine-bromine-oriodine-magnesiumexchangeJ.J.Org.Chem.200065154618-4634.9ABARBRIMDEHMELFKNOCHELP.Bromine-mag-nesium-exchangeasageneraltoolforthepreparationarylandheteroarylmagnesium-reagentsJ.TetrahedronLett.199940427449-7453.10JARAMILLOCCARRETEROJCDIEGOJEetal.Regioselectivesynthesisof36-disubstituted2-aminoim-idazo12-apyridinesJ.TetrahedronLett.200243509051-9054.11VUVAMAREKIKNOCHELP.Stereoselectiveprep-arationoffunctionalizedunsaturatedlactonesandesterviafunctionalizedmagnesiumcarbenoidsJ.Synthesis2003121797-1802.12THIBONNETJKNOCHELP.Preparationoffunctional-izedalkenylmagnesiumbromidesviaabromine-magnesi-umexchangeJ.TetrahedronLett.200041183319-3322.13VUVAMAREKIPOLBORNKetal.PreparationofnewfunctionalizedcyclopropylmagnesiumreagentsJ.Angew.Chem.Int.Ed.2002412351-352.14DENSONDDSMITHCFTAMBORSKIC.SynthesisofperfluoroaliphaticGrignardreagentsJ.J.Fluor.Chem.1973743247-258.15TAMBORSKICMOOREGJ.Synthesisofpolyfluoroar-omaticmagnesiumcompoundsthroughtheexchangereactionJ.J.Org.Chem.1971262153-156.16HAUKDLANGSMURSOA.Minimizationofsidereactionsinbrominemagnesiumexchangeswithi-PrMgCl/LiClands-BuMgCl/LiClmixturesJ.Org.Pro.Res.&Develop.2006104733-738.17TANGWen-junSARVESTANIMWEIXu-dongetal.Formationof2-trifluoromethylphenylGrignardreagentviamagnesium-halogenexchangeprocesssafetyevalua-tionandconcentrationeffectJ.OrganicProcessRe-search&Development20091361426-1430.18JENSENAEKNOCHELP.Preparationof2-arylated-14-phenylenediaminesbypalladium-catalyzedcross-couplingreactionsJ.J.Org.Chem.20026531/2122-128.19GIOVANNINIRSTUEDEMANNTDEVASAGAY-ARAJAetal.Newefficientnickel-catalyzedcross-cou-plingreactionbetweentwoCsp3centersJ.J.Org.Chem.199964103544-3553.20DOHLEWLINDSAYDMKNOCHELP.Copper-me-diatedcross-couplingoffunctionalizedarylmagnesiumreagentswithfunctionalizedalkylandbenzylichalidesJ.Org.Lett.20013182871-2873.(下转第46页)13201316Tab.6Resultofmicrowaveashingrepeatabilitytests%n=7RSD40.0890.0960.0870.0790.0970.0910.0840.0897.950.1030.0950.0970.1030.1020.0920.1010.0994.060.0900.0940.0960.0900.0850.0840.0920.0904.4T=900℃。3、。650℃2h。900℃Fe、Ni、SnV。。1.TLAJ.201037-8.2SH/T0422—2000S.2000.3T0614—1993S.1993.4ASTMD487—03S.2003.5ASTMD2415—19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