三苯基膦及其衍生物的合成及应用

,(,100081):,:;;;:O625:A:0253-4320(2006)06-0066-04SynthesisandapplicationoftriphenylphosphineanditsderivatesWANGShu2bo,WANGLi2sheng(SchoolofChemicalandEnvironmentEngineering,BeijingInstituteofTechnology,Beijing100081,China)Abstract:Therecentdevelopmentofsynthesisandapplicationoftriphenylphosphineanditsderivatesarereviewedinthispaper.Itisshownthattriphenylphosphineanditsderivatesplayanimportantroleinorganicsynthesis,whichareprimarilyusedasintermediatesoforganicphosphorusflameretardantsandphosphorusligandsinbiphasicwatersolublecatalysts.Keywords:triphenylphosphine;triphenylphosphinederivates;synthesis;application:2006-02-19:(1964-),,;(1953-),,,,,,,010-68912660,[e-mail](PPh3)13,53d,166,(R3P)(POPS),/,,/,,-,(SAP),[1],,,(280),,,1111PPh3,PPh3Friedel-Crafts,,PPh3,,(TPPO),Friedel-CraftsPPh3,(Ph3PS),PPh3[2],,,,,,PPh39910%,66June2006266ModernChemicalIndustry20066©1994-2007ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.[3],,,PPh3,Allen[4]K2CO3Cs2CO3,CuI,,112,(TPPTS)(PETAPO)(4-)(THPPO)(4-)(BMPPO)(4-)(BCPPO)/(TPPMS)(TPPDS)TPPTS,(TPP)[5],TPPSO3,,,,Herd[6](FC6H4SO3K)(DMSO/KOH)ArnPH3-nCaron[7](CH3)3CC6H4MgBr[ClP(C6H5)2](Cl2PC6H5),,,Gulyas[8],,,,,,,(PETAPO)1-,PETAPO(4-)(THPPO)1,4-,,2hPETAPO,PETAPO-Ru1-,[9](4-)(THPPO)THPPO3,,,(UL94V-0)THPPO:,PCl3,HCl,,,(4-)(TMOPP);,TMOPPKMnO4,16h,,,(4-)(TMOPPO);-78,BBr3TMOPPOCH2Cl224h,,,THPPO[10](4-)(BCPPO)6,6,Wang[11],BCPPOPET,FR-PETBCPPO(4-)(BMPPS)(DCPPS)AlCl31212111BMPPS,BMPPS,;KOH,90KMnO46h;HCl,BCPPO,,,,Delaviz[12](4-)[4-(m-)](m-BAPPO)m-BAPPO,,220254,5%496557,7505%35%,,Zhang[13][4-(2-)](p-BAPPO),(4-)1,2-,p-BAPPO7620066:©1994-2007ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.(PPh3)nX(n=1,2,3;X=Cl,Br,I),,KXAgXNH4X,Ag(PPh3)nX,,,[14]TPP[Pd(PPh3)4][Pd(PPh3)2C6H4(CO)2NH][RuCl2(CO)2(PPh3)2RuCl2(PPh3)3[HRh(PPh3)3(CO)],salen,Kerrigan[15],salen,,,salen,(3,5-)93%,Ph3PX(X=O,S,Se),(TPPO),,,TPPOTPP[16]Kuntz[17],,,-,(TPPMSTPPDSTPPTS)RhTPPTSHRh(CO)4,3TPPTSHRh(CO)43CO,[HRh(CO)(TPPTS)3]SiO2,,-,Rh,;;,[HRh(CO)(TPPTS)3](TTP),1050,[HRh(CO)(TPPTS)n(TPP)3-n](n=03),[Rh(COD)Cl]2/TPPTS1-,,,TPP,TPP,,TPPTSPbCl2,CO,/Ru3(CO)9(TPPTS)3/CO,Wei[18],Ru/TPPTS,,,,3,/-,,,,86266©1994-2007ChinaAcademicJournalElectronicPublishingHouse.Allrightsreserved.()[19],Yavari[20]PPh3,(1-2-),PPh3Cl2,p-BCPPOm-BAPPO,,,3,,,,,-,[1]ArstadE,BarrettAGM,TedeschiL.ROMPgel2supportedtris(triph2enylphosphine)rhodium()chloride:aselectivehydrogenationcatalystforparallelsynthesis[J].TetraLett,2003,44:2703-2707.[2],,.[J].,2002,32(4):53-54.[3],,.[J].,1998,27:190-193.[4]AllenDV,VenkataramanD.Copper2catalyzedsynthesisofunsymmetri2caltriarylphosphines[J].JOrgChem,2003,68,4590-4593.[5],,,.(TPPTS)[J].,2000,14(3):223-226.[6]HerdO,LanghansKP,StelzerO,etal.Anewroutetowater2solublephosphaneswithpara2sulfonatedphenylsubstituents.CrystalstructureofP(C6H42p2SO3K)3KCl015H2O[J].AngewChemIntEdEngl,1993,32(7):1058-1059.[7]CaronL,CanipelleM,TilloyS,etal.Convenientsynthesisofnewam2phiphilictriphenylphosphineanaloguesforaqueousbiphasiccatalysis[J].TetraLett,2001,42:8837-8840.[8]GulyasH,SzollosyA,HansonBE,etal.Adirectapproachtoselectivesulfonationoftriarylphosphines[J].TetraLett,2002,43:2543-2546.[9]CornilsB.Fluorousbiphasesystems2thenewphase2separationandim2mobilizationtechnique[J].AngewChemIntEdEng,1997,36(19):2057-2059.[10]FriedrichsenBP,PowellDR,WhitlockHW.Stericallyencumberedfunctionalgroups:aninvestigationofendoversusexophosphorylcom2plexationusingprotonandphosphorus231NMR[J].JAmChemSoc,1990,112(24):8931-8941.[11]WangLS,WangXL,YanGL.Synthesis,characterisationandfamere2tardancebehaviourofpoly(ethyleneterephthalate)copolymercontainingtriarylphosphineoxide[J].PolymerDegradationandStability,2000,69:127-130.[12]DelavizY,GungorA,McGrathJE,etal.Solublephosphineoxidecon2tainingaromaticpolyamides[J].Polymer,1993,34(1):210-213.[13]ZhangY,TebbyJC,WheelerJW.Polyamidesincorporatingphosphineoxidegroups:Polymerisationofbis[42(22aminoethyl)aminophenyl]2phenylphosphineoxidewithdicarboxylicacids[J].JPolymSciPartA:PolymChem,2000,35(14):2865-2870.[14],,,.Ag(PPh3)nX(n=1,2,3;X=Cl,Br,I)[J].,2003,30(8):788-790.[15]KerriganNJ,LanganIJ,DaltonCT,etal.Asymmetricalkeneepoxida2tionwithchromiumoxosalencomplexes.Effectofaddedphosphoryllig2ands[J].TetraLett,2002,43:2107-2110.[16]CookJB,NicholsonBK,SmithDW.Astructural,spectroscopicandtheoreticalstudyofthetriphenylphosphinechalcogenidecomplexesoftungstencarbonyl,[W(XPPh3)(CO)5],X=O,S,Se[J].JOrgChem,2004,689:860-869.[17]KuntzEG.Hemogeneouscatalysisinwater[J].Chemtech,1987(9):570-574.[18]WeiL,JiangJY,WangYH,etal.HydrogenationofSBScatalyzedbyimmobilizedRu2TPPTScomplexinpolyethermoltensat[J].ChineseChemicalLetters,2005,16(3):338-340.[19]WangY,LaiVW,KwongFY,etal.Synthesisofarylphosphinesviaphosphinationwithtriphenylphosphinebysupportedpalladiumcatalysts[J].Tetrahedron,2004,60:9433-9439.[20]YavariI,AbbasinejadMA,AlizadehA.Anovelapproachtothesynthe2sisofhighlyfunct