heck反应的综述

Tetrahedronreportnumber743Non-conventionalmethodologiesfortransition-metalcatalysedcarbon–carboncoupling:acriticaloverview.Part1:TheHeckreactionFranciscoAlonso,a,*IrinaP.Beletskayab,*andMiguelYusa,*aDepartamentodeQuı´micaOrga´nica,FacultaddeCienciasandInstitutodeSı´ntesisOrga´nica(ISO),UniversidaddeAlicante,Apdo.99,E-03080Alicante,SpainbDepartmentofChemistry,LomonosovMoscowStateUniversity,Vorob’evyGory,119992Moscow,RussiaReceived10August2005Availableonline29September2005Contents1.Generalintroduction..........................................................117721.1.Substrates..............................................................117731.2.Catalyticsystems........................................................117731.3.Solvents...............................................................117741.3.1.Supercriticalfluids(SCFs)...........................................117741.3.2.Ionicliquids(ILs)..................................................117741.3.3.Fluorousmedia...................................................117751.3.4.Aqueoussolvents..................................................117751.4.Reactionconditions......................................................117751.4.1.Physicalactivation.................................................117761.4.1.1.Microwave...............................................117761.4.1.2.Ultrasound................................................117761.4.1.3.Highpressure.............................................117761.4.2.Physicochemicalactivation...........................................117760040–4020/$-seefrontmatterq2005ElsevierLtd.Allrightsreserved.doi:10.1016/j.tet.2005.08.054Tetrahedron61(2005)11771–11835Keywords:Heckreaction;Supercriticalfluids;Ionicliquids;Fluorousmedia;Aqueoussolvents;Microwave;Ultrasound;Highpressure;Nanofiltration;Microreactors;Ball-millingconditions.Abbreviations:A,ampere;AAEMA,deprotonatedformof2-(acetoacetoxy)ethylmethacrylate;acac,acetylacetonate;Ad,adamantyl;A336,tricaprylmethylammoniumchloride;atm,atmosphere;bbim,1,3-di-n-butylimidazolium;b,blockcopolymer;bmim,1-butyl-3-methylimidazolium;BINAP,2,20-bis(diphenylphosphino)-1,10-binaphthyl;Boc,tert-butoxycarbonyl;BTF,benzotrifluoride(a,a,a-trifluorotoluene);Cbz,benzyloxycarbonyl;co,copolymer;COD,1,5-cyclooctadiene;Cy,cyclohexyl;DAB,1,4-diaminobutane;dba,dibenzylideneacetone;DBU,1,8-diazabicyclo[5.4.0]undec-7-ene;DEA,N,N-diethylacetamide;DEC,dendrimer-encapsulatedcatalyst;dendr,dendrimer;DIPEA,diisopropylethylamine;DMA,N,N-dimethylacetamide;DMF,dimethylformamide;DMG,N,N-dimethylglycine;dppp,1,3-diphenylphosphinopropane;EDG,electron-donatinggroup;EWG,electron-withdrawinggroup;Fc,ferrocenyl;F-dppp,fluorous-tagged1,3-bis(diphenylphosphino)propane;HDAPS,N-hexadecyl-N,N-dimethyl-3-ammonio-2-propanesulfonate;Hex,hexyl;IL,ionicliquid;LDH,layereddoublehydroxide;M,metal;MCM-41,hexagonallypackedmesoporousmolecularsieves;MW,microwave;Nf,nonaflate(nonafluoro-n-butane-1-sulfonyl);NMP,N-methylpyrrolidinone;Pc,criticalpressure;PAMAM,poly(amidoamine);PEG,poly(ethyleneglycol);pmim,1-n-pentyl-3-methylimidazolium;PNIPAM,poly(N-isopropylacrylamide);PNP,p-nitrophenyl;PS,polystyrene;Py,pyridyl;RCM,ring-closingmetathesis;ROMP,ring-openingmetathesispolymerisation;rt,roomtemperature;SAPO,silicoaluminophosphate;sc,supercritical;SCF,supercriticalfluid;SCM,shellcross-linkedmicelles;SDS,sodiumdodecylsulfate;TBAA,tetra-n-butylammoniumacetate;TBAB,tetra-n-butylammoniumbromide;TBAC,tetra-n-butylammoniumchloride;TBAF,tetra-n-butylammoniumfluoride;TEAC,tetraethylammoniumchloride;Tf,trifluoromethanesulfonyl;TPPDS,bis(p-sulfonatophenyl)phenylphosphanedipotassiumsalt;Na-TPPMS,mono(m-sulfonatophenyl)diphenylphosphanemonosodiumsalt;m-TPPTC,tris(m-carboxyphenyl)phosphanetrilithiumsalt;TPPTS,tris(m-sulfonatophenyl)phosphanetrisodiumsalt;TXPTS,tris(4,6-dimethyl-3-sulfonatophenyl)phosphanetrisodiumsalt;Tc,criticaltemperature;THF,tetrahydrofuran;THP,tetrahydropyranyl;TFA,trifluoroaceticacid;Tol,tolyl;TOF,turnoverfrequency(molofproductpermolofcatalysthK1);TON,turnovernumber(molofproductpermolofcatalyst);Ts,p-toluenesulfonyl;ttmpp,tris-(2,4,5-trimethoxyphenyl)phosphane;wt,weight;XAFS,X-rayabsorptionfinestructure.*Correspondingauthors.Tel./fax:C34965903549;(F.A.;M.Y.);fax:C7959381844;(I.P.B.);e-mailaddresses:[e-mail];[e-mail];[e-mail]..........................................117761.4.2.2.Microemulsions............................................117771.4.3.Electrochemicalactivation...........................................117771.5.Miscellaneousnon-conventionaltechniques.....................................117771.5.1.Nanofiltration.....................................................117771.5.2.Microreactors.....................................................117771.5.3.Ball-millingconditions..............................................117782.Objectivesandorganisation.....................................................117783.IntroductiontotheHeckreaction..........................................