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1、++Chem.Rev.1996,96,1737-17551737ElectrophilicNFFluorinatingAgentsG.SankarLal,GuidoP.Pez,*andRobertG.SyvretAirProductsandChemicals,Inc.,7201HamiltonBoulevard,Allentown,Pennsylvania18195-1501ReceivedNovember20,1995(RevisedManuscriptReceivedMay23,1996)Conte
2、ntssuchnucleophilicfluorinatingagentsthatareusefulforlaboratoryuseorfinechemicalsynthesispro-I.Introduction1737cessesarepyridine.HF,Bu4N+HF2-,activatedalkaliII.GeneralPreparativeMethods1738metalfluorides,etc.,andalsoSF4and(diethylamino)-III.SurveyofNFRea
3、gents1741sulfurtrifluoride(DAST),whichcanconvertcarbon-A.NeutralCompoundsR2NF1741oxygentocarbon-fluorinebonds.9,101.SulfonylDerivativesRSO2N(F)R¢1743Thefluorinationofelectron-richcenters,inpar-2.N-FluoroaminesandN-Fluoroamides1743ticular,adirectconversio
4、nofC-HtoC-Flinkages,B.Quaternary(R3N+FA-)Compounds1743isusuallynotfeasiblewithHF-basedchemistry;for1.N-FluoropyridiniumSalts1743thisradicalorelectrophilicsourcesoffluorineare2.SaturatedDerivatives1744needed.Elementalfluorinecanbeusedforthispurpose,butthe
5、rearesignificantremainingchal-C.NitrogenFluorides1744lenges.Atnear-ambienttemperatures,whenactingD.PotentialElectrophilicNFCompounds1744¥asasourceofFradicals,itisquiteindiscriminateIV.ApplicationsinOrganicSynthesis1744initschemistrytowardorganicsubstrate
6、s.However,A.SynthesisofFluoroaromatics1744undercarefullyregulatedconditionsfluorinecanbeB.FluorinationofCarbanions1745ausefulsyntheticreagent.11,12Anefficientperflu-1.SynthesisofR-FluoroCarbonyl1745orinationofhydrocarbonsandsomeetherscan,forCompoundsinst
7、ance,beaccomplishedbytheLaMarandaerosol-2.Synthesisofç-FluoroCarbonyl1747controlledfluorinationtechniques.13AregioselectiveCompoundslimitedintroductionoffluorinebydirectreactionC.FluorinationofOlefins1747withtheelementhasinprinciplebeendemonstratedD.Fluo
8、rinationofOrganometallicCompounds1748formanyorganicsubstrates,includingcarbanions,E.Synthesisof(Fluoromethyl)phosphonatess1748enolates,olefins,andcertainaromatics.ReactionsPrecursorstoMono-andDifluoroolefinsaredonewithN2-d
