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Practical Synthetic Organic Che…

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简介:本文档为《Practical Synthetic Organic Chemistry_Reactions, Principles and Techniquespdf》,可适用于学术研究领域,主题内容包含PRACTICALSYNTHETICORGANICCHEMISTRYPRACTICALSYNTHETICORGANICCHEMISTRYReacti符等。

PRACTICALSYNTHETICORGANICCHEMISTRYPRACTICALSYNTHETICORGANICCHEMISTRYReactions,Principles,andTechniquesEditedbySTEPHANECARONCopyrightbyJohnWileySons,IncAllrightsreservedPublishedbyJohnWileySons,Inc,Hoboken,NewJerseyPublishedsimultaneouslyinCanadaNopartofthispublicationmaybereproduced,storedinaretrievalsystem,ortransmittedinanyformorbyanymeans,electronic,mechanical,photocopying,recording,scanning,orotherwise,exceptaspermittedunderSectionsoroftheUnitedStatesCopyrightAct,withouteitherthepriorwrittenpermissionofthePublisher,orauthorizationthroughpaymentoftheappropriatepercopyfeetotheCopyrightClearanceCenter,Inc,RosewoodDrive,Danvers,MA,(),fax(),oronthewebatwwwcopyrightcomRequeststothePublisherforpermissionshouldbeaddressedtothePermissionsDepartment,JohnWileySons,Inc,RiverStreet,Hoboken,NJ,(),fax(),oronlineathttp:wwwwileycomgopermissionLimitofLiabilityDisclaimerofWarranty:Whilethepublisherandauthorhaveusedtheirbesteffortsinpreparingthisbook,theymakenorepresentationsorwarrantieswithrespecttotheaccuracyorcompletenessofthecontentsofthisbookandspecificallydisclaimanyimpliedwarrantiesofmerchantabilityorfitnessforaparticularpurposeNowarrantymaybecreatedorextendedbysalesrepresentativesorwrittensalesmaterialsTheadviceandstrategiescontainedhereinmaynotbesuitableforyoursituationYoushouldconsultwithaprofessionalwhereappropriateNeitherthepublishernorauthorshallbeliableforanylossofprofitoranyothercommercialdamages,includingbutnotlimitedtospecial,incidental,consequential,orotherdamagesForgeneralinformationonourotherproductsandservicesorfortechnicalsupport,pleasecontactourCustomerCareDepartmentwithintheUnitedStatesat(),outsidetheUnitedStatesat()orfax()WileyalsopublishesitsbooksinavarietyofelectronicformatsSomecontentthatappearsinprintmaynotbeavailableinelectronicformatsFormoreinformationaboutWileyproducts,visitourwebsiteatwwwwileycomLibraryofCongressCataloginginPublicationData:Practicalsyntheticorganicchemistry:reactions,principles,andtechniqueseditedbyStephaneCaronpcmIncludesindexISBN(pbk)Organiccompounds–SynthesisICaron,StephaneQDP’–dcPrintedintheUnitedStatesofAmericaoBooKISBN:ePDFISBN:ePubISBN:CONTENTSForewordviiPrefaceixContributorsxiAliphaticNucleophilicSubstitutionJadeDNelsonAdditiontoCarbon–HeteroatomMultipleBondsRajappaVaidyanathanandCarrieBrockwayWagerAdditiontoCarbon–CarbonMultipleBondsJohnARaganNucleophilicAromaticSubstitutionStephaneCaronandArunGhoshElectrophilicAromaticSubstitutionStephaneCaronSelectedMetalMediatedCrossCouplingReactionsStephaneCaron,ArunGhosh,SallyGutRuggeri,NathanDIde,JadeDNelson,andJohnARaganRearrangementsDavidHBRipinEliminationsSallyGutRuggerivReductionsSallyGutRuggeri,StephaneCaron,PascalDube,NathanDIde,KristinEPrice,JohnARagan,andShuYuOxidationsDavidHBrownRipinSelectedFreeRadicalReactionsNathanDIdeSynthesisof“Nucleophilic”OrganometallicReagentsDavidHBrownRipinSynthesisofCommonAromaticHeterocyclesStephaneCaronAccesstoChiralityRobertWDuggerSyntheticRouteDevelopmentofSelectedContemporaryPharmaceuticalDrugsStephaneCaronGreenChemistryJuanCColbergNamingCarbocyclesandHeterocyclesHeatherNFrostandDavidHBrownRipinpKaDavidHBrownRipinGeneralSolventPropertiesStephaneCaronPracticalChemistryConcepts:TipsforthePracticingChemistorThingsTheyDon’tTeachYouinSchoolSallyGutRuggeriFunctionalGroupInterconversionIndexIndexviCONTENTSFOREWORDWhileallpractitionersintheartrecognizethatsyntheticorganicchemistryservessociety,itisnotalwaysappreciatedtheotherwayaroundnamelythatsocietydoesnotassociatethephenomenalrewardsthatarederivedfromourabilitytoassemblecomplexfunctionalmoleculesIndeed,theachievementsofthepharmaceuticalindustryareunderpinnedbymoleculardesignandsynthesisofvirtuallyallthehealingdrugsubstancesthatarecurrentlyonthemarket,whichbenefitmankindandcurehumandiseasesThereis,inmyview,nothingnoblerthanthisworthwhiletaskHowever,synthesisofthecomplexfunctionalarchitecturesisnotatrivialorroutineprocessThisisalwaysmademoredifficultonscalingupofthechemistriestocomplywithcurrentstandardsofsafety,robustness,costs,quality,andenvironmentalimpactI,therefore,verymuchwelcomethisnewtextbook,PracticalSyntheticOrganicChemistry:Reactions,Principles,andTechniques,whichgivesusaninspiringandpragmaticglimpseatthemostcommonlyusedandeffectivesynthesisproceduresonscaleThisuniquetextbookhasbeenwrittenbyexpertsinthefieldandprovidesaninsightandcritiqueofthekeyeffectivemethodsformolecularassemblyItwillbeagreatstartingpointforanyonedevelopingtheircareerinthisworthyindustryTheorganizationandchaptertitlesreflectarefreshingapproachtoexplainingacomplicatedsciencecoveringallthemajorbondconstructionmethodsandfunctionalcontrolelementsnecessaryformodernsyntheticplanningandexecutionTheauthorshaveincorporatedchaptersonimportanttopicssuchastheeffectivenessofrearrangementprocesses,radicalreactions,accesstochirality,andgreenchemistry,whicharenotcapturedasagroupinmoretraditionaltextsFurthermore,theeducationalcomponentofthisbookhighlightingnomenclature,pKaknowledge,solventproperties,andtipsofthetradefromthepracticingchemistagainaddsvalueinprovidingafeastofinformationthatotherwiseisdispersedovermanysourcesorissimplylockedupinthepersonaldatabaseofknowledgeofthoseexperiencedintheartviiThecreativespiritofthisareaofscienceinbringingnewfunctionalmoleculesinourworldforthefirsttimeforthebettermentofusallisenduringandwillcontinuetoseednewdiscoveriesformanyyearstocomeSTEVENVLEYCambridge,UKviiiFOREWORDPREFACEDespitetherelativematurityofthefieldoforganicchemistry,moleculescontinuetopresentsyntheticchemistswithsignificantchallenges,especiallyastheexpectationsforsynthetic,material,andenergyefficiencycontinuetointensifyInresponsetothesechallenges,organicchemistshavecontinuedtodevelopinnovativenewsyntheticmethodsManyoftheserecentlydevelopedsyntheticmethodsallowforachievementofevermoreimpressivechemo,enantio,diastereo,andregioselectivityAdditionally,newsyntheticmethodsareprovidingchemistswithnovelreactionsandenablingsyntheticstrategiesthatwouldhavepreviouslybeenimpracticalorimpossibleWhilewearefascinatedbythemultitudeofpowerfulsyntheticmethodsthathavebeendevelopedinrecentyears,thesemethodswerenotthedirectinspirationforthisbookInstead,theimpetusforthisbookwasactuallyanarticlerequestforaspecialissueofChemicalReviewsonprocesschemistry(Vol,No,July)AgroupofPfizerprocesschemists,attheGroton(CT)site,electedtowriteareviewofoxidationsperformedonlargescaleThisreviewwasdividedamongseveralauthorsandservedasthebasisforChapterinthisbookMypersonalcontributiontothereviewarticlewasthesectioncoveringC–Ooxidations,andIwassurprisedbywhatIlearneduponfurtherinvestigationofthisseeminglymundanetopicWhileanumberofeffectivemethodsexistfortheconversionofprimaryalcoholstoaldehydes,onlytwogeneralmethodshavebeenusedconsistentlyandsuccessfullyonmanufacturingscale:MoffatttypeandTEMPOmediatedoxidationsUponcompletionofthisreview,IaskedmyselfifthiswouldbetrueforotherchemicaltransformationsBeyondsimplecuriosity,thisquestionisrelevantbecausesearchengineslikeSciFinderandReaxyscanrapidlysearchthroughthechemicalliteratureandidentifylargenumbersofpotentiallyrelevantreactionsreferencesForexample,asimplesearchforthenitrationofanareneresultsinthousandsofexamplesofthistransformationHowdoesonesortthroughthisincrediblewealthofinformationCaron,SDugger,RWRuggeri,SGRagan,JARipin,DHBChemRev,,ixInthisageofinformationoverload,wethoughtthatasimplecollectionofprovenmethodologiesmightbeofvaluetopracticingsyntheticchemistsWhilemanytextbooksofferacompendiumofthemanysyntheticmethodsthatareavailable,wesetouttocreateaguidethatwouldhelpselectthefirstfewconditionstoattemptforagiventransformationThismightbeofparticularvaluewhenthesubstrateofinterestisdifficulttoaccessinsufficientquantitiesforalargescreenofreactionconditionsTheauthorsagreedthattheobjectivewouldnotnecessarilybetofindtheoriginalreportortheverybestprocedureforagivenreaction,butrathertoidentifyreactionconditionsthatworkreliablywelloverthebroadestpossiblerangeofsubstratesItwasaprerequisiteforthereferencescitedinthistextbookthatexperimentaldatawasprovided,preferablyonamultigramscale,andpreferablyusingreactionconditionsthatwouldbeamenabletoscaleupIntherarecaseswheresuchexperimentaldatawasnotidentified,theauthorsusedtheirdiscretiontoselectreactionconditionsthatwewouldexpecttoscaleupreasonablywellNotsurprisingly,manyoftheexamplescitedinthistextbookcomefromOrganicSynthesesorfromjournalslikeOrganicProcessResearchandDevelopmentandTheJournalofOrganicChemistryWealsoagreedthatpatentliteraturewouldbeavoided,ifpossible,sinceitisnotalwayseasilyaccessedandorinterpretedFinally,wemadeanefforttofocusonreferencespublishedafterInadditiontothecompilationofreliablemethodsforaccomplishingvariouschemicaltransformations,wehavetriedtoprovidethereaderwithsomeinformationthatmaynotbecommonknowledgeoutsideofprocesschemistrygroupsThesecondportionofthisbookfocusesonthistypeofinformationHowcanchiralbuildingblocksbeaccessedmostefficientlyWhatarethemostreliablemethodsforpreparingandnamingcommonheterocyclesWhyaresomesolventsfavoredoverothersHowdoesthesynthesisofadrugevolvethroughoutdevelopmentWhatdoesitmeantohaveagreensynthesisWehopethatreaderswillfindsomeusefulandpracticalinformationinthissectionofthebookThecompletionofthisendeavorwouldhaveneverbeenpossiblewithoutthecommitmentofseveralofmycolleaguesatPfizerwhoagreedtothepreparationandcollectivereviewofthechaptersWearealsoextremelygratefultoourmanagementforsupportingtheprojectIwouldspecificallyliketothankJodiGaynor,LisaLentini,andKimWhitefortheiradministrativesupportIwouldalsoliketothankKrisNJonesforherassistanceineditingthebookThecommitmentandsupportofourcollaboratorsatWileyInterscienceareverymuchappreciatedWeespeciallyappreciatedtheirpatienceasourdeadlinecameandpassedBuildingeachchapterofthismanuscriptservedasanexcellentchemistryrefreshercoursefortheauthors,andwelearnedalotofnewchemistryintheprocessWesincerelyhopeyouenjoythesameexperienceasyoureadthisbookxPREFACECONTRIBUTORSStephaneCaron,SeniorDirector,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,GrotonCT,,stephanecaronpfizercomJuanColberg,APIandAnalyticsTechnologyLeader,TechnologyStrategicSourcing,PfizerWorldwideRD,EasternPointRoad,MSD,GrotonCT,,JuancolbergpfizercomPascalDube,PrincipalScientist,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,GrotonCT,,pascaldubepfizercomRobertWDugger,ResearchFellow,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,GrotonCT,,robertwduggerpfizercomHeatherNFrost,ChemistrySourcingLead,ExternalResearchSolutionsCenterofEmphasis,PfizerWorldwideRD,EasternPointRd,MS,Groton,CT,heathernfrostpfizercomArunGhosh,ArchChemicals,ProcessTechnologiesGroup,KnotterDrive,CheshireCT,,arunghoshsbcglobalnetNathanDIde,PrincipalScientist,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,GrotonCT,,nathandidepfizercomJadeDNelson,AssociateResearchFellow,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,Groton,CT,jadenelsonpfizercomKristinEPrice,SeniorScientist,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MS,Groton,CT,kristinepricepfizercomJohnARagan,AssociateResearchFellow,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,Groton,CT,johnaraganpfizercomxiDavidHBrownRipin,ScientificDirector,DrugAccessTeam,ClintonHealthAccessInitiative,Boston,MA,dripinclintonHealthAccessorgSallyGutRuggeri,AssociateResearchFellow,ResearchAPI,PfizerWorldwideRD,EasternPointRoad,MS,Groton,CT,sallygutpfizercomRajappaVaidyanathan,AssociateResearchFellow,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,Groton,CT,rajappavaidyanathanpfizercomCarrieBWager,SeniorPrincipalScientist,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,Groton,CT,carriebwagerpfizercomShuYu,AssociateResearchFellow,ChemicalRD,PfizerWorldwideRD,EasternPointRoad,MSD,Groton,CT,shuyupfizercomxiiCONTRIBUTORSALIPHATICNUCLEOPHILICSUBSTITUTIONJadeDNelsonINTRODUCTIONNucleophilicsubstitutionreactionsatanaliphaticcenterareamongthemostfundamentaltransformationsinclassicalsyntheticorganicchemistry,andprovidethepracticingchemistwithproventoolsforsimplefunctionalgroupinterconversionaswellascomplextargetorientedsynthesisConventionalSNdisplacementreactionsinvolvingsimplenucleophilesandelectrophilesarewellstudiedtransformations,areamongthefirstconceptslearnedbychemistrystudentsandprovidealaunchingpadformorecomplexsubjectmattersuchasstereochemistryandphysicalorganicchemistryAhighlevelsurveyofthechemicalliteratureprovidesanoverwhelmingmassofinformationregardingaliphaticnucleophilicsubstitutionreactionsThischapterattemptstohighlightthosemethodsthatstandoutfromtheothersintermsofscope,practicality,andscalabilityOXYGENNUCLEOPHILESReactionswithWaterHydrolysisofAlkylHalidesThereactionofwaterwithanalkylhalidetoformthecorrespondingalcoholisrarelyutilizedintargetorientedorganicsynthesisInstead,conversionofalcoholstotheircorrespondinghalidesismorecommonsincemethodsforthesynthesisofhalidesarelessabundantNonetheless,alkylhalidehydrolysiscanprovidesimple,efficientaccesstoprimaryalcoholsundercertaincircumstancesNamely,thehydrolysisofactivatedbenzylicorallylichalidesisafacilereaction,andfollowingbenzylicorallylichalogenation,providesasimpleapproachtothesynthesisofthisPracticalSyntheticOrganicChemistry:Reactions,Principles,andTechniques,FirstEditionEditedbyStephaneCaronJohnWileySons,IncPublishedbyJohnWileySons,IncsubsetofalcoholsTypicalconditionsinvolvetreatmentofthealkylhalidewithamildbaseinanacetonewateroracetonitrilewatermixedsolventsystemModerateheatingwillacceleratethereaction,andiscommonlyemployedONCOHBrONCOHHONaCO:acetoneHOC,hHydrolysisofgemDihalidesGeminaldihalidescanbeconvertedtoaldehydesorketonesviadirecthydrolysisThedesiredconversioncanbemarkedlyacceleratedbyheatinginthepresenceofanacidorabase,orbyincludinganucleophilicaminepromotersuchasdimethylamineOMeMeOBrBrOMeMeOOHaqHNMeC,–hIntheexamplebelowfromSnapperandcoworkers,atrichlorointermediatewaspreparedfrompmethoxystyreneviatheKharaschadditionof,,trichloroethaneContactwithsilicageleffectedeliminationofthebenzylicchlorideaswellashydrolysisofthegeminaldichloridemoietytoyieldthea,bunsaturatedmethylketoneingoodoverallyieldMeOMeOMeClClClMeOMeOSiORuPhPCyPCyClClClCCHC,hHydrolysisof,,Trihalides,,TrihalidesareattheappropriateoxidationstatetoserveascarboxylicacidprecursorsThesecompoundsreactreadilywithwateratacidicpH,providingthecorrespondingacidsinhighyield,andoftenatambienttemperatureTrichloromethylgroups,ratherthantribromoortriiodoanalogs,aremoreoftenutilizedduetosuperioraccessvianucleophilicdisplacementreactionsbytrichloromethylanionsLee,HBZaccaro,MCPattarawarapan,MRoy,SSaragovi,HUBurgess,KJOrgChem,,–Bankston,DSynthesis,–Lee,BTSchrader,TOMartinMatute,BKauffman,CRZhang,PSnapper,MLTetrahedron,,–Martins,MAPPereira,CMPZimmermann,NEKMoura,SSinhorin,APCunico,WZanatta,NBonacorso,HGFlores,ACFSynthesis,–ALIPHATICNUCLEOPHILICSUBSTITUTIONNNEtOCClNNEtOCOHHCl,hHHThetrifluoromethylgrouphasseenincreasedapplicationinthepharmaceuticalindustryinrecentyearsduetoitsrelativemetabolicstabilityAlthoughtrifluoromethylgroupsaresusceptibletovigoroushydrolyticconditions,theyarenotfrequentlyutilizedascarboxylicacidprecursorsduetotherelativeexpenseofincorporatingfluorineintobuildingblocksHowever,anincreasinglycommonsyntheticapplicationoftheCFfunctionishighlightedbytheexamplebelowAlkalinehydrolysisofatrifluoromethylketoneprovidesthecorrespondingcarboxylicacidingoodyieldHere,theCFgroupisnotthepointofnucleophilicattackbywaterInstead,thestronginductiveeffectofthethreehighlyelectronegativefluorineatomsmakesthetrifluoromethylanionanexcellentleavinggroup,andattackoccursatthecarbonylcarbonOOCFOOOHKOH,HO,EtOHrt,hOEtHydrolysisofAlkylEstersofInorganicAcidsAlkalinehydrolysisofinorganicestersmayproceedthroughcompetingmechanisms,asillustratedbythemesylateandboricacidmonoesterinthefollowingschemeSulfonatehydrolysisfavorstheproductofstereochemicalinversion,viadirectSNattackatthecarbonbearingthesulfonateIncontrast,thecorrespondingboronderivativeishydrolyzedunderid

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