|Table of Contents|

RecentProgressinCarbonylativeSuzukiReaction(PDF)

《南京师大学报(自然科学版)》[ISSN:1001-4616/CN:32-1239/N]

Issue:
2015年03期
Page:
1-
Research Field:
特约稿
Publishing date:

Info

Title:
RecentProgressinCarbonylativeSuzukiReaction
Author(s):
HanWeiZhongYanzhenJinFengliDuHongyan
SchoolofChemistryandMaterialsScience,NanjingNormalUniversity,Nanjing210023,China
Keywords:
carbonylativeSuzukireactioncross-couplingreactiontransition-metalcatalysisC1chemistry
PACS:
O621.3
DOI:
-
Abstract:
CarbonylativeSuzukireactionisoneofthemostefficientmethodsforthesynthesisofbiarylketonesandhascausedconsiderableinterest.Inthisreviewthenewestdevelopmentofthetransformationissummarized,andthedevelopmentandapplicationprospectsforthisreactionhavealsobeendiscussed.

References:

[1]IshiyamaT,KizakiH,MiyauraN,etal.Synthesisofunsymmetricalbiarylketonesviapalladium-catalyzedcarbonylativecross-couplingreactionofarylboronicacidswithiodoarenes[J].TetrahedronLett,1993,34(47):7595-7598.
[2]MiyauraN,YamadaK,SuzukiA.Therelativeratesofelectron-richandelectron-deficientalkenecycloadditionstobenzyne.Enhancedelectrophilicityasaconsequenceofalkynebendingdistortions[J].TetrahedronLett,1979,20(36):3437-3440.
[3]LittkeAF,FuGC.AconvenientandgeneralmethodforPd-catalyzedSuzukicross-couplingsofarylchloridesandarylboronicacids[J].AngewChemIntEd,1998,37(24):3387-3388.
[4]OldDW,WolfeJP,BuchwaldSL.Ahighlyactivecatalystforpalladium-catalyzedcross-couplingreactions:room-temperatureSuzukicouplingsandaminationofunactivatedarylchlorides[J].JAmChemSoc,1998,120(37):9722-9723.
[5]LittkeAF,FuGC.Palladium-catalyzedcouplingreactionsofarylchlorides[J].AngewChemIntEd,2002,41(22):4176-4211.
[6]IshiyamaT,KizakiH,HayashiT,etal.Palladium-catalyzedcarbonylativecross-couplingreactionofarylboronicacidswitharylelectrophiles:synthesisofbiarylketones[J].JOrgChem,1998,63(14):4726-4731.
[7]Couve-BonnaireS,CarpentierJF,MortreuxaA,etal.Palladium-catalyzedcarbonylativecross-couplingreactionsofpyridinehalidesandarylboronicacids:aconvenientaccesstoα-pyridylketones[J].TetrahedronLett,2001,42(23):3689-3691.
[8]Couve-BonnaireS,CarpentierJF,MortreuxaA,etal.Palladium-catalyzedcarbonylativecouplingofpyridinehalideswitharylboronicacids[J].Tetrahedron,2003,59(16):2793-2799.
[9]NeumannH,BrennführerA,BellerM.Ageneralsynthesisofdiarylketonesbymeansofathree-componentcross-couplingofarylandheteroarylbromides,carbonmonoxide,andboronicacids[J].ChemEurJ,2008,14(12):3645-3652.
[10]SharifM,Pews-DavtyanA,LukasJ,etal.Palladium-catalyzedcarbonylativetransformationsofbromhexineintobioactivecompoundsasglucocerebrosidaseinhibitors[J].EurJOrgChem,2014(1):222-230.
[11]PredigerP,MoroAV,NogueiraCW,etal.Palladium-catalyzedSuzukicross-couplingof2-haloselenophenes:synthesisof2-arylselenophenes,2,5-diarylselenophenes,and2-arylselenophenylketones[J].JOrgChem,2006,71(10):3786-3792.
[12]Skoda-F?ldesR,Székv?lgyiZ,KollárL,etal.Facilesynthesisofsteroidalphenylketonesviahomogeneouscatalyticcarbonylation[J].Tetrahedron,2000,56(21):3415-3418.
[13]BartaliL,GuarnaA,LariniP,etal.CarbonylativeSuzuki-Miyauracouplingreactionoflactam-,lactone-andthiolactone-derivedenoltriflatesforthesynthesisofunsymmetricaldienones[J].EurJOrgChem,2007(13):2152-2163.
[14]Medio-SimónM,MollarC,RodríguezN,etal.Firstsynthesisofβ-ketosulfoxidesbyapalladium-catalyzedcarbonylativeSuzukireaction[J].OrgLett,2005,7(20):4669-4672.
[15]WuXF,NeumannH,BellerM.Palladium-catalyzedcarbonylativecouplingofbenzylchlorideswitharylboronicacidsinaqueousmedia[J].TetrahedronLett,2010,51(47):6146-6149.
[16]WuXF,NeumannH,BellerM.Palladium-catalyzedcarbonylativeSuzukicouplingofbenzylhalideswithpotassiumaryltrifluoroboratesinaqueousmedia[J].AdvSynthCatal,2011,353(5):788-792.
[17]BjerglundKM,SkrydstrupT,MolanderGA.carbonylativeSuzukicouplingsofarylbromideswithboronicacidderivativesunderbase-freeconditions[J].OrgLett,2014,16(7):1888-1891.
[18]ZhengGM,WangPP,CaiMZ.AnewroutetobiarylketonesviacarbonylativeSuzukicouplingcatalyzedbyMCM-41-supportedbidentatephosphinepalladium(0)complex[J].ChinJChem,2009,27(7):1420-1426.
[19]KantchevEAB,O’BrienCJ,OrganMG.PalladiumcomplexesofN-heterocycliccarbenesascatalystsforcross-couplingreactions—asyntheticchemist’sperspective[J].AngewChemIntEd,2007,46(16):2768-2813.
[20]CovellKJ,McGuinnessDS.Redoxprocessesinvolvinghydrocarbylmetal(N-heterocycliccarbene)complexesandassociatedimidazoliumsalts:ramificationsforcatalysis[J].CoordChemRev,2004,248(7/8):671-681.
[21]HerrmannWA.N-heterocycliccarbenes:anewconceptinorganometalliccatalysis[J].AngewChemIntEd,2002,41(8):1290-1309.
[22]HillierAC,GrasaGA,ViciuMS,etal.Catalyticcross-couplingreactionsmediatedbypalladium/nucleophiliccarbenesystems[J].JOrganometChem,2002,653(1/2):69-82.
[23]NolanSP.ThedevelopmentandcatalyticusesofN-heterocycliccarbenegoldcomplexes[J].AccChemRes,2011,44(2):91-100.
[24]MarionN,NolanSP.Well-definedN-heterocycliccarbenes-palladium(Ⅱ)precatalystsforcross-couplingreactions[J].AccChemRes,2008,41(11):1440-1449.
[25]Díez-GonzálezS,MarionN,NolanSP.N-heterocycliccarbenesinlatetransitionmetalcatalysis[J].ChemRev,2009,109(8):3612-3676.
[26]AndrusMB,MaYD,ZangYF,etal.Palladium-imidazolium-catalyzedcarbonylativecouplingofaryldiazoniumionsandarylboronicacids[J].TetrahedronLett,2002,43(50):9137-9140.
[27]ZhengSZ,XuLW,XiaCG.HighlyefficientN-heterocycliccarbene-palladiumcomplex-catalyzedmulticomponentcarbonylativeSuzukireaction:novelpracticalsynthesisofunsymmetricarylketones[J].ApplOrganometalChem,2007(21):772-776.
[28]O’KeefeBM,SimmonsN,MartinSF.Carbonylativecross-couplingofortho-disubstitutedaryliodides.convenientsynthesisofstericallyhinderedarylketones[J].OrgLett,2008,10(22):5301-5304.
[29]O’KeefeBM,SimmonsN,MartinSF.Facileaccesstostericallyhinderedarylketonesviacarbonylativecross-coupling:applicationtothetotalsynthesisofluteolin[J].Tetrahedron,2001,67(24):4344-4351.
[30]MaertenE,SauthierM,MortreuxA,etal.Palladium-N-heterocycliccarbeneanefficientcatalyticsystemforthecarbonylativecross-couplingofpyridinehalideswithboronicacids[J].Tetrahedron,2007,63(3):682-689.
[31]MaertenE,HassounaF,Couve-BonnaireS,etal.Directsynthesisofbenzoylpyridinesfromchloropyridinesviaapalladium-carbenecatalyzedcarbonylativeSuzukicross-couplingreaction[J].Synlett,2003(12):1874-1876.

[33]QureshiZS,DeshmukhKM,TambadePJ,etal.Asimple,efficient,andrecyclablephosphine-freecatalyticsystemforcarbonylativeSuzukicouplingreactionofarylandheteroaryliodidesrecyclablecatalystforcarbonylativeSuzukicouplingreaction[J].Synthesis,2011(2):243-250.
[33]KhedkarMV,SasakiT,BhanageBM.Efficient,recyclableandphosphine-freecarbonylativeSuzukicouplingreactionusingimmobilizedpalladiumion-containingionicliquid:synthesisofarylketonesandheteroarylketones[J].RSCAdv,2013(3):7?791-7797.
[34]DaiMJ,LiangB,WangCH,etal.AnovelthiourealigandappliedinthePd-catalyzedHeck,SuzukiandSuzukicarbonylativereactions[J].AdvSynthCatal,2004,346(13/14/15):1669-1673.
[35]TambadePJ,PatilYP,PandaAG,etal.Phosphane-freepalladium-catalyzedcarbonylativeSuzukicouplingreactionofarylandheteroaryliodides[J].EurJOrgChem,2009(18):3022-3025.
[36]CaiMZ,PengJ,HaoWY,etal.Aphosphine-freecarbonylativecross-couplingreactionofaryliodideswitharylboronicacidscatalyzedbyimmobilizationofpalladiuminMCM-41[J].GreenChem,2011,13(1):190-196.
[37]JafarpourF,Rashidi-RanjbarP,KashaniAO.Easy-to-executecarbonylativearylationofarylhalidesusingmolybdenumhexacarbonyl:efficientsynthesisofunsymmetricaldiarylketones[J].EurJOrgChem,2011(11):2128-2132.
[38]LiHL,YangM,QiYX,etal.Ligand-freePd-catalyzedcarbonylativecross-couplingreactionsunderatmosphericpressureofcarbonmonoxide:synthesisofarylketonesandheteroaromaticketones[J].EurJOrgChem,2011(14):2662-2667.
[39]ZhouQ,WeiSH,HanW.Insitugenerationofpalladiumnanoparticles:ligand-freepalladiumcatalyzedpivalicacidassistedcarbonylativeSuzukireactionsatambientconditions[J].JOrgChem2014,79(3):1454-1460.
[40]RennerH,SchmucklerG.MetalsandTheirCompoundsintheEnvironment[M].Weinheim:Wiley-VCH,1991.
[41]ZereiniF,AltF.PalladiumEmissionsintheEnvironment[M].BerlinHeidelberg:Springer,2006.
[42]KangSK,YamaguchiT,KimTH,etal.Copper-catalyzedcross-couplingandcarbonylativecross-couplingoforganostannanesandorganoboraneswithhypervalentiodinecompounds[J].JOrgChem,1996,61(26):9082-9083.
[43]ZhongYZ,HanW.Iron-catalyzedcarbonylativeSuzukireactionsunderatmosphericpressureofcarbonmonoxide[J].ChemCommun,2014,50(29):3874-3877.

Memo

Memo:
-
Last Update: 2015-09-30