cinnamonitriles_cinnamonitrile(7)

Thecross-couplingreactionofalkenylandarylhalideswithorganoboranederivativesinthepres-enceofapalladiumcatalystandabase,knownas

ChemicalReviews,2005,Vol.105,No.83137

the“Suzukireaction”,hasoftenbeencarriedoutinanorganic/aqueousmixedsolvent(eq178).675The

reactionwasinitiallycarriedoutinamixtureofbenzeneandaqueousNa2CO3。676However,thereac-tionproceedsmorerapidlyinahomogeneousmedium(e。g。,aqueousDME)。Thisconditionworkssatisfac-torilyinmostaryl-arylcouplings。677Thus,dienesareconvenientlypreparedfromthecorrespondingalk-enylboraneandvinylbromideinrefluxingTHFinthepresenceofPd(PPh3)4andanaqueousNaOHsolution。678TheuseofaqueousTlOHinsteadofNaOHorKOHsignificantlyincreasedtherateofthecoupling。InKishi’spalytoxinsynthesis,thecross-couplingbetweenthealkenylboronicacidandtheiodoalkenewasaccomplishedstereoselectivelyatroomtemperature。

679TheTlOHpromotedcouplinghasalsobeenusedeffectivelyinRoush’ssynthesisofkijanimicin,680Nicolaou’ssynthesisof(12R)-hy-droxyeicosatetraenoicacid(HETE),681andEvans’synthesisofrutamycinB。682Multigram-scalesyn-thesisofabiphenylcarboxylicacidderivativeusedaPd/C-mediatedSuzuki-couplingapproach。cinnamonitriles683TheSuzukireactioninanaqueousmediumhasalsobeenusedinotherapplicationssuchasthesynthesisofmonosubstitutedarylferrocenes,684insulatedmolec-ularwires(conjugatedpolyrotaxanes),685cyclodextrin[2]rotaxanes,686unprotectedhalonucleosides,6876-sub-stitutedN-Boc3,4-dihydro-2H-pyridines,688heteroaryl-benzoicacids,689alkenylpurines,6906-alkyl-N-alk-oxycarbonyl-3,4-dihydro-2H-pyridines,691coumarinicderivatives,692andbiarylcolchicinoids。693Thereac-tionhasbeenusedinsynthesizingacombinatoriallibraryofbiaryls。694

本文来自电脑杂谈，转载请注明本文网址：
http://www.pc-fly.com/a/shumachanpin/article-39383-7.html