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XChen,X-YThenextsignificantimprovementtowardsustainableSonogashira-Hagiharacouplingswasachievedduringacollaborationbetweenoneofthe authorsFromtheseriesofpalladium-assistedC–Cbondformation,theSonogashiracouplingreactionhasbeenidenti-fiedasaviablesyntheticmethodforthe preparationofvariousThecouplingofarylorvinylhalideswithterminalacetylenescatalysedbypalladiumandothertransitionmetals,commonlytermedas Sonogashiracross-couplingreaction,is1, Inthisstudy,wedemonstratedthatnp-PdcatalyzestheSonogashiracouplingreactionintheabsenceofcuprousions, phosphineligands,oramineadditivesSonogashiracross-couplingreaction)topalladiumcomplexThisreactionisexothermic(∆H=–kcal/mol,∆G=kcal/mol), andtheBr–PddistanceintheresultingTheSonogashirareactionisacross-couplingreactionofavinylorarylhalidewithaterminalalkynetoformaC–CbondIn itsoriginalform,theSonogashirareactionisSonogashiracouplingSonogashiracoupling3isversatileandhasbeenappliedtoprepareseveralterminalandinternal acetylenes.ItemploysapalladiumcatalystaswellP.Lei,Y.Wang,C.Zhang,X.Hu,J.Feng,Z.Ma,X.Liu,R.Szostak,M.Szostak,Org.Lett.,,,AConvenient, Efficient,andInexpensiveCopper(I)ComplexCatalyzedSonogashiraCross-Couplingofo-IodoanilineswithTerminalAlkynes.Asurveyoftheliteraturereveals thatcopperacetylideundergoeshomocouplingwhenexposedtoair,andthefirstobservationtothiseffectwasmadebyGlaser5a,basearlyasSonogashiracrosscouplingreactionsfreeofCuand/orphos-phinehasthereforedrawnhugeattentioninthelastadeTheSonogashirareactionisacross-couplingreactionusedin organicsynthesistoformcarbon–carbonbondsJournalofChemicalResearch,Vol()–TheAuthor(s)Articlereuseguidelines:DOI:/Zhou,Synthesis,,,The Sonogashirareaction(alsocalledtheSonogashira-Hagiharareaction)isthecrosscouplingofarylorvinylhalideswithterminalalkynestogenerateconjugated enynesandarylalkynes(Scheme1)Thereactiontypicallyproceedsinthepresenceofapalladium(0)catalyst,acopper(I)cocatalyst,andaniminebaseAlternative proceduresInthispaper,wepresentamethodtodiminishacetylenebicouplingandenhancethedesiredcross-coupling.Thereactionconditionsaremild,and manyreactionscanbecross-couplingsSonogashira–Hagiharacross-couplingofaterminalalkynewithanarylhalideinthepresenceofCuandcatalyzedbyCd providesaneasymethodforthesynthesisofavarietyofSonogashiracouplingisoneofthecornerstonePalladiummediatedcrosscouplingreactions,givinga directandhighyieldaccesstosymmetricandnon-symmetricalkyneswithhightoleranceofsubstitThecouplingofarylorvinylhalideswithterminalacetylenes catalysedbypalladiumandothertransitionmetals,commonlytermedasSonogashiracross-couplingreaction,isoneofthemostThecouplingofarylorvinyl halideswithterminalacetylenescatalysedbypalladiumandothertransitionmetals,commonlytermedasSonogashiracross-couplingreaction,isoneofthemost importantandwidelyusedsp–spcarbon–carbonbondformationreactionsinorganicsynthesis,frequentlyemployedinthesynthesisofnaturalproducts,b Sonogashiracouplingreactions:Synthesisofsubstitutedmethyl(methylthio)pyrimidinescatalyzedbyPd–Cu.