Thedevelopmentofmethodsforthedirectconversionofcarbonshydrogenbondsintocarbon-oxygen,carbon-halogen,carbon-nitrogen,carbon-sulfur,andcarbon-carbonbondsremainsacriticalchallengeinorganicchemistry.Mildandselectivetransformationsofthistypewillundoubtedlyfindwidespreadapplicationacrossthechemicalfield,includinginthesynthesisofpharmaceuticals,naturalproducts,agrochemi-cals,polymers,andfeedstockcommoditychemicals.Traditionalapproachesfortheformationofsuchfunctionalgroupsrelyon prefunctionalizedstartingmaterialsforbothreactivityandselectivity.However,therequirementforinstallingafunctionalgrouppriortothedesiredC-O,CsX,C-N,C-S,orC-Cbondaddscostlychemicalstepstotheoverallconstructionofamolecule.Assuch,circumventingthisissuewillnotonlyimproveatomeconomybutalsoincreasetheoverallefficiencyofmultistepsyntheticsequences. DirectC-Hbondfunctionalizationreactionsarelimitedbytwofundamentalchallenges:(i)theinertnatureofmostcarbon-hydrogenbondsand(ii)therequirementtocontrolsiteselectivityinmoleculesthatcontaindiverseC-Hgroups.AmultitudeofstudieshaveaddressedthefirstchallengebydemonstratingthattransitionmetalscanreactwithC-HbondstoproduceCsMbondsinaprocessknownas“C-Hactivation”.1TheresultingCsMbondsarefarmorereactivethantheirC-Hcounterparts,andinmanycasestheycanbeconvertedtonewfunctionalgroupsundermildconditions. Thesecondmajorchallengeisachievingselectivefunctional-izationofasingleC-Hbondwithinacomplexmolecule.Whileseveraldifferentstrategieshavebeenemployedtoaddressthisissue,themostcommon(andthesubjectofthecurrentreview)involvestheuseofsubstratesthatcontaincoordinatingligands.Theseligands(oftentermed“directinggroups”)bindtothemetalcenterandselectivelydeliverthecatalysttoaproximalC-Hbond.Manydifferenttransitionmetals,includingRu,Rh,Pt,andPd,undergostoichiometricligand-directedC-Hactivationreactions(alsoknownascyclometalation).2,3Furthermore,overthepast15years,avarietyofcatalyticcarbon-carbonbond-formingprocesseshavebeendevelopedthatinvolvecyclometalationasakeystep.1b-d,4Thecurrentreviewwillfocusspecificallyonligand-directedC-Hfunctionalizationreactionscatalyzedbypalladium.Palladiumcomplexesareparticularlyattractivecatalystsforsuchtransforma-tionsforseveralreasons.First,ligand-directedC-Hfunctional-izationatPdcenterscanbeusedtoinstallmanydifferenttypesofbonds,includingcarbon-oxygen,carbon-halogen,carbon-nitrogen,carbon-sulfur,andcarbon-carbonlinkages.Fewothercatalystsallowsuchdiversebondconstructions,5-7andthisversatilityispredominantlytheresultoftwokeyfeatures:(i)thecompatibilityofmanyPdIIcatalystswithoxidants,and(ii)theabilitytoselectivelyfunctionalizecyclopalladatedintermediates.Second,palladiumparticipatesincyclometalationwithawidevarietyofdirectinggroupsand,unlikemanyothertransitionmetals,readilypromotesC-Hactivationatbothsp2andsp3C-Hsites.Finally,thevastmajorityofPd-catalyzeddirectedC-Hfunction-alizationreactionscanbeperformedinthepresenceofambientairandmoisture,makingthemexceptionallypracticalforapplica-tionsinorganicsynthesis
Thedevelopmentofmethodsforthedirectconversionofcarbonshydrogenbondsintocarbon-oxygen,carbon-halogen,carbon-nitrogen,carbon-sulfur,andcarbon-carbonbondsremainsacriticalchallengeinorganicchemistry.Mildandselectivetransformationsofthistypewillundoubtedlyfindwidespreadapplicationacrossthechemicalfield,includinginthesynthesisofpharmaceuticals,naturalproducts,agrochemi-cals,polymers,andfeedstockcommoditychemicalsTraditionalapproachesfortheformationofsuchfunctionalgroupsrelyon prefunctionalizedstartingmaterialsforbothreactivityandselectivityอย่างไรก็ตาม โอ therequirementforinstallingafunctionalgrouppriortothedesiredC, CsX, C-N, C-S, orC-Cbondaddscostlychemicalstepstotheoverallconstructionofamolecule.Assuchcircumventingthisissuewillnotonlyimproveatomeconomybutalsoincreasetheoverallefficiencyofmultistepsyntheticsequences DirectC-Hbondfunctionalizationreactionsarelimitedbytwofundamentalchallenges: (i) theinertnatureofmostcarbon-hydrogenbondsand (ii) therequirementtocontrolsiteselectivityinmoleculesthatcontaindiverseC-HgroupsAmultitudeofstudieshaveaddressedthefirstchallengebydemonstratingthattransitionmetalscanreactwithC-HbondstoproduceCsMbondsinaprocessknownas "C-Hactivation" .1TheresultingCsMbondsarefarmorereactivethantheirC-Hcounterparts, andinmanycasestheycanbeconvertedtonewfunctionalgroupsundermildconditions Thesecondmajorchallengeisachievingselectivefunctional-izationofasingleC-HbondwithinacomplexmoleculeWhileseveraldifferentstrategieshavebeenemployedtoaddressthisissue, involvestheuseofsubstratesthatcontaincoordinatingligands themostcommon (andthesubjectofthecurrentreview)BindtothemetalcenterandselectivelydeliverthecatalysttoaproximalC-Hbond.Manydifferenttransitionmetals,includingRu,Rh,Pt,andPd Theseligands (oftentermed "directinggroups")undergostoichiometricligand-directedC-Hactivationreactions (alsoknownascyclometalation) 2, 3Furthermore, overthepast15years, avarietyofcatalyticcarbon-carbonbond-formingprocesseshavebeendevelopedthatinvolvecyclometalationasakeystep.1b-d, 4Thecurrentreviewwillfocusspecificallyonligand-directedC-HfunctionalizationreactionscatalyzedbypalladiumPalladiumcomplexesareparticularlyattractivecatalystsforsuchtransforma-tionsforseveralreasons.First,ligand-directedC-Hfunctional-izationatPdcenterscanbeusedtoinstallmanydifferenttypesofbonds,includingcarbon-oxygen,carbon-halogen,carbon-nitrogen,carbon-sulfur,andcarbon-carbonlinkages.Fewothercatalystsallowsuchdiversebondconstructions, 5-7andthisversatilityispredominantlytheresultoftwokeyfeatures:(thecompatibilityofmanyPdIIcatalystswithoxidants i) และ (ii) theabilitytoselectivelyfunctionalizecyclopalladatedintermediatesสอง palladiumparticipatesincyclometalationwithawidevarietyofdirectinggroupsand, unlikemanyothertransitionmetals, readilypromotesC-Hactivationatbothsp2andsp3C-Hsites.FinallythevastmajorityofPd-catalyzeddirectedC-Hfunction-alizationreactionscanbeperformedinthepresenceofambientairandmoisture, makingthemexceptionallypracticalforapplica-tionsinorganicsynthesis
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Thedevelopmentofmethodsforthedirectconversionofcarbonshydrogenbondsintocarbon-oxygen,carbon-halogen,carbon-nitrogen,carbon-sulfur,andcarbon-carbonbondsremainsacriticalchallengeinorganicchemistry.Mildandselectivetransformationsofthistypewillundoubtedlyfindwidespreadapplicationacrossthechemicalfield,includinginthesynthesisofpharmaceuticals,naturalproducts,agrochemi-cals,polymers,andfeedstockcommoditychemicals.Traditionalapproachesfortheformationofsuchfunctionalgroupsrelyon prefunctionalizedstartingmaterialsforbothreactivityandselectivity.However,therequirementforinstallingafunctionalgrouppriortothedesiredC-O,CsX,CN,CS,orC-Cbondaddscostlychemicalstepstotheoverallconstructionofamolecule.Assuch,circumventingthisissuewillnotonlyimproveatomeconomybutalsoincreasetheoverallefficiencyofmultistepsyntheticsequences. DirectC-Hbondfunctionalizationreactionsarelimitedbytwofundamentalchallenges:(i)theinertnatureofmostcarbon-hydrogenbondsand(ii)therequirementtocontrolsiteselectivityinmoleculesthatcontaindiverseC-Hgroups.AmultitudeofstudieshaveaddressedthefirstchallengebydemonstratingthattransitionmetalscanreactwithC-HbondstoproduceCsMbondsinaprocessknownas“C-Hactivation”.1TheresultingCsMbondsarefarmorereactivethantheirC-Hcounterparts,andinmanycasestheycanbeconvertedtonewfunctionalgroupsundermildconditions. Thesecondmajorchallengeisachievingselectivefunctional-izationofasingleC-Hbondwithinacomplexmolecule.Whileseveraldifferentstrategieshavebeenemployedtoaddressthisissue,themostcommon(andthesubjectofthecurrentreview)involvestheuseofsubstratesthatcontaincoordinatingligands.Theseligands(oftentermed“directinggroups”)bindtothemetalcenterandselectivelydeliverthecatalysttoaproximalC-Hbond.Manydifferenttransitionmetals,includingRu,Rh,Pt,andPd,undergostoichiometricligand-directedC-Hactivationreactions(alsoknownascyclometalation).2,3Furthermore,overthepast15years,avarietyofcatalyticcarbon-carbonbond-formingprocesseshavebeendevelopedthatinvolvecyclometalationasakeystep.1b-d,4Thecurrentreviewwillfocusspecificallyonligand-directedC-Hfunctionalizationreactionscatalyzedbypalladium.Palladiumcomplexesareparticularlyattractivecatalystsforsuchtransforma-tionsforseveralreasons.First,ligand-directedC-Hfunctional-izationatPdcenterscanbeusedtoinstallmanydifferenttypesofbonds,includingcarbon-oxygen,carbon-halogen,carbon-nitrogen,carbon-sulfur,andcarbon-carbonlinkages.Fewothercatalystsallowsuchdiversebondconstructions,5-7andthisversatilityispredominantlytheresultoftwokeyfeatures:(i)thecompatibilityofmanyPdIIcatalystswithoxidants,and(ii)theabilitytoselectivelyfunctionalizecyclopalladatedintermediates.Second,palladiumparticipatesincyclometalationwithawidevarietyofdirectinggroupsand,unlikemanyothertransitionmetals,readilypromotesC-Hactivationatbothsp2andsp3C-Hsites.Finally,thevastmajorityofPd-catalyzeddirectedC-Hfunction-alizationreactionscanbeperformedinthepresenceofambientairandmoisture,makingthemexceptionallypracticalforapplica-tionsinorganicsynthesis
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thedevelopmentofmethodsforthedirectconversionofcarbonshydrogenbondsintocarbon ออกซิเจน คาร์บอน ฮาโลเจน คาร์บอนไนโตรเจน คาร์บอน ซัลเฟอร์ และ carbonbondsremainsacriticalchallengeinorganicchemistry . mildandselectivetransformationsofthistypewillundoubtedly จึง ndwidespreadapplicationacrossthechemical จึงละมั่ง includinginthesynthesisofpharmaceuticals naturalproducts , , , agrochemi cals พอลิเมอร์andfeedstockcommoditychemicals . traditionalapproachesfortheformationofsuchfunctionalgroupsrelyon prefunctionalizedstartingmaterialsforbothreactivityandselectivity อย่างไรก็ตาม therequirementforinstallingafunctionalgrouppriortothedesiredc-o CSX , c-n c-s orc-cbondaddscostlychemicalstepstotheoverallconstructionofamolecule.assuch , , , ,circumventingthisissuewillnotonlyimproveatomeconomybutalsoincreasetheoverallef จึง ciencyofmultistepsyntheticsequences . directc hbondfunctionalizationreactionsarelimitedbytwofundamentalchallenges : ( ฉัน ) theinertnatureofmostcarbon hydrogenbondsand ( 2 ) therequirementtocontrolsiteselectivityinmoleculesthatcontaindiversec hgroups .amultitudeofstudieshaveaddressedthe จึง rstchallengebydemonstratingthattransitionmetalscanreactwithc hbondstoproducecsmbondsinaprocessknownas " c-hactivation " 1theresultingcsmbondsarefarmorereactivethantheirc hcounterparts andinmanycasestheycanbeconvertedtonewfunctionalgroupsundermildconditions , . thesecondmajorchallengeisachievingselectivefunctional izationofasinglec hbondwithinacomplexmolecule .whileseveraldifferentstrategieshavebeenemployedtoaddressthisissue themostcommon ( andthesubjectofthecurrentreview ) , involvestheuseofsubstratesthatcontaincoordinatingligands . theseligands ( oftentermed " directinggroups " ) bindtothemetalcenterandselectivelydeliverthecatalysttoaproximalc hbond . manydifferenttransitionmetals includingru , กิจกรรม , andpd , PT ,undergostoichiometricligand directedc hactivationreactions ( alsoknownascyclometalation ) 2,3furthermore overthepast15years avarietyofcatalyticcarbon , , carbonbond formingprocesseshavebeendevelopedthatinvolvecyclometalationasakeystep . 1b-d 4thecurrentreviewwillfocusspeci จึง callyonligand , directedc hfunctionalizationreactionscatalyzedbypalladium .palladiumcomplexesareparticularlyattractivecatalystsforsuchtransforma tionsforseveralreasons แรกเกิด directedc hfunctional izationatpdcenterscanbeusedtoinstallmanydifferenttypesofbonds includingcarbon คาร์บอน , ออกซิเจน , หลอดฮาโลเจน , คาร์บอน ไนโตรเจน คาร์บอน ซัลเฟอร์ และ carbonlinkages fewothercatalystsallowsuchdiversebondconstructions 5-7andthisversatilityispredominantlytheresultoftwokeyfeatures : , .( ผม ) thecompatibilityofmanypdiicatalystswithoxidants และ ( 2 ) theabilitytoselectivelyfunctionalizecyclopalladatedintermediates ที่สอง palladiumparticipatesincyclometalationwithawidevarietyofdirectinggroupsand unlikemanyothertransitionmetals readilypromotesc-hactivationatbothsp2andsp3c-hsites.finally , , ,thevastmajorityofpd catalyzeddirectedc hfunction alizationreactionscanbeperformedinthepresenceofambientairandmoisture makingthemexceptionallypracticalforapplica tionsinorganicsynthesis ,
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