Amide Bond Activation: Concepts and Reactions

508 Pages·2022·23.684 MB·English

by  Michał Szostak

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AmideBondActivation ochrane Germ
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Amide Bond Activation ochrane G
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Concepts and Reactions iley Online L
Edited by Michal Szostak ibrary on [25/10/2022]. See the T
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Contents ochrane Germ
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Preface xv nline L
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1.3.1.1 HydrolysisoftheN–C(O)Bond 15 iley.com
1.3.1.2 CleavageoftheσC–NBond 17 /term
1111....3333....2222...312 RHROeeredagtecaurtnciovotaiimottoynemotoafflNtlthihuceesclCCeaoa1rpr9bbhooinlneyysllG1r2o80up 18 s-and-conditions) on W
1.3.2.4 OlefinationandEpoxidationReactions 20 iley O
1.3.2.5 EnolateandConjugateAdditionChemistry 21 nline L
1111....3334...344.1 RPMCoioinlsnygccmelOluelpasrieinoznenaiotsniuogasnnvRdiRaeOeaOacuctlteitloifioonnonsksMe222t3a42thesis 23 ibrary for rules of use; O
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vi 2Contents MSuobdsitfiitcuattiioonnaotfNAimtriodgicenR:eAsonnoamnecreicTAhrmoiudgehsHe2t9eroatom https://onlinelibrary.w
2.1 ISntetrpohdeuncAti.oGnlov2er9andAdamA.Rosser iley.com
22..22.1 SPtrroupcetrutrieaslPorfoApneortmieesric3A2mides 32 /doi/ by ibrahim
22..22..23 NThaetuorraeltiBcaolnDdeOterrdmerinAantiaolnysoisfAm33ideBondResonance 35 ragab - C
22..22..45 SEoxuprecreimsoefnAtanloEmviedreicncAemfoidreRsedu3c7edResonanceinAnomeric ochrane Germ
Amides 38 any , W
2.2.6 SpectroscopicPropertiesofAnomericAmides 43 iley O
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3 AmideBondActivationbyTwistingandNitrogen /term
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Modification 80 iley O
3.2.1 NonplanarAmides 80 nline L
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33..55.1 LNaocntpamlanAamrLidaectRamotaAtimonide9S4pinning 93 Contents vii https://onlinelibrary.w
3.6 CReofnecrleunscieosnan96dProspects 95 iley.com
4 Transition-Metal-FreeReactionsofAmidesbyTetrahedral /doi/ by ibrahim
IMnatercromBeldainagteestti,K1a0r1endelaVega-Hernández,MargheritaMiele,and ragab - C
4.1 IVnitttroordioucPtaiocen 101 ochrane Germ
4.2 SynthesisofCarbonylsfromAmides 102 any , W
4.2.1 AdditiontoCanonicalAmides 102 iley O
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CarlosR.GonçalvesandDanielKaiser iley.com
5.1 Introduction:ElectrophilicActivation 157 /term
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5.4 AmideBondFunctionalizationofActivatedTertiaryAmides 164 iley O
5.4.1 [2+2]-Cycloadditions 164 nline L
5555....4444....2333..21 SHCNtauyerdrcbelreooidonsiepcNlheRuicletceidlvAeueodcpCtdhiyioticnilloeosna1d7d110i66t8i8ons 167 ibrary for rules of use; O
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viii 6Contents TMreacnhsaamniisdtiactiIonnsiogfhtCsa,rCboonxcaempitdse,asnadndReAamctiidoenDser1iv8a7tives: https://onlinelibrary.w
6.1 IPnatorloadAuccotsiotan-Gu1z8m7án,JohnCorredor-Barinas,andDiegoGamba-Sánchez iley.com
66..23 HDiirsetocrtiTcaralnBsaacmkgidroautinodnof1C88arboxamides 190 /doi/ by ibrahim
66..33..12 MTreacnhsaitnioisntiMcIentasilgChatstaly1s9is0 193 ragab - C
66..33..43 OOtrhgaenroCcaattaallyytsicisan1d9P5romotedProcesses 198 ochrane Germ
6.3.4.1 Bases 198 any , W
6.3.4.2 BoronDerivatives 199 iley O
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6.5.3 UsingCarbonylandThiocarbonylHeterocyclesasActivators 213 iley.com
6.5.4 FromAmidines 214 /term
67.6 CRAmeofniedcrleeunBscioeonsndsEa2ns1td6erPiefircsapteiocntivaensdH2y1d5rolysis 221 s-and-conditions) on W
KazushiMashima,TakahiroHirai,andHarukiNagae iley O
7.1 StoichiometricReactions 221 nline L
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8 ALicatnivaaHtiioenaonfdATmejaidseKC.–ShNaBhondsbyNickelCatalysis 243 Contents ix https://onlinelibrary.w
88..21 EInsttreordifiuccattioionno2f4A3mides 243 iley.com
88..34 HTryadnrsoalmysiidsaotfioAnmid2e4s9 248 /doi/ by ibrahim
88..56 SNuezguiskhi–iMCoiyuapulirnagCoofuApmlinidgeosfA2m58ides 255 ragab - C
88..87 RMeidzourcotikoin–HanecdkRCeoduupctliivnegCofoAupmliindgesofA2m61ides 265 ochrane Germ
References 269 any , W
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99999....3124 PIPAFPPnaddddmte(((–rNIηzioNId3d)SH-eH–.1usCNCA-ct)ltH-Co(iB2oAatCu7antl-5i-albCyIlnilya,)2dstCM7iaesl3linycPiyhnzrleae)Cde(crIlaoPCRtsrar.s)olCC-ysCshls-ot-hCCuionapoutluSnaiun,plyagzliznuneodkgdfiG–ARSrMmueeazgiicyudotarekiyuosi–nrRaMs.2CCoi7yofr3aooAuksmsr-aCidCoerusopslsi2-nC7g4ooufpling nline Library on [25/10/2022]. See the T
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999...657 PVCRAoAfdaeommA-rfnPeiiicomddrEleueeuPinsssdsPceiPSeosdsS22n–I88N162P2H72r8e98C8c8aPtarelycsattainlytshtseSSuuiztuabklie–MfoiryCaurorassC-Croosusp-Clinogupolfingof s and Conditions (https://onlinelibrary.w
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10 Cross-CouplingofAmidesThroughDecarbonylation 293 /term
111000...122.1 PIDHnhoetntcrhoagardLbluiuomcntaiiyndoldenastHioa2no299o3W5feCiyclicAmideDerivatives 294 s-and-conditions) on W
10.2.2 SaccharinsandOtherCyclicAmideDerivatives 297 iley O
10.3 DecarbonylationofAcyclicAmideDerivatives 298 nline L
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x 1Co1ntents TTaralinnseitKioenraMckeiatnal,-DCiadtiaelryBzoeudyRssaid,NicuanloReMaocntitoenirso,oafnAdmides 307 https://onlinelibrary.w
11.1 IAnbtdreordruahctmioanneA3m07goune iley.com
11.2 RCeoamctpioounnsdInsvo3lv0i8ngAmidesasPrecursorstoOrganometallic /doi/ by ibrahim
11.2.1 RAacdtiivcaatlioRneac3ti0o8nsofAmidesviaMetal-CatalyzedC–NBond ragab - C
1111..22..11..12 RPhedoutocrteivdeoxCCrorsoss-sE-lCeocturpolpinhgileRCearcotsiso-nCsoup3l1i2ngReactions 309 ochrane Germ
11.2.2 Chelation-AssistedRadicalReactionsofAmides 316 any , W
11.2.2.1 Amide-DirectedC–HBondFunctionalization 316 iley O
111111111111......233333.....21112...221 ADRRCRVeeeaimicsaaartibicccnadtttonaiiienooolt--nnnDDCCsssi–ierfoIoHeunnffcntvAAteBcoermmotdleivnodiiFidddnnRueeagFnassluAidcvvzntimiiaicaacotaitinAαdolisoa-nemAnlsioazmia3dflasi2yiPtzn3iPlaeoorRntneaidaoclodkanufnyircUlstaoR3Onlrs2aasl5dectfitio3cinv2aNas3lstietrd3o32Ag24el8nke-noers 318 nline Library on [25/10/2022]. See the T
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11111111....4333...223..12 CCRCRtoee––oAafHHnecclrtkBBleiueonoonsncnnieseoddssnoFFfuuA33nn323m3cc843ttiiidooennsaavlliiizzaaaCttiiaoornnbavvmiiaaoRCyarlodRsisca-adcliocAuadplsdliintig3o3n1329 s and Conditions (https://onlinelibrary.w
12 WeinrebAmideasaMultifacetedDirectingGroupinC–H iley.com
Activation 339 /term
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12.2.2 Co-CatalyzedReactions 344 iley O
12.2.3 Pd-CatalyzedReactions 346 nline L
11112222....2234..45 RIWCrho-eCn-iCnacltaruaetlasbyilozyAenzmdesdiaRdnReedae-DcaOtciituroietonclnosteosdk3C53(453s26p23)–HActivation 359 ibrary for rules of use; O
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13 XCoinmHpountga,tiPoeni-aPleSitXuidei,eZshoi-fXAinmQidien,Ca–nNdSBhounod-QAicntgivZahtiaonng 365 Contents xi https://onlinelibrary.w
1133..12 IGnetnroedraulcMtioencha3n6is5msofAmideC–NBondCleavageand iley.com
13.3 CDoemrivpautitzaatitoionnalS3tu6d7iesontheMechanismandSelectivityofLewis /doi/ by ibrahim
13.3.1 CAocimd-pMuteadtiiaotneadlNStuucdleieospohnilitcheSuMbestcihtuatnioisnmoafnAdmSiedleesctiv3i6ty8of ragab - C
13.3.2 CLioHmMpDutSa-tMioendailaStetuddTierasnosnamthiedaMtieocnhan3i6sm9 andReactivityof ochrane Germ
Zn-CatalyzedEsterificationofAmides 373 any , W
13.3.3 ComputationalStudiesontheMechanismofAmmoniumSalt-Mediated iley O
111333...443..14 CCCHMEAsooosyetymmmdetmarrppplai-mfiuuuzCcitttenaaaaatttttotraiiiiiloooolcyynnnnsAzaaaioselllldfcoSSSoAftttChuuuAmrodddomliyiisydeesisossed-inscsooeonnsotuhf3ttpehhN83leeM1i7-nS5MMgeuceeolhfccfoahhAnnaayminnsliimiAssdmmmeasniaoddnfe3dOR8reS0g3aea7clent8icovtciitvayittaoylfyoNtficiT-rCaantsailtyiozend nline Library on [25/10/2022]. See the T
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11113333....4444....5342 CCCCSCNuoooo–i-zNmmmmCuppppakBtuuuuioa–ttttnlMaaaaydttttziiiiiooooeyAdnnnnacuaaaaCtillllrv–aSSSSaNttttCtuuuuioBoddddunoyyyypnoooooldfinnnnnTAttttgwhhhhcoeeeetifisvMMSMtAeatrdeeetmuicccoAcihhhndtmaaaueonnnsrifiiiedsssA–emmmA3sm8caooi7tnffdi3vdPNe8isd8tiSy--eCCRl3eaae9cttla1ataillvtyyiizzoteeynddsohfiNpio-Cfatalyzed s and Conditions (https://onlinelibrary.w
Suzuki–MiyauraCouplingofAmides 395 iley.com
13.4.6 ComputationalStudyontheMechanismofPd-Catalyzed /term
13.5 TROreuaftenlroseaonmkcieds3a9ti83o9n9ofAmides 398 s-and-conditions) on W
14 EstersasViableAcylCross-CouplingElectrophiles 403 iley O
OmidDaneshfarandStephenG.Newman nline L
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14.3.2 C–HBiarylCoupling 409 articles are governed by the applicable C
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