Table Of Content

D ow nloaded from https://onlinelibrary.w iley.com /doi/ by ibrahim ragab - C AmideBondActivation ochrane Germ any , W iley O nline L ibrary on [25/10/2022]. See the T erm s and C onditions (https://onlinelibrary.w iley.com /term s-and-conditions) on W iley O nline L ibrary for rules of use; O A articles are governed by the applicable C reative C om m ons L icense D ow nloaded from https://onlinelibrary.w iley.com /doi/ by ibrahim ragab - C Amide Bond Activation ochrane G erm any , W Concepts and Reactions iley Online L Edited by Michal Szostak ibrary on [25/10/2022]. See the T erm s and C onditions (https://onlinelibrary.w iley.com /term s-and-conditions) on W iley O nline L ibrary for rules of use; O A articles are governed by the applicable C reative C om m ons L icense D ow nloaded from https://onlinelibrary.w iley.com /doi/ by ibrahim ragab - C ochrane G erm Editor AllbookspublishedbyWILEY-VCHarecarefully any , W produced.Nevertheless,authors,editors,and iley O PRD7NUCo3rueeSovpwtWAfeg.araeMarrIrrtmiksmrc,ehUaenNagnnleJStiS:vt0zo©re7oefrs1eCsMt0tiaht2kiycehmailsStrzyostak pctipiLnnooirubaonbmbrdctaelaeviirsnfideyrhndrueoeetereftrdahnCodliatofnodltnyeestngrthbtrroaaeoeeittslsreiswessnm.oaCabRrercaornecrooadauttknsdhrNs,taee,dottrrieh.asn:i.tetaacaerlpi,muenpidlfaslloiiudenmrsvdmgtiarsftayaoehttdriiiosotnnobsok,oeke,p nline Library on [25/10/2022]. See the T erm BAfBtTtrhhirhobeiictsemlaiDispoDtheatguheulrLboutaeilsgbpticBuscrhhcaareiehircttyrieiNoiesnCncNahfaotoaitiLrrnoatdmiinlbootfaahrngoltaebuariroiliDytbnbnh.lgieiipbo-usuilttnibbhso-olcetPiohhksuhkeebeklidiscliaabstvytisaoinlaDbaleta s and Conditions (https://onlinelibrary.w Ndaattaioanrealabvibaliiloabgrleafioen;tdheetaIinletedrnbiebtlaiotgraphic iley.com <http://dnb.d-nb.de>. /term ©6Atr9al4l2n60rsi92lga3hWtiWtoseniIrnLeihsnEeetYriomv-Voe,dtChGH(eeinrrGmclalmunandbgiyuHna,ggBethos)so.csNhesootrfp.a1r2t,of s-and-conditions) on Wiley O thisbookmaybereproducedinanyform–by nline L pmmftrrhoaeaodmactehnomtisphnr–aeeirnnpklatousin,rnbgegtlurti,scaamh.nguesiercsmsrew.oidtiRfittiehelnmdgotiuo,hsttorieswrtrrbearaodinntoytnsekloana,tmtehpeveedeesrrni,mnwtioshsaieonn ibrary for rules of use; O ncPeeoTyoPPBroipnuDotnebsotFssipkIdIeISSeSteIBBStcBriiNBNenNfidN:g::c99:9au7797lnl8S878yp-t-8-3r3r3m-ao--3-55i5ta-v2e252rec77k27,t--7e-e3C88d-d4383h8a030be3s202yn1624snl--u5-a28a4-cwi1h,.I,nadreianottobe A articles are governed by the applicable C reative C om m ons L icense D ow nloaded from v https://onlinelibrary.w iley.com /doi/ by ibrahim ragab - C Contents ochrane Germ any , W iley O Preface xv nline L 1111...122.1 PIGTBnyareltirendrarogemdJre.auedFltcueLPtlriartosoocnontpaf,eamYArntudsimneaSsiEsdco.oeMfDpBBoueord,inaeddnl1gdSeDdyBissrLttieaaomncrttisaMomf.noSsrtoA3l3mtzidicDistortion 1 ibrary on [25/10/2022]. See the T erm 11111.....22332....4213 TBLNNRRwaoee--caacnivtosccdsattto.emiiLrvvOddeiis-ttinApyyngrmaoo5tothffitidoosBth,ennrBeiaBdotLagin7oasedincdctAiaaLtmnynadcgaNtlnMaedimste,rptosahKgnyeadl1naMS5tipeoe1ancs5tuarnroedsmcSoetprniutcscPturor1ap4leErtffieesctosfoBfridged s and Conditions (https://onlinelibrary.w 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 A References 24 articles are governed by the applicable C reative C om m ons L icense D ow nloaded from 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 222222......323333.....71222..21 TTRARSENhhleemi2aaeemiccoRdAttirniieeenvvsaatiioitcttcmiyytoai4oaonle6tfnrSRitAstchrenuEeaocc5ffAtmt3ueinocreontermsisca(e5ASnr0Nidmc1AAi-dTmmeyspiiddeiecP5iNr0toiiectsreosogsfeeMsn)od55e36lAnomeric nline Library on [25/10/2022]. See the Term 22222.....34333....3333...123 AHOCTRRheeomtEhafenReicecdRrtOrleieuooHnNldBnceEioseRnoRsnegfOdat6RchNS63teec8imoRinsneasYsair–okcoσntsf*ioNNRnXe6-sAa6Aclntki6ooo0xmnyse-:NrTic-hAEemffHeinEcotRaaOmnNdidRReeesasocnt5ia8onnce5in7HERON s and Conditions (https://onlinelibrary.w iley.com 3 AmideBondActivationbyTwistingandNitrogen /term 33..12 INPYnuyotkrnraoopmdOlauitdnacantailiroizaAnanmtdioi7Tdn9oemso7thh9iaktoAOrhewSaudffiacientlyStableforChemical s-and-conditions) on W Modification 80 iley O 3.2.1 NonplanarAmides 80 nline L 333...322..23 AATChhpmiepoimlnaicomiacAtaidiloceSinsdtastob8iAl38itm5yionfoNAitcriodgse:nArPtyifiracmiaildHalelAicmesidCeosmp8o3sedofBicyclic ibrary for rules of use; O A 33333.....34333....1323.1 CAAIBHnroppetinteppderfllgroaiieccocrhaaomtttieloiiiaaoogntdnnoi-osmStnoou9eaf2bArlHssPrtteiritlefiu9ifcc0teaeiraldelPnBHecipeectlyoiicdcfleeiBscsiacaAynsmcdIlniiSnchtorβiba-AAintcdomirdMsisnoiomf8Api8c5cs3id-Ms9D08M52/MDMX articles are governed by the applicable C reative C om m ons L icense D ow nloaded from 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 444444......232444....2321 VISRAEGsyalemeoenrcnlciateieatnhntrrtieeoiatoossplUninhCssoiooo1elffifsn1cTtC9coheAefateprmrAatbAmhiodmenie1ddiy2drLel8a-esiLlnSaiIkkntnraedtugeCceNrtmoAu-mArecedltpkiiovaoaut1xten0yisoda7nms1id111e522s98fortheSynthesisof nline Library on [25/10/2022]. See the T erm 44445....5464..34 SSCREAyyleocennftnceittvtchhrrlaeeeoutnsspiscioiihsseonisoonloiffscfHAa1AAnme5mmtd0eiinidrOdoeeue-cLsBtylicowoklnoeeitkdshCFoDu1m1in45ffpc50etoiruoennnadtlsEizlae1ctit3or7onph1il5ic7Agents 144 s and Conditions (https://onlinelibrary.w CarlosR.GonçalvesandDanielKaiser iley.com 5.1 Introduction:ElectrophilicActivation 157 /term 5555....2333..12 HHIEnaiitssrrttloooydrrEyyuncootdffieottahhnvee:oEAArlscceittcniitvvrEaaottlpiieoohcnnitlriooocffpASTheecilctriitocvinaaArdtyimaorAniydmoeAfiAmdAecimstdievidsa1et6iso01n51951859 s-and-conditions) on W 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 A 55555.....56455...231.3 HKSCARyeoemenftnteoeticdhrnrleoeeuenassBScitisooeyosmannnntdshdNF1euF8su1i1cu8nsln0cetcoi1tpoi7ohn9nialaleilsziazati1toi7on1nooffAHcteitveartoecdyScleecsond1a7r6yAmides 175 articles are governed by the applicable C reative C om m ons L icense D ow nloaded from 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 666666......344433.....52144..43 CTTOTBHrrroateaaahnttnnnaeedlsssrryoaaaPsmmmgt2reoaiii0ndddnm4eaaadootttiiiuPtoooesrnnnroCsmoobaffytoAAa2tthl0eccy1retts-iiivvFPsaarrtteeeeev2ddiP0oSS0ruuuosbbcFessstturrsnaaecttseetissoUU2n0ass3iilnnizggatMFioluentoaorliflditcehCeasaAtaamnlyisdtes 205 nline Library on [25/10/2022]. See the T erm 66666.....55445....1243 ROTTTACrrreauxaaadtixnnnaduilssslacyiaaatatsimmmirtvvsyeiiiedddTTaaa2r2rttta0iiia0ooon9n7nnnssaaoowmmffitAAiihddccaaAttttiiivvitooyaannptteeicdda22SSl11uuS21bbussbttsrrtaarttaeetssesUWsiit2nh1go1uOttPhreormProotemrsotoerrs 208 s and Conditions (https://onlinelibrary.w 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 7777....5243 ACNCahc-βtteai-lvHlaaytyttieindcdgrRoAAxemyuaecxittdihiloeiyasnlrsyA2am3t2i5t2dh8eesNi2tr3o2genAtomofAmides 234 ibrary for rules of use; O A References 237 articles are governed by the applicable C reative C om m ons L icense D ow nloaded from 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 iley O 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 erm 999...657 PVCRAoAfdaeommA-rfnPeiiicomddrEleueeuPinsssdsPceiPSeosdsS22n–I88N162P2H72r8e98C8c8aPtarelycsattainlytshtseSSuuiztuabklie–MfoiryCaurorassC-Croosusp-Clinogupolfingof s and Conditions (https://onlinelibrary.w iley.com 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 11110000....3433...312 OCNNot--hAAnecccrlyyuAll-ssGacioyclnccuhltiaacrr3Aii0mnm5iAdidmeesisde2s39082302 ibrary for rules of use; O A References 305 articles are governed by the applicable C reative C om m ons L icense D ow nloaded from 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 erm 11111111....4333...223..12 CCRCRtoee––oAafHHnecclrtkBBleiueonoonsncnnieseoddssnoFFfuuA33nn323m3cc843ttiiidooennsaavlliiizzaaaCttiiaoornnbavvmiiaaoRCyarlodRsisca-adcliocAuadplsdliintig3o3n1329 s and Conditions (https://onlinelibrary.w 12 WeinrebAmideasaMultifacetedDirectingGroupinC–H iley.com Activation 339 /term 111222...122.1 RIWJanuytea-riCobndraraeuttabcaltyAiDzomaensdidaRen3e-d3Da9cDitreieobcnatesbdraCt3a(4s0Mp2a)i–tiHActivation 340 s-and-conditions) on W 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 A References 362 articles are governed by the applicable C reative C om m ons L icense D ow nloaded from 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 erm 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 11114444....3123.1 DMIEnaeitrzcrlooayrdrWbouokconit–riykoHlnaientcivkt4eh-T0eC3yCopureopCslsion-ucgopoulifpnAlginrygl4oE0f8sCtearrsbox4y0l8icAcidDerivatives 404 ibrary for rules of use; O A 14.3.2 C–HBiarylCoupling 409 articles are governed by the applicable C reative C om m ons L icense