Abstract
Superelectrophiles are reactive species that often carry multiple positive charges. They have been useful in numerous synthetic methods and they often exhibit highly unusual reactivities. Recent advances in superelectrophile chemistry are discussed in this review.
Highlights
F(Socrheexmame 1p)l.eW, nhitirleonthiuemnistaroltnsieuxmhiiboint h(1ig)hiserrerecaocgtniviziteidesaisnastsrtornonggerealecicdtrsoapnhdileth, iasnwinascrienatseirnpgredteedgrbeye Ooflaphroatsopnraotitoonsollevaadtsiotnooafnthioenniwtriothnigurmeactaertiopnos(i1t)ivine tchhearsguepe(ir.ae.c,id2iacnsdolu3)t,ioannsd(Scochnesmeqeu1e)n.tlWy,hhilieghtheer nelietrcotrnoiupmhiliiocnre(1a)ctiisvrietyco. gnized as a strong electrophile, an increasing degree of protonation leads to an ion with greater positive charge (i.e., 2 and 3), and higher electrophilic reactivity
These trends were observed in several types of N-heterocyclic ring systems, that is sites with sizable positive charges tended to undergo conjugate addition with aromatic nucleophiles
Our group described a superelectrophilic reaction leading to aromatic imides (Scheme 26) [76]
Summary
1. IntIrno1d9u6c4t,ioSntaskun published a report describing the acid-promoted cyclizations of β-ketoamides wpKdt(pihaitnnhhtnriiehnicgveiosrdtseoayhhotfuotrowcllopiIKrgvynroonbaemrcinawnenssre1ytoilaeea9gioccierorcndt6lcrrvieiind4tkntzdreer—,cowetaidorSeytcrutphpiritsocabmtoamrahlrhwelsinsniezedektil)hmeadidguoop[cdetir1inun,iiraanelo]dboebat.pa[netytirl2teuDhcoes)ee]qaO.ben.ruLn[tuylTFa1lirheiaiottso]ihowvahni.hhnriobnaagseDiienaslsccndcexste—euioahnarmanprconvetmoitirrnscneeedoeroeepnedrgpftpdmctlsooHeaottetoosr,uehoqwou2fstndderSiuledbmaidsviiOltialeeseeviraeitsns4coftlaec,sautiaLnlsorortiretre.tuioirnibtunTewopwhdAitmnonhnheiiaehfls—irgioCsslsstaeifaht,aoclconxhc3loeibfHcrtp.ietnsedsentaAa2ehawmceiSncrccetexOvrdimaotepdhioβseneov4ti-endd-rtbpiwocktidooiruihtibetareonihfmantshssmaoeentAaiofthlargcituoefvtlsmeiahctChromoeett1teeininldrhdd9ro3o—iw.ce7enrucptor0e,yhAamonh(saelcsa1fevixclbt)lsaistmtepizyaiihductrvnaalhseeiOgtrtniniscetteigoβhldoihgaiaeenn-cneeachssktsodstnotsseiinaewuuonivithsndvnofppiemsitdeβageerititrneremhrrh-csosakavewobilinccyoeoowde1iaitgnfldsd9eeosovetso7,ilairircecp0nnmlkswceamseusigetauciorerbrgdeidfodmlsrdygodueeipowsrnesitOhsumaisbga(hoaitltb[enleaeehln2tiltsdddhncoeess]t,. Gnized as a strong electrophile, an increasing degree of protonation leads to an ion with greater positive charge (i.e., 2 and 3), and higher electrophilic reactivity. These types of actiSvcahteemdesp1.eScuiepseraerleecktrnoopwhinlicaascstuivpaetiroenleocfttrhoepnhiitlreosn—iuimonisonc.apable of reacting with exceptionally weak nucleophiles [3,4]. In the case of nitronium ion superelectrophiles (2 or 3), these speciTeshhesaevetybpeeesnosfhaocwtivnattoedresapctecwieitshadreeakcntiovwatnedasasreunpeesrealnedctarolkpahnieless(—inicolunds icnagpmabeltehoafnree)a[c3t,i4n].gSwinitche Oexlcaehp’stioinniatilalyl rwepeaokrtsnuwchleiochphfoilrems [a3l,i4z]e.dInththeecocnasceepotf onfitsruopnieuremleicotnrospuhpileircealeccttivroaptihoinle,sth(2eroerh3a)s, tbheeesne espxteecniessivheawveorbkeednonsheoiwn nthtios arreeaac.t wThitihs idnecaluctdiveastnedumareernoeuss asnydntahlektaicnemse(tihnocdluodloinggiems wethhiacnhe)ut[i3l,i4z]e. Have described the activation wowf iwro.mnd-pbia.csoemd/jocuartnaally/mstoslebcuyleas mechanism similar to superelectrophilic activation [13,14].
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