PDF Publication Title:
Text from PDF Page: 006
Catalysts 2020, 10, 762 6 of 15 experiments, n-heptane (lower neurotoxicity than n-hexane) and scCO2 were chosen as solvents for CaCaCtatlyaylsytst2s0202,01,01,0x, xFOFORRPEPERERERERVEIVIEIWEW 6 6o6ofo1f616 CaCtaltyaslytCsat2sta02l2y0s2,t0s1,021,0x2,0Fx,OF10RO,RPxEPFEOERERRPEREVEIVREIWREWEVIEW 6 o6fo1f616 of 16 pCrCaotaatdlaylusytscstst220e02x200,t1,r10a0,cx,txFiFoOOnRRPfPErEoEERmRRREtEhVVIeEIEWpWost-reactionmixtures. 66ooff1166 CCaatatalylysststs22002200, ,1100, ,xxFFORRPPEEERRRREEVVIEIEW CaCtatlyalsytst2s0202,01,01,0x, FxOFORRPEPERERERVEIVEIWEW CaCtatlaylsytst2s022002,01,01,0x, xFOFORRPEPERERERVEVIEIWEW 66ooff1166 6 o6fo1f616 6 6ofo1f616 CCatatlaylsytsts2022002,01, 01,0x, xFOFORRPEPERERREVEVIEIWEW CCaatatalylysststs22002200, ,1100, ,xxFFORRPPEEERRRREEVVIEIEW 6 6ofo1f 616 66ooff1166 Catalysts 2020, 10, x FOR PEER REVIEW 6 of 16 2.2..2S. cScocpoepeofoSfSf uSububsbtsrtartaetsesInIvnvevsetsitgiagtaitoinosns s 2.2.2S. cS2oc.p2oe.pSeofcooSfpuSebuosbftsrStarutaebtsetsIrnIavntevsetsIigntiavgteaisottiniogsnastions 22.2.2.2..2..SSccoopeoffSuubbsbststsrtrtararataetetsesesIsnInnIvnvesevststeitigsgigtaiatgitioiaontnsisosns 2.2..2S. cSocpoepeofoSf uSbusbtsrtartaetsesInIvnevsetsigtiagtaiotinosns 2.2..2S. ScSocpoepeofoSf SuSubusbtsrtartaetsesInInvnevsetsitgiagtaitoinonsns 2.2..2S. ScocpoepeofofSSuubsbtsrtartaetsesInInvevsetsitgiagtaitoinons s 2 2 . 2. 2 . . S S c c o o p p e e o o f f S S u u b b s s t t r r a a t t e e s s I I n n v v e e s s t t i gi g a a t t i oi o n n s s 2.2. SHcHoapvaevinoifngSgouopbpstittmriamitzeisezdeIndtvhtehesteirgeraetcaiotcintoisonnananddexetxrtarcatcitoionncoconnddititoionnssininhhanandd, ,wweehhavaveestsutuddieidedaascsocoppeeoof f HHavaivninggopoptitmimiziezdedththeereraecatcitoinonananddexetxrtarcatcitoinoncocnonddititoinonssininhahnadnd, w, weehhavaevestsutuddieidedaascsocpopeeofof HHavaivnHignagovpointpigmtimoizpieztdiemdtihztehederertaehcaetciotrienoancatnaiodnndeaxentxrdtarcaetcxiotirnoanctocinondnidctiotinodsnistiinoinhsahnaindn,dhw,awnedeh,ahwvaeveshtasutvdueidesidteudadaisecsdocpoaepseocofopfe of Haavvininggoopptitmimizizeeddththeerereaacctitoionnaannddeexxtrtaracctitoionnccoonndditiitoionnssininhhaanndd, ,weehhaavveesstutuddieieddaassccooppeeooff Haavvininggoopttimimizizeedtthheerreeaaccttioionnaanndeexxttrraaccttioionnccoonndititioionnssininhhaannd,,weehhaavveessttudieiedaassccoopeeooff HHavavivniingngoopoptpitmtiimiziezdedththehereraecatcitotinonanadndexetxrtarcatcictotiniooncnoccnoodnnidtditoiitnoiosnnsinsinihnahhnadann,dwd, w,eweheahvhaevaevstesutsdutuideideideadascasocspocepoepofeofofolefins, ololelfeifnHinsnsH,as,vamvimnaingiangiolnlyopolypteitmleiemlcieztcireztordrenondn-tn-hdt-hedefeferifcecriaceceicianetcntintto,itono,nneneauenaututndrtdadarelaxelotxrortarcdadtcdoitononiononanantacitnocingnonoggngdsditsyiyitoryrioneoernsenensesisnei,snh,inhainabndobod,ror,wyrwlylealetahitvhaievevaeveceosctuousutupupudplpldilnelnidenegngdgawawsictsihocthopo1pe1eioniofonf oloelfeinfiHoHsnH,lsaea,mvafvimvinanisinagn,iglnomoylopyapetiltnemeilmceyitzczritezeoerdedlnoed-nctdht-tredheofeinrfceir-icdeaeaincacetctfni,itotci,nonienenauetnantu,nrdtandrleaexexluoxtrortaradcaclodtciotnoiraontnadicntoicgnongandstdtistytnititroyogieonrnensentsyisien,irsne,ihnhiaenanbsnd,obd,riony,wrlwyaebelteaoihvtrhiayevavleavectoecisvuotsueputudlpcidinloeignudeddgpwalaiwisnstcshigotochopw1pe1ieitnohiofnf1 in o o l e l e f i f n Hi n s H a s , , a v m v i m n i a n g a i g n i o n l y o p l y p t i e t me l i e ml i e c z c i t z e r t o r d e o d n n t - h t d - h e d e e e f r i f e r c i a e c i e i a c e n t c n i t t o i , t o n , n n n a e e a n u u n d t r t d a r e a l x e l x t o r o t r a r r a c d t c d i o t o o i n o n n a n a t c i t o c n i o n n g n g d d s i t s t i i y t t o y i r o n r e n s e n n s e i n e s i n s , h , i h a n i n a n n b d b d o , o r , w y r w y e l a l e a t h i t h a v i v a v e e v e c e s c o t o s u u t u p u d p l d i i l e n i i d e n g d g a w a ws i c s t i o c h t h o p p 1 e 1 e o i n o i f n f ooleleffininss,, maaininlyly eeleleccttrroonn--deefficicieienntt,, nneeuttrraall oorr doonnaattiningg ssttyyrreenneess,, inin bboorryylalattivivee ccoouplilningg witithh 11 inin moloealfieinfnilsny,s,emlmeaciantirlnyolyne-ledelcetcfirtocrnoie-ndn-edt,feinfcieceuinetnr,ta,nlenouerturdtarolanloarotridnodgnoanstaiyntirgnegnsetsystry,erineenbse,os,irnyinlbaobtirovyrelyalctaiotviuevpecloicnuogpulpwinliigntghw1witihinth1[B1iMninIm][OTf] [oB[oloBeBMlfeMiIfnmimiInsm,]s]s[,]mO[mOTaTiTaTafn]ifnl](yTlT(yTaebalelbleceltec4rto)4r.ono)T.Tn-dTh-dehefeirfceiricaeicanetcnti,toti,nonneouefofoutf1r1tar1wlawloitoroihtrhdbdorbronormomnamtaoiotn-oio-i(ng(-2(g(gb2sb)t)syt)t)oyryrorerrnreflnefulseuo,sror,ionri-o-ns-busbobuborosbsyrtsiylyitatililutataiuetvdidevede(c2(oc2)ouo)c)u)pstpslsyitlnryriengernegegwnenesweistihntihnp1ap1rianarina [oBo[olMBelMfefIifmn[iInBsms],sM[],Om[IOmTmafTiai]nfi[n](lOTyl(yTaTebfal]ellbel(ceclTet4crat)4orb.)onlT.en-hTd-4ehde)efef.rifeTcriaiceheciaenentcintotr,iteno,nanceoetueufoiuotf1rnta1arwlalowlifothior1thrbdwdrdboirontnmhonamtatobit-nroi(ong-2(mgb2s)botsy)o-t(yro2errbfnenl)nufelsesou,sro,oirfn-ilosnu-ubsobuorosorbrty-rsisyltltauauiltatbeuitvdvseitvedi(et2uc(c2oce)coudu)supt(spyl2tirlcynie)nrgnesgentwysewrisitenihtinhpe1asp1raianrianpara o[B[olBeMlfeMifnIimInsm,s],[]mO[mOaTiaTfni]fnl]y(lT(yTeaalebeblceltcer4tor4)on.).nT-dT-hdehefeifrciericeaianeccnti,toi,onneoueofutfr1tar1alwloitorihtrhdbdobronornoamatiotnio-ng(-2g(2bsbts)yt)oyroerrnefnelfulseu,oso,rinorion-s-bsubouborbsyrstylitatliuatiuteviedvede(c2(oc2couc)u)pspsltiytlnyirngergenwnewesistihtnihn1p1paiarniarna [[BMIIm]][[OTff]]((Taabblele44))..Thheerreeaaccttioionnooff11witithhbbrroomoo--((22b))oorrffluluoorroo--ssubbssttititueed((22cc))ssttyyrreenneessininppaarraa [B[MBMImIm][]O[OTTf]f](T(Tabalbele4)4.)T. Thehereraecatcitoinonofof11wwitihthbrbormomo-o(-2(b2)b)ororflfulouroor-os-usbusbtsitiuteuded(2(c2)c)stsytryerneensesininpaprara (p[TBp[oaBMosbMistIlimetoIimon]4[n])Ol[.eOlTdeTfd]thfo]t(eoT(TaEr(ebaE)-alb)ae-cllaekt4li)ke4o.n)enT.nyThylohelbfebor1eoraoerwconatcnaitotaihenotsenbsowrfowoif1timh1twhhwoihti-igh(it2ghbhryb)oyiremoilemrdolds-ofl(s-(2u(T(b2oTab)rba)oblero-lserf4ul,f4ulb,euosnerotntorirt-toyrsu-yus2eub–2dsb3–ts)3(i.t2)iu.AtcueA)pdespdt(ply2i(lc2riac)ecta)snitotsieyontsryneorinenofnefeseplesailnceritcnarptoraponraoan-rsa-ition led p[poB[BsoMiMstiIitomIimno]n[]lO[eOldeTTdft]fo]t(oT(TEa(aE)b-b)la-elaek4lek4)n.e).nyTTlyhhlbeeobrroreoeranoaccnatitaoieotnsenswoowfift1ih1thwhwihitgihithghhbybriyroeoimlemdlodso-s(-2T((2bTab)ba)lboeolrer4f,l4fule,uoneorntrortoy-rs-ysu2u–b2b3–ss)t3.it)tiA.utuAepedpdpl(i2(lc2icac)ta)istositnoytynroreefonnfeesleslicenitcnrtporpanoar-nraa- p[opB[sBoMiMstiIpotmIinmo]sn[l]iOe[tlOideTodTnft]oft]l(oeT(dETa()Eabt-)obal-elake(l4Eek4)n.e)-y.anTlTyhkblheoebnroyerorealnoacbantcoitaoeirtonsoenswoaowfittfe1hist1hwhwihgtihithghhbyhbriyoiregoimlehdmlosdyo-s(i(-eT2(l2baTdb)as)lboe(olrTe4rfa,l4fbuel,luoneortno4rtyo,-rs-ye2usnu–2bt3b–sr)yt3s.it)tiA2.ut–uAep3edp)d.lp(iA2cl(i2cacp)ctaip)sotlitsnioytcynraoertfoenionfenleseslcoientifcrntoperplanoera-ncart-aron- [pBp[oBMosMsiItimitIoimo]n[n]O[lOelTedTfd]ft]ot(oT((TaE(abE)bl-)ea-lael4klk4)e.)en.TnyThylhelbebroeoraeoracontcnaitoatioentesnsowofwfi1ti1htwhwhihtihgtihghbhbryoryiomeiemldoldos-(s-2(T(2bTba)ab)oblorelerf4lf4u,l,ueoenornortrot-yrs-yus2ub2–bs–3ts3i)t.)iu.tAueApdepdp(pl2(il2cic)aca)tsitosiyotnyrneroneofnefeseelseilnecinctprtorpaornaanr-a- poossititioionnleledttoo((E))--aalklkeennyyllbboorroonnaatteesswitithhhhigighhyyieieldldss((Taabblele44,,eennttrryy22––33))..Applilcicaattioionnooffeeleleccttrroonn-- popsoistitoinonleldedtoto(E()E-)a-laklekneynlybl obroornoantaetseswwitihthhihgihghyiyeiledlsds(T(Tabalbele4,4e, netnrtyry2–23–)3.)A. Applpicliactaitoinonofofelelcetcrtorno-n- twpowpoit(tosoihEitsthdhdi)itod-driaonorwlwanklweielndeingngdytgogtlorgr(borE(ououE)urpu-p)ao-pspslankslkekausnetucenyhcsylyhalbwsabobs–i–orotCo–rhrConoFnhna3F3 t(a(i3e2gt(sded2hsd–weye–wi)eitieh)atlhladshslohshisgoig(ghgTagahvyvaevyivyebeeielalaednalaldsn4nes,(xeTe(cxTanecbaletelblbrlelelylne4ntnt2,4tc–,eoc3nenon)ntvnv.rtyeverAryre2srpi–i2sop3i–inon)3l.ni)oc.AfofaApf1t1ip.1opTl.T.nilTlcTriacrontnafinstntsoi-e-sonobl-neobocrorofoytrfrelylaoaleletanlicieto-ticicrnwonotornonoitfofon-hf-drawing wpwpiotohsistisdhtiwirdtoiarionwtanhwlidenlidedrgnadgtwgotrgoion(rEu(ogE)pu-g)asp-rlalsosklukuescunenphnycyshylaslbsbuabosc–orhrC–orCFaons3nFa(3tat–2e(tCd2sesF–dswe3–w)(iei2tai)hdtlhas–hloeshi)ogigahaglhvasyeovyieiaglelndaldvnsesex(eTc(axTeanclbabelebelelexnlectn4e,4,ctlo,lecenenonvtnttrtevyrcreyos2rins–2–ovi3–3noe)3)n.ro)s.AfoiAo1fpn.p1pT.plolirTlfcairac1natat.sintoT-isbonr-onabornoyofsrfly-eablelteaeoilcoectritcynortlonoraontfoin-of-n of p w wp o i o s t i h i t s t h i d i t o d i r o n a r n a w l w e l i d e n i n d g t g o t g o g r ( o r E ( o E u ) u - ) p a - p s a l k s l s k e s u n e u c n y c h y l h l a b a s b o s o r – o – r C o C n F n a F 3 a t 3 ( e t 2 ( s e 2 d s d w – w– e i e ) t i h ) t a h a l h s l h s i o g o i g g h g h a y a v y v i e e i e l e a d l a n d s n s e ( e T x ( x T c a c e a b e l b l l l e e l l e e n 4 n t 4 , t c , e c o n e o n n t n r v t y v r e y e r 2 s r 2 – s i o 3 – i o n 3 ) . n ) . o A o f A p f 1 p p 1 . p l . T i l T c r i a c a r a t a n i t n o s i o s - n b - n b o o o o r f y r f e y l l e a l e a l t c e i t o t c i r o t n o r n o n o n o - f f - witithhdrraawininggggrrooupssssucchhaass––CFF33((22d––ee))aalslsooggaavveeaanneexxcceellelennttccoonnvveerrssioionnooff11..Trraannss--bboorryylalattioionnooff wwitihtdhrdarwawinigngrgoruopuspsuscuhchasas–C–CF3F(32(d2–de–)e)alaslosogagvaeveananexecxeclelellnetnct ocnovnevresrisoinonofo1f .1T. rTarnasn-sb-obroyrlyaltaitoinonofof g1wr1woiwittwiwiuhihtitthdpihdihtdrshrhararaswawauwiicwnwneieiehngagaegkakaglksklgrgyrlolro–youoduCupdodopFpsnonssananast(utasui2iutnctncdihcgnhng–hga–e–sasC)C–s–C–aHC–ClH3CsC3Fo3gF3Fg3(r3g3grg(2o2o(rad2uduouvd–pupu–pe–espsps)e)as)i)iaianliaiailsnslemomsoxomegecgtegeaegeatvalval(ve2e2(enfaf2a)nftafan)ononocerorxexrnpcpxpceavacapelreralealalalerelanese(n(2int2t(og2t2tcn)go)co)on)oponnvopopvfovesoes1rieieirst.tstrsitsotstoTioioinoronononasnsnsnonsosrofosferf-f1s1ebu.u1us.soT.lulTtrTrlelerytardradelnandansistn-ns-ibob-n-nbobtonhrotreyheheryoylyelfadalta1dedeteiitsoseoiwinosrnrieneirotdodehfofdfa weakly witiiththd1drrwarawiwtihniingaggwgrroreouaukppls3ysssdusuocchcnhaatasisns–g–CF–FC33(3H(2(2d3d–g–eere)o))aualpsllsosogigngaavvmveeatanan(e2exxfxc)ceceoelllrellenpntattrccaocon(n2vvgee)errsrspisoiionsniotoiofoff1n1.s..TrTrerarsanunsls-st-be-bodorryirynylallathtitoiieonndooeofsffired w11iwtwhidtihtrhaawawinwegeaagkkrlyolyudpdosonnsauatitcnihngga–s–C–CHCHF3 3g(gr2ordou–upeps)sainlisnommgeteaatvae(2(a2fn)f)oeorxrcpepalarlearan(t2(2cggo))npvpoeosrsistiitoionnsosfrer1es.suTultrletaedndsi-nibnotrhtyheleadtdieoesnsirieroedfd 1 1 w w i t i t h h a a w w e e a a k k l yl y d d o o n n a a t t i ni n g g – – C C H H 3 3 g g r r o o u u p p s s i ni n m m e e t t a a ( ( 2 2 f f ) ) o o r r p p a a r r a a ( ( 2 2 g g ) ) p p o o s s i t i t i oi o n n s s r r e e s s u u l t l t e e d d i ni n t t h h e e d d e e s s i r i r e e d d 11wwitihthaawweaekalkylydodnoantaitnigng–C–CHH3 3grgoruopuspsininmmeteata(2(f2)f)ororpaprara(2(g2)g)popsoistitoinosnsrerseuslutletdedininthtehededseisrierded p1prp1rwowrwdwodiitdutihtucuchtcasastas3w3wf3w3efaeanakakndndklklydyl3y3ydg3ddogowononwniaiataihtititnhnivngevegre–e–yrCr–CyCgHgHogHgHo33o3gdodoggrgdroirosouoiuosuplopolapslstasitoionininonmnmymeiyieetetialaltedal((ds2(sf2(f)Tf)()Taoaobaoraorlblrepeplapepea4rar,4a4rae,ea(n(e2(ntntg2grtg)gy)r)yp6p6po–6ooso7–si)s)7i7t.t.i)itoH.HoionoHnonswowsrwrerevsvesuevsvseuurlrelt,trlret,tdehdhtdheheiinenuiuinutitihtlhltihezlezieazdtadieietoseisnonisirnieoreodedfofodf dp1rpo1owrndowaiudtptihcutirhntcosagtdas3wu–f3wcCefateansaHakdn3kldyfl3ygag3dnrgdowodonwuina3tphiatgtitshnviwngievngiret–yhrm–CygCvHeogeHto3oray3dog(dgr2giorsfoiou)soulopodaplstraisiotsipinonioanlnramyamtiyeieo(teil2aetndalgsd(y2)(s(i2fpTe)f(laT)odobasosrlbiret(plTiep4aoara,4nbare,asln(e2rt(nr42gety,g)rsye)u6pn–pl6ot7–orse)y7isd.ti)iHt6.oi–Hono7nswo)ts.whreHerveseovusdrwuel,etrlet,sthedvitredheeireundi,ntutithplthtiezhlreioaezudtdatidieotuliesniozcisrnaitoerstfedoio3dfnfaonfd3g 1pp1rworwoditdiuhtuhcctastasw3w3fefaeaakannkldy3dly3d3gdogwonwnaitaihitnhinvgvge–eryrC–yCHgHgo3o3godgrdoriosuisoupolpsalastitnoionmnmyeyiteiateladl(d2s(s2f()fT()Toaoarbbrlpelpae4ra4a,r,ae(en2(n2gtrtg)yr)yp6po6–os–7is7)ti.)to.iHonHnososwrweresevusveulertl,ret,tdehtdheineiunuthitliheilziezadatdeitoseioisnrinerodeofdf prrooduccttss33ffaannd33ggwitithhvveerryyggooodisisoolalattioionnyyieieldldss((Taabblele44,,eennttrryy66––77))..Hooweevveerr,,tthheeuttiliilzizaattioionnooff prpordoudcutcsts3f3fanadnd3g3gwwitihthvevreyrygogododisiosloaltaitoinonyiyeiledlsds(T(aTbalbele4,4e, netnrtyry6–67–)7.)H. Howoweveevre,rt,hteheutuitlizliaztaitoinonofof tphtprheheoroeodosdtdsuseuetucrecitictrcscstiacsc3lalfl3flylyflflayayhnanhihnindnidndnd3deg3e3grgewewrdwdweiidttiaiahtlahkvlvykyvelylreryglgryyrgrgogorgoguououpupdodpd–d–iCiC–sioCs(o(Colo(l(aClHtatiHito3oi)ono3n3)n(3y2y(yiyh2ieih)leld)dgldsagsasva(a(TevTe(Taeababablbleoeleweow4w,4e, ,e,renerncntotcrtnonoyrynvnyv6eve–6–re7–s7r)i7is)so.o.)in.Ho.onHnHnoowfofowf1e.1vevA.A.veveArers,sr,is,ts,mthihtmheieleiaiaulrauttirirtlleierilzszseieazuastaulutlititoloitwononwnaosafofsf thptperhoresodtsdetuthrueciertcsitascslt3ale3fylrlfyiahcanaihndlildny3ed3ghregeirwndewdidtaiehtlarhkelvykdvelyeraglyrlrgykogryguolopougodp–rdoCi–suiC(osCpo(laCHl–atHCi3to)i(3onC)(n32yH(h2yi3e)hi)el3g)dl(dags2vsah(evT)(Teagabalblovelweoe4wea4, r,elorecnowntcrntoeyrvnyre6vcr6–eos–7rin7s)o.vi)no.HenHrosfoiwo1fwne.1evA.oveAfers,1rism,t.ihtmAihelaeisluraiutmritleirilszleiauzasrluattitrloiwteonswnauosaloftsfwas wptprihtorheoddusvtucetcrstiysc3ag3flfloayonanhddin3isdg3ogewlraweitdtihothanvlkveyreiylreyglgdrgosouod(pTdia–siboCslol(ealCat4iHto,ion3e)n3y(tyi2reihyled)ld6sg–sa(7Tv()Tae.abaHbleloeo4w4, ,enervntecrtoyr,yn6tvh–6e–7er)7s.u)i.HotiHnloiowozwfaet1vei.voeAren,r,stohitfmheteihulauetirtlsirlztiezasrtauitoclitonawnlloyaofsfhindered the sterically hindered alkyl group –C(CH3)3 (2h) gave a lower conversion of 1. A similar result was tthheesstteerricicaallylyhhinindeerreedaalklkyyllggrrooup––C((CH33))33((22h))ggaavveeaaloloweerrccoonnvveerrssioionnooff11..Assimimilialarrrreessultltwaass thtehestsetreirciaclalyllyhihnidnedreerdedalaklyklygl rgoruopup–C–C(C(CHH3)3)(32(h2)h)gagvaevea alolwowerercocnovnevresrisoinonofo1f .1A. Asismimilailrarerseuslutlwt wasas ntthnohntothetoeotietcscsietescscteaeaterebrbairiclblcieacalelalwlylwyhehehiinenindndtdtehrterheheredededaleaelalkcekltktykcyrtylyolrlgnonggrgn-n-rodro-ouodouupnonppana–taC–iCtnCi((ngngC(gCH–HO3–3))O3C3)(3(CH2H2(h2Hh3h))3)g)grgragaovravuouoveupeapal(lo2ol(iowoi2w)wie)ewrerwrcacoscsaoanosnananvpaveprpersrprlpslisioleleoidonodenndnd.o.WfoWofWfWf1e.1.eA.AaAlasliosismiomeieilxlxeieialaxrarmarmerieinsnesiusenueuldelttldtwtwhatahehesases ntonhtthoeiectsiectnsaetoberatirlbiceiclacealwallyblwhylhehineniwndtdheterehernededlteaehlalcekltckyrtoeylrlnloge-ngrcdotr-rodouonuopnanp-t–adi–CntoiCg(nC(gaCH–tHiO–n3)O3Cg3)C(3H2(–H2h3Oh)3gC)grgHaoravuo3vepuegapra(ol2o(lui2ow)piw)ewer(w2arcisaoc)sonawnvpaveaperslpsriiselaoidepon.dnpo.WlofieWf1ed1.e..AaAWlasloisesmoimeaixleliasalxaromarrmiernesxienusaduemltdltiwtnhwtaehasdes the atnhlntokheotyeitsclitscegtearearbircobilacelueallplywlwy–hhCeineni(ndCdethHrtehereded)eaelalel(kelc2kycthrytlor)lgongrgn-orda-oudovuponepna–at–CitCnil(noCg(gCwH–He3–O)3rO3)C(3cC2(Ho2hHnh3)3)vggearvarorosvueiuepoapanl(ol2(ow2iw)fie)1rew.wrcaocAasonsnvasavepimprepsrplisiolieiaonedrnd.o.rofWefW1s1.eue.AlaAtalsswlisomioamieslieaxlnxraaromrmetrisenicusneuledtaldtbwtwlhatehsaeewshenthe nnootticiceeaabblele whheenn tthhe3e e3eleleccttrroonn--doonnaattiningg ––OCH33 ggrrooup ((22ii)) waass aapplileied.. Wee aalslsoo eexxaaminineed tthhee nontoitciecaebalbelewwhehnenthteheelelcetcrtorno-nd-odnoantaitnigng–O–OCCHH3 3grgoruopup(2(i2)i)wwasasapaplpielide.d.WWeealaslosoexeaxmaminiendedthtehe rnernoaeotocaitctciectctviaeivibtatiyblbteyloefofwfwvhiviheninenynynlylctlyhyctchyhyeclceceolehohlehehelcxexetcacxaxrtnaorneneonoen-(d2-(doj2)onoj)inanitanitbnbiobnbogrorgyr–lylO–alOtaCitvCHieveH3ec3ogcuouogrgoupurpruoplpliuplnlnipngng(g2w(i2w)it)ihwthw1a1.s.1a1aA.s.sAaAfpatfepeptreplir6l6leid6ehd.h,h,.W3,3jWj3ejwewaslasaslsosobobesbsexesrarxexevmraraevemidenidnewdewidtihthtaheae rnernaoecotaitcivtrecieaieavtababyictblyteolievfowifvtwyhivnheioynenflnycvltychitcnyhelycoeleheocleleyhelxcececaltxtcorntaohrenoneen(x-2da-(jd2on)jone)inai(tatn2ibtnjnio)bngroigynr–lyaO–ObltOaoiCvtrCiHyHevHle3ac3otcgiuovgrpueorlopuciunlpoigpnu(g(pw2(li2iwi)nit)higtwhw1wa.1sasiA.tshAaftpap1feptp.replAr6ileif6dedhted.,.hr.3,W6j3Wjwehew,a3salaljsloswbosbaesxexrexavormamebvmdseinendiwnrevdwedietdhidthtawheaeith a n r e r n o e a o t a i c t c c t i e i c t v i a e v i a b t i b y l t e y l e o o w f w f v h v i h e n i n e n y n y l t c l h c y t h y e c e c l o l e o h l e e h l e c e e x t c x a r t a o n r n o n e n e - ( d - 2 ( d o 2 j o n ) j ) n a i n i a t n i t n b i n b g o g o r y r – y – O l a l O a C t i t C v H i v H e 3 e c 3 g c o o g r u o u r p o u p l u p i l n i p n g ( g 2 ( w 2 i w ) i i ) t i w h t h w a 1 a s 1 . s . A a A a p f t f p p e t e p r l i r l e 6 i d 6 e h d . h , . W, 3 W 3 j e j w e w a a a l a s s l s o s o o o b e b s x e s e x a e r a m v r v m e i e d n i d n e w d e w d i t i t h t h h t h e a a e erlreacactcrttiovivniti-tydyoofnfavvtininyyglclc–yyOcclolCohHheexxaagnnreoe(u(22pjj))(i2nini)bbwoorrayyslalattipvivpeelciceoodu.plWilnineggawlwsiotithhe1x1.a.AmAfiftnteererd66hth,,e33jrjewaacastsiovobibtsyseerorvvfeevdinwyitilthchyacalohexane reraecatcitviivtiytyofofvivniynlyclyccylcolhoehxe3axnaene(2(j2)j)ininbobroyrlyaltaitvievecocuopulpinligngwwitihth1.1A. Aftfetrer6 6h,h3, j3jwwasasobosbesrevrevdedwwitihtha a vrevereaerereaeycyarctcycytihitvihihivivgititihgyghytyhyhyoiyiofofeifvlevedvilindni(nyTy(ylyTalaclbyacylblycycelcloeo4l4loho,h,4he,exenenexeaxtnatrnrantyrnreye1((02012()j)0202j.).)j)j.).)iininbboboororyryylylaltatiitviveecocououupplliilninggwiittihth1.1. .Affttfetrerr66hh,, ,3,3j3jjwasassoobobbsbseserervrvvededdwiittihthaa vreverreayracytchvitvihiegvirthgiythyhoiyioefgilfevdhlvidny(iTnyi(eayTllcbladyclbyec(lTce4ola,oh4beh,elnexetnxar4anty,rneye1en(012t()0r2j.)yj.)i1ni0n)b.booryrylalatitviveecocouupplilninggwwitihth11. .AAftfeterr66hh, ,33j jwwaassoobbseservrveeddwwitihthaa rvevreaeracyrtcyithvihivigtiigyhtyhoyoyfiefivelvdilndin(yT(ylTcalyacbybclelcloel4oh4,he,exenxantanrtnyreye1(210(j20)).j)).ininbbooryrylalatitviveecocouupplilninggwwitihth1.1.AAftfetrer66hh, ,33j jwwasasoobbsesrevrvededwwitihthaa vveerryyhhigighhyyieieldld((Taabblele44,,eennttrryy1100)).. (v2evjr)eyriynhihbgiohgrhyiyleailetdlidv(Te(aTcbaolbeulep4,l4ie,negtnrtwyry1it01h)0.)1.. After 6 h, 3j was observed with a very high yield (Table 4, entry 10). vvereyryhhigighghyyiyeiledld(T(Tabablbele4,4e, nentrtyry101)0.). vvereyryhhigighhyyieiledld(T(Tabablele4,4e, nentrtyry101)0.). vveerryyhhigighhyyieieldld((Taabblele44, ,eennttrryy1100)). . very high yield (Table 4, entry 10). TTaTabalblele4.4B. oBoroyrlyaltaivtvievecocuopupulplpinlnligngngofo1f1f 1wwithihthaavavrairoiuosususoloelfeinfnisnsns2a2–aj–ijninRRuRu(u(uC(COO)C)Cl(HlH(H)()P)P(CPCPCy3y)232@)@2@[B[MBMMImIm][]O]O[OTfTf]fi]i]nin TaTbalbelTe4.a4Bb.olBeroy4rl.yaBltaiovtrievyeclaoctuiovpuelpicnloignugopfoli1fn1wgwiotfhit1hawaviavtrhaioraiuovsuaosrlioeolfueinfsisno2slea2f–ianj–sijn2inRa–uRj(uiCn(CORO)uC)(ClC(HlO(H))(CP)(ClP(HCy3y)(23P@)2C[@By[MB3)M2I@mI[mB][MO][OTImfT]]fi[]nOinTf] in TTaabblele44. .BBooryrylalatitviveeccoouupplilninggoof f11wwitihthaavvaariroiouussoolelefifninss22aa––j jininRRuu(C(COO)C)Cl(lH(H)()P(PCCyy3)32)@2@[B[BMImIm][]O[OTTf]f]inin Taabbllee44. .BBoorryylalattiviveeccoouupplilninggooff11witihthaavvaarrioiouussooleleffininss22aa––jjininRuu((CO))Cl(l(H))((PPCyy3)3)2@2@[[BBMIIm]][[OTTff]]inin TaTabalblele44.4.B.BoBroyrlyaltaivtiieveceocucoopuulpipnliglnignofgo1fo1wfw1ithiwthaitavhavrairoviuoasurosioloeulfesinfiosnl2seafi2–anj–sijn2inaR–uRj(uCi(nCORO)Cu)Cl(CHl(HO)(P)(CPCly(3Hy)23@)2(@[PB[CMByMImI)m][@O][[OTBfTM]fi]nIimn][OTf] in oTpoTatptpbaimtmblbiemliez4zie.e4z4zdBd.e.edBoBdrreoeryarelycatlctiaiaiototvtininoevnaeaecnoacdndunodpuelpxeitnltxrirgntargcgcaotcfioioto1fino1wncwoioctninhiotdndnhaiditatviotoavinroaisnsnro.i.isuo.susoloelfeifnisns2a2–aj–ijninRRu(uC(COO)C)Cl(lHl(H)()P(CPCy3y)32)@2@[B[BMBMI3mIm2][]O[OTTfT]fi]nin oTpoTatpibamtbliemiloze4piez.4tdeiB.mdBroeroirazyercelyatadclitaotiritvneoiveanaecnatocidnouodneupxpleaitxlnritangdrcgaotecifoxotitf1nor1awnccwoicttnioihotdnhnaidtaciviotvainorasdniro.isuot.iusosnosloe.lfeifnins s2a2–aj–jininRRuu(C(COO)C)Cl(lH(H)()P(PCCy3y)32)@2@[B[BMMImIm][]O[OTTf]f]inin TTaabblele44. .BBoorryylalatitviveeccoouupplilninggooff11witihthaavvaarrioiouussoolelefifninss22aa––jjininRRuu(C(CO)C)Cl(lH(H)()P(PCyy3)32)@2@[B[BMImIm][]O[OTTf]f]inin Toopapbtitlmiemi4zi.zeBeddoreryealacatctitovionencaoannuddpelexinxtrgtaraoctcfito1ionwnciocthonndadivtiitaoironinos.su.s olefins 2a–j in Ru(CO)Cl(H)(PCy3)2@[BMIm][OTf] in o o p p t i t mi m i z i z e e d d r r e e a a c c t i t o i o n n a a n n d d e e x x t r t r a a c c t i t o i o n n c c o o n n d d i t i i t o i o n n s s . . opotpimtimiziezdedreraecatciotinonanadndexetxrtarcatciotinoncocnodnidtiotinosn.s. opoptptiitmtmimiziizezededreraecatcitotiinonannaadnndedxetxertxarctartciatoticnotnicoocnodncodidtnitotdinoisnt.iso.ns. opoptitmimiziezdedreraecatcitoinonananddexetxrtarcatcitoinoncocnonddititoinons.s. oopptitmimizizeeddrreeaacctitoionnaannddeexxtrtraacctitoionnccoonndditiitoionnss. . optimized reaction and extraction conditions. Entry Olefin 2 Product CConovneCvreosrnisovinoenrsionExEtxrtarcEatcxitotirnoanctionIsIosloaltaIistoionolnation 3 Conversion Extraction Isolation EEnntrtyry OOlelfeifnin 22 PPrordodduuctct EnEtnrtyrEyntryOOlelfeifnOinlefin222PrPordoudPcurtcotduct33C3Conovnev[r%esri]soianoanExEtxrtarcatci[to%ino]bnbIsIosloaltaitoinonc[%c] EEnntrtyry Enttrryy EnEtnrtyry EEnntrtyry EEnntrtyry Enttrryy Olelefifnin Olleeffiin OOlelfeifnin OOlelfeifnin OOlelfeifnin 22 22 22 22 22 22 PProrodduucct t Prrooducctt PrPordoudcutct PProrododuuctct PProrodduuctct 33 CoCofofnof1nv1ev[%re[s%r]isoa]a]inoa n YEYiExeitxlerdtalrdca[t%c[it%oi]nob]b]nb YIYiseIeiosleldodlaldt[a[i%t[oi%no] nc]c] c Entry Olleeffiin Olefin 2 Prrooducctt Product 33 of 1 [%] a a Yield [%] b b Yield [%] c c 3 of 1 [%]a a Yieldd [d%]bb Yield [%]c c oof f11[%[%] ] a YYieiledld[d%[%] ]d b YYieiledld[%[%] ] c oof f11[%[%] a]aa YYiei9led49ld4d[%d[9%4] b]bbd Y Y i e i l e d l d [ %[ % ] c ] c c 11 11 1 aa aa a aa 1010100 9944ddd 8181 81 aa a 10100100 9494deed e 8181 81 aa aa aa aa aa aa 11000 9040904eded9d0 8811 aa 11000 99404d e 8811 aa 10100 990944dede 90 8181 aa 10100 9949040eee 8181 aa 10100 90 8181 11 aa aa1100090ee 8811 11 11 11 11 11 1 a a 100 9090ee 81 22 bb bb 9999 9911ddd 22 2 bb b bb b 999 99 9191deed e 777 77 777 77 22 bb bb 999 898818981eded8d8 22 b b 999 989181d 777 777 777 777 777 22 b b 999 88ee 777 22 bb bb 999 898911dede 88 22 bb bb 999 9891818eee e 22 bb bb 999 88 2 b b 99 888ee 77 33 c c c c 999 9900ddd90 33 3 ccc c cc c 9999 99 9090de ed 7878 7878 7878 33 cc cc 999 9101910eded e 33 cc cc 999 99010d 91 7788 7788 7878 7878 7878 33 cc cc 999 91ee 7788 33 cc cc 999 991900dede 91 33 c c c c 999 9909101eee e 33 cc cc 999 91 3 c c 99 9191ee 78 44 dd dd 10100 9933ddd93 d 8383 44 4 dd d dd d 10100100 9393deed 8383 83 44 dd dd 11001000 9434943eded 8833 83 44 d d 11000 99343d e e 8833 44 dd dd 10100 994933de de9494 8383 44 dd dd 10100 9939434eee 8383 44 dd dd 10100 94 8383 44 d d1100094ee 8833 4 d d 100 9494ee 83 99494eeee 55 55 5 ee ee e ee 999 ee e 999 99 9090dd 90 9900ddd d d 8181 8181 81 55 5 55 55 ee 999 ee 999 ee 999 992900dede 92e 9909202eee92 e 81 55 92 88 88 8 hh hh h hh 9393 hh h 9393 93 8181dd 81 8811ddd d e 7373 7373 73 88 88 88 88 88 88 hh h hh hh hh h hh 9933 h 9933 hh 9393 hh 9393 8181deed 787717871eded d 7733 7733 7373 7373 99 99 9 i i ii i 7474dd 74 7744ddd d e 7711 99 99 99 99 99 9 i i ii i i i i i i i ii i i 8 89 9 ii 8899 i i 8 98 9 i i i 8 98 8 9 9 i i 8 98 9 7474deed 7545754eded 77454d 7171 717171 ee ee ee ee ee 999 ee 9999 9090de ed90 9202920eded 99020d 8811 8811 8181 8181 8181 55 ee ee 999 92ee 8811 ee 5 e e 99 9292ee 81 d e ff 66 ff ff1100091ee 7799 66 66 6 f f ff f f f 10100 ff f 10100100 9393deed d 9131913eded9d3 7979 7979 79 66 66 66 66 66 ff ff fff f f f ff 11000 ff 11000 f f 1010100 f f f 1 01 1 0 0 0 0 0 ff 10100 99313d 991933dede 91 9939131eee e 7799 7799 91 91 7979 6 f f 100 91ee 79 8484dd 84 77 gg gg 9898 8844ddd 6969 77 7 gg g gg g 9898 98 8484deed 6969 69 77 gg gg 9988 8141814eded d 6699 77 gg gg 9988 88414d84 e 6699 77 gg gg 9898 881844dede 81 6969 77 gg gg 989988 8848141eee 6969 69 77 gg gg989881e6969 77 gg gg 9988 81ee 6699 g 8 h h 93 777ee 73 777eee7e7 i i 8989 ii i 898989 7 69 7373 73 77ee e 7733 ii 889989 9 i i 89 75ee 71 1010 1010 1100 1100 1010 1010 10 j j j j j j jj j j j j j j j j j j j jj j j j j j 10100 10100 100 9955ddd 9595de ed 9656965eded 99565d 996955dede 96d 9959656eee95 8787 8787 87 1 01 0 1100 1100 j j jj j j jj j j 11000 11000 10100 10100 1 01 0 0 0 8877 8787 8787 j RReaecatcitotoinoncocnodndidititotoinosns:s:[R[RuRu-u-uH-H]:1]1]:12:a2–aj–j= =0.0.10:1:1:.15.,5,11010°C°C, ,6 6h,h,h,1g1g[B[MBMMImIm][]O]O[OTfTf]f,f,9],i696n6ieneneretrtatamtmosopshphpehehrer.e. RReaecatciRotineoanctocinodnidtciotinodsn:ist:[iRo[nuRs-uH:-H[]R:1]u:12-:aH2–a]j–:1j=:2=a0–.0j.10:=1:101:.105.1,5:,1:101.50°, C°1C,10,6 6°hC,h,,16g1gh[B,[MB1MgImI[mB][MO][OTImfT],]f9[]O96,in6iTenfr9e]t6,rtaintametmrotsopasthpmehroesr.pe.here. RReeaacctitoionnccoonndditiitoionnss: :[R[Ruu-H-H]:]1:1:2:2aa––jj==00.0.011:1:1:1:1.5.5, ,11100°C°C, ,66hh, ,11gg[B[BMImIm][]O[OTTf]f,],inineertrtaatmtmoospsphheerere. . Reeaaccttiioonnccoonnddiittiioonnss::[[Ruu--H]]:1:1:2:2aa––jj==00.0.011:1:1:1:1.5.5,,11100°°C,,66hh,,11gg[B[BMIIm]][O[OTTff]],,inineerrttaatmtmoosspphheerree.. RReaecatciotinoncocnodnidtiotinosn:s:[R[uR-uH-H]:1]:12:a2–aj–j= =0.0.10:1:1:.15.,5,11010°C°C, ,6 6h,h,1g1g[B[MBMImIm][O][OTfT],f],inienretrtatamtmosopshpehrer.e. ERxExRetxaerertcartcaitocitotnoinononcncococnonondndndiditdiitittitioiitiotonoioinonsnsns:s:s:[3:R[3×R×u×-u5H-5mH]:m1L]L:1L2o:a2fo–atftj–htjeheh= e=n0-n.h0h0-.ehe1h0p:e1tptp:a1a1tn:na.a15enen.,5ea,1ta16t6010600°C°C,Co,6ro6r1h61,h06,1–0g1–8g81[08B[0bBMBabMrIramIrom]fo[]C]fOfC[COCOTOTfT2]fa,2a2]t,ain4t4i0en04re0°trC°taC,ta8m,t8momsoLps/L/hpm/ehmireneir,n,n.e,. ERxERetxraetacarctacEtictioxiotnoitnornancoctcnoinondndidticitotiinononsdsn:sist:3[:iRo[3×Run×5u-sH:5-mH3]m:L]1×:L:1o25:fa2om–atfhj–Ltejh=oen=f0-nh.t0-0heh.10pe:1tpn:a:1t1-na:h.1e5ne.,5epa,t1ta16tn0106e0°aC°tC,o6,r06o61r°h6C1h,06,–o101rg–181g10[86B0[bBM–abM1raI8morI0mfo]b[Cf]Oa[COrTO2oTf]af2f,]tCa,i4tnOi04ne20r°eatCr°tC,a48ta,0mt8m°oCmLsop,/sLm8ph/mheimnreie,Lrn.e/,.min, CCoononveverersrisoinonnof 1 EExEtxrxtatrrcatcitotoinonon YieIldsIoslolaltaIistoinonlantion Yield 33 Coonvveersrssiaoioon Exxtrtraraacctitioioonb IsIssoolalaatitioioon c 33 CConfnv1vee[r%rssi]oionn a 33 CoCofon1nv[ve%oerfsr]is1oiaoan[%n] YEiEexlxtdrtarY[ac%itceito]lidonbnb[%Y]iIesIlosdolaYl[at%iteoi]londncc[%] 33 CCoofnffnv11ve[er%[%s%ris]oa]iaonan YEYExieiexterltdaldrdac[tc%[%it%oi]o]nb]nbb YIYsiIieioeseloldldaldat[it%[%oi%on]nc]cc EYExixtertlradacct[it%oion]n bYIIsisoeolaldatit[oi%onn] c 33 of 1 [%] Yield [%] Yield [%] g 98 ooff11[[%]] Yiie9el4ld9d4[[%d%]] Yiieelld[[%]] of 1 [%] Yield [d%]94 Yield [%] hh 939933 h 9933 878171d 787811de de8177 8781717eee RERexeatacrcatitcoitoninonccoconondndidtiitioitoinonsns:s: [:R[3Ruu×-H-5H]m:]1:1L:2:2aoa–f–jtjh==e 0n0.-0.h011e:1p:1:t1:a1.5n.5,e, 1a1t10600°°C°C,, 6o6r◦hh1,6, 101g–g18[B[0BMbMaImIrmo][]fO[OCTOTf]f2,],aitnin4ee0rrt°tCaat,mtm8omosspLph/hmeerirene.,. RExetarcatciotinoncoconnddititoionns:s:[3Ru×-5Hm]:1L:2oaf–jth=e n0-.0h1e:p1t:1a.n5e, a1t1060°°C, o6r h1,601–g18[0BMbaIrmo]f[OCTOf2],atin4e0rt°Ca,tm8 omsLp/hmerine., REEexxattrcrataicocttinioonnccoconondndidtiitotiiononsns:s::33[×R×5u5m-mHL]L:1oo:f2ftaht–hejenn=--hheep0p.t0ata1nn:e1e:a1at.5t6,600°1°C1C0oorr1C166,00––611880h0b,baar1rogoffC[CBOM22aIamtt4]40[0O°°TCf,],,88minLLe/rm/mt inian,t,mosphere. ExEtxrtarcatciotinaoanacocnodnidtiotinosn:s3:3××55mmLLofotfhtbehben-nh-ehpetpatnaeneata6t060°C°Coro1r6106–01–81080babraorfoCfCOO2 a2tca4tc040°C°C,8,8mmL/Lm/mini,n, 4E54ExE5txmrmtarmrmicianticii.n.ntoi.anoanDcoDcecenotendnatredidmrtrimtitoininioioenensnde:sd3:b3×yb×y5G5mGCmLC-ML-oMSfSo.SftfSh.btehbCeCnCa-anhla-acehblucpcelulutpaltaneaetdendeedaotanot6t n06t0o°tCto°aCtloalrloarm1ma6m1mo06uo–o0n1unu–8t1ntn08to0bfoabfraeroaefogafCfegnCeOetntnOs2t.sas2 .ctat4tcA04Af0°tfefCe°tcreCeC, r8n,n8-8-nmh-mehehLpeL/Lmtptp/amtninanenein,ne, 4E54Ex5txmrtamricn4ait5c.nito.imanoaDnicnDeoc.tnoetndremdiDrtmietnoitinoendnrsem:sd3:bi3nyb×ey×5dG5mGCbmC-LyML-oMGSfo.SCft.h-tbMhebCenSCa-n.lhac-helucpeluCaptlatatenaltdceneudeaolatanot6en06dto0°ttoCoa°◦tCnlaolarotmora1tm61oa06luo–0nua1–tmn810t8o0fbouabfnrraetraoeogfoafefgCneCrOtnesOa2t.sg2a.etcancAt4t04Asft0.°efCt°reC,◦rAn8, -fn8hmt-emhrLpeL/tpnma/t-mnahinenein,ep,tane E4Ex5xtrtramaccitnitoi.onana cDcoonentdedirtimitoioinses:d:33b××y55GmCLL-MooffSt.hthbebenCn-h-ahlecepuptlatantneedaatot6n600°t°oCtaolorra11m660o0–u–11n880t0bobafarroeofafgCeOnO2t2sa.atctc440A0°f°CtCe,r,88nm-mhLeL/pm/mtainin,e, E45xtrmacitni.oncDoentderimtioinesd:3b×y55GmmCL-LMoofSft.htheenC-nah-lehcpuetlpattnaeendeatoan6t06t0°oCtaColroa1mr610o6–u01n–8t108ob0fabraeorafgoCefOnCt2sO.at4aA0tf4°tC0er,8Cnm-,h8Lepm/mtLain/nme,in,45min. 4455minin..a aDeeteterrminineeddbbyyGC--MSS..b bCaalclcuulalateteddoonntototatallaamoouunnttooffrreeaaggeenntsts..2c cAffteterrnn--hheepptatannee 4545mmini.n.a aDDetetremrminiendedbybyGGCC-M-MS.S.b bCCalacluclualtaetdedonontottoatlalamamouonutntofofreraegaegnetnst.s.c cAAfteftrern-nh-ehpetpatnaene 4a 545mmini.n. a aaDDetetremrminiendedbybyGGCC-M-MS.S. b bCCalacluclualtaetdedonontottoatlalamamouonutnctofofreraegaegnetnst.s. c ccAAftfetrern-nh-ehpetpatnaene 45D45emtmeirnimn..aianaeDdDetbeytremrGmiCni-neMdedSb.ybyCGaGClcC-uM-lMaSt.Se.bdbboCnCatlacoluctaulalltaetmdedoounonnttotftoartleaalagmaemnotuosun.nttAofoftfereraenga-eghnentpst.sa.cncceAeAfxtfettrearcnt-niho-henpe;ptcatnalcneuelatedona 4455 minin.. Deeteterrminineedd bbyy GC-M-MSS.. Caalclcuulalatetedd oonn tototatall aamoouunntt ooff rreeaaggeenntsts.. Aftfeterr nn-h-heepptatannee 45 min. Determined by GC-MS. Calculated on total amount of reagents. After n-heptane theoretical mass of the product. d n-Heptane extraction. e Supercritical CO2 extraction. 11000 100100 96 e e 96ee 99090d0eedee 919010d d d 9191d d9191 d 888d8eedee 9809808d d d 9090dd 90 d 99191d1eedee 9911d d 93913d d d 9393dd 93 9944 94 d d 9090d d 99292eeee 9922 92 d d 9393d d 9393dd 93 9933ddd 9 19 1 e 9191eee 9911d d 91d d 8484d d d 8181e e81 88181eeee 8811 81 d d 8181d d 77 777 77 d d 7474d d 775744dede 75d 7747545eee74 7711 7171 7171 7171 75 e e 7711 71 75 7575dde e 757d5eede75 975975d d 9595dd 95 d e 8877 9 6 8 78 7 8877 9696e e 87 87 7979 79 7979PDF Image | Ru-Catalyzed Repetitive Batch Borylative Coupling of Olefins
PDF Search Title:
Ru-Catalyzed Repetitive Batch Borylative Coupling of OlefinsOriginal File Name Searched:
catalysts-10-00762.pdfDIY PDF Search: Google It | Yahoo | Bing
NFT (Non Fungible Token): Buy our tech, design, development or system NFT and become part of our tech NFT network... More Info
IT XR Project Redstone NFT Available for Sale: NFT for high tech turbine design with one part 3D printed counter-rotating energy turbine. Be part of the future with this NFT. Can be bought and sold but only one design NFT exists. Royalties go to the developer (Infinity) to keep enhancing design and applications... More Info
Infinity Turbine IT XR Project Redstone Design: NFT for sale... NFT for high tech turbine design with one part 3D printed counter-rotating energy turbine. Includes all rights to this turbine design, including license for Fluid Handling Block I and II for the turbine assembly and housing. The NFT includes the blueprints (cad/cam), revenue streams, and all future development of the IT XR Project Redstone... More Info
Infinity Turbine ROT Radial Outflow Turbine 24 Design and Worldwide Rights: NFT for sale... NFT for the ROT 24 energy turbine. Be part of the future with this NFT. This design can be bought and sold but only one design NFT exists. You may manufacture the unit, or get the revenues from its sale from Infinity Turbine. Royalties go to the developer (Infinity) to keep enhancing design and applications... More Info
Infinity Supercritical CO2 10 Liter Extractor Design and Worldwide Rights: The Infinity Supercritical 10L CO2 extractor is for botanical oil extraction, which is rich in terpenes and can produce shelf ready full spectrum oil. With over 5 years of development, this industry leader mature extractor machine has been sold since 2015 and is part of many profitable businesses. The process can also be used for electrowinning, e-waste recycling, and lithium battery recycling, gold mining electronic wastes, precious metals. CO2 can also be used in a reverse fuel cell with nafion to make a gas-to-liquids fuel, such as methanol, ethanol and butanol or ethylene. Supercritical CO2 has also been used for treating nafion to make it more effective catalyst. This NFT is for the purchase of worldwide rights which includes the design. More Info
NFT (Non Fungible Token): Buy our tech, design, development or system NFT and become part of our tech NFT network... More Info
Infinity Turbine Products: Special for this month, any plans are $10,000 for complete Cad/Cam blueprints. License is for one build. Try before you buy a production license. May pay by Bitcoin or other Crypto. Products Page... More Info
CONTACT TEL: 608-238-6001 Email: greg@infinityturbine.com (Standard Web Page)