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1、SupportingInformationIridium(III)-CatalyzedSequentialC(2)-ArylationandIntramolecularC–OBondFormationfromAzulenecarboxylicAcidsandDiaryliodoniumSaltsAccesstoAzulenofuranonesChanyoungMaeng,‡HyungJinSeo,‡HanealJeong,‡KyungsupLee,‡HeeChanNoh,‡andPhilHoLe
2、e†,‡,†TheKoreanAcademyofScienceandTechnology,Seongnam13630,RepublicofKorea‡DepartmentofChemistry,KangwonNationalUniversity,Chuncheon24341,RepublicofKoreaCorrespondingauthors.E-mail:phlee@kangwon.ac.kr.S1Contents1.ExperimentalSection··················
3、··································································S32.GeneralProcedure·························································································S43.StudiesontheKineticIsotopeEffect·······································
4、···························S154.X-rayCrystallography················································································S165.References································································································S196.1H
5、,13C,and19FNMRdata············································································S20S21.ExperimentalSectionGeneral:Commercialavailablereagentswereusedwithoutpurification.Azulenecarboxylicacids(1)1anddiaryliodoniumsalts(2)2werepreparedbyr
6、eportedmethod.Allreactionmixtureswerestirredmagneticallyandweremonitoredbythin-layerchromatographyusingsilicagelpre-coatedglassplates,whichwerevisualizedwithUVlightandthen,developedusingeitheriodineorasolutionofanisaldehyde.Forreactionsthatrequirehea
7、ting,oilbathwasusedasthesourceofheating.Flashcolumnchromatographywascarriedoutusingsilicagel(230-400mesh).1HNMR(400MHz),13C{1H}NMR(100MHz),and19FNMR(377MHz)spectrawererecordedonNMRspectrometer.Deuteratedchloroform,dimethylsulfoxide,andacetonewereused
8、asthesolvents,andchemicalshiftvalues(δ)arereportedinpartspermillionrelativetotheresidualsignalsofthesesolvent[δ7.26for1H(chloroform-d),δ2.50for1H(DMSO-d11316),δ2.05forH(acetoned-d6),δ77.2forC{H}(chloroform-d),δ39.5for13C{1H}(DMSO-d1316),andδ29.8,206.
