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dc.contributor.authorKarmakar, Rajdip
dc.contributor.authorLe, Anh
dc.contributor.authorXie, Peipei
dc.contributor.authorXia, Yuanzhi
dc.contributor.authorLee, Daesung
dc.date.accessioned2018-10-18T21:12:15Z
dc.date.available2018-10-18T21:12:15Z
dc.date.issued2018-07-02
dc.identifier.issn1523-7060
dc.identifier.other10.1021/acs.orglett.8b01466
dc.identifier.urihttp://hdl.handle.net/10027/22775
dc.descriptionCopyright @ American Chemical Societyen_US
dc.description.abstractAn unprecedented aryne-mediated dearomatization reaction is described. An aryne intermediate generated from arenesulfonyl ynamide-tethered tri- and tetraynes reacts with both the π-systems of a tethered alkene and the arenesulfonyl group to generate cyclohexa-1,3-diene-containing penta- and hexacyclic frameworks. DFT-calculations show a nucleophilic dearomatization mechanism involving a zwitterionic intermediate derived from an aryne. A novel halogen effect on the efficiency of the dearomatization and deterrence of aromatization of the cyclohexa-1,3-diene moiety was also observed.en_US
dc.description.sponsorshipWe are grateful to NSF (CHE 1361620, D.L.) and the NSFC (21372178 and 21572163, Y.X.) for financial support. The Mass Spectrometry Laboratory at UIUC is greatly acknowledged.en_US
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.titleReactivity of Arynes for Arene Dearomatizationen_US
dc.typeArticleen_US
dc.identifier.citationKarmakar, R., Le, A., Xie, P. P., Xia, Y. Z., & Lee, D. (2018). Reactivity of Arynes for Arene Dearomatization. Organic Letters, 20(14), 4168-4172. doi:10.1021/acs.orglett.8b01466en_US


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