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Reactivity of Arynes for Arene Dearomatization

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posted on 14.01.2019 by Rajdip Karmakar, Anh Le, Peipei Xie, Yuanzhi Xia, Daesung Lee
An 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

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Funding

We 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

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Copyright @ American Chemical Society

Citation

Karmakar, R., Le, A., Xie, P., Xia, Y., & Lee, D. (2018). Reactivity of Arynes for Arene Dearomatization. Organic Letters, 20(14), 4168-4172. doi:10.1021/acs.orglett.8b01466

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American Chemical Society

Language

en_US

issn

1523-7060

Issue date

02/07/2018

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