University of Illinois at Chicago
Browse
Dearomatization_re-revised 2.pdf (737.01 kB)

Reactivity of Arynes for Arene Dearomatization

Download (737.01 kB)
journal contribution
posted on 2019-01-14, 00:00 authored 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

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

History

Publisher Statement

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

Publisher

American Chemical Society

Language

  • en_US

issn

1523-7060

Issue date

2018-07-02

Usage metrics

    Categories

    No categories selected

    Keywords

    untagged

    Licence

    In Copyright

    Exports

    RefWorks
    BibTeX
    Ref. manager
    Endnote
    DataCite
    NLM
    DC