Visible light-mediated smiles rearrangements and annulations of non-activated aromatics

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Lawson, Connor A. and Dominey, Andrew P. and Williams, Glynn D. and Murphy, John A. (2020) Visible light-mediated smiles rearrangements and annulations of non-activated aromatics. Chemical Communications, 56 (77). pp. 11445-11448. ISSN 1359-7345 (https://doi.org/10.1039/D0CC04666C)

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Abstract

We report the first examples of radical cation Smiles rearrangements. A series of aryloxy alkylamines underwent spontaneous reaction, with the amino group displacing the ipso-alkoxy group through substitution, at ambient temperature and under photoactivation by visible light in the presence of an acridinium catalyst (5 mol%). The study was extended to 3-(2-methoxyphenyl)propan-1-amine derivatives, which lack an appropriate ipso leaving group. Here, efficient cyclisations resulted in displacement of the methoxy group and formation of tetrahydroquinolines.

  • Item type:Article
    ID code:73725
    Dates:
    Date
    Event
    4 October 2020
    Published
    19 August 2020
    Published Online
    18 August 2020
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:26 Aug 2020 15:33
    Last modified:11 Nov 2024 12:48
    URI:https://strathprints.strath.ac.uk/id/eprint/73725
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