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

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

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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.