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

Connor A. Lawson, Andrew P. Dominey, Glynn D. Williams, John A. Murphy

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)
4 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)11445-11448
Number of pages4
JournalChemical Communications
Volume56
Issue number77
Early online date19 Aug 2020
DOIs
Publication statusPublished - 29 Sep 2020

Keywords

  • arylated amine preparation
  • non-activated aromatics
  • photoredox catalysis

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