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Updated: Dec 10, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics
Connor A Lawson1, Andrew P Dominey, Glynn D Williams
1Chemical Development, GSK, Gunnels Wood Road, Stevenage, SG1 2NY, UK. connor.x.lawson@gsk.com.
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.
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