Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



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

Author affiliations

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.

Graphical abstract: Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics

Back to tab navigation

Supplementary files

Article information


Submitted
06 Jul 2020
Accepted
18 Aug 2020
First published
19 Aug 2020

This article is Open Access

Chem. Commun., 2020, Advance Article
Article type
Communication

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

C. A. Lawson, A. P. Dominey, G. D. Williams and J. A. Murphy, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC04666C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements