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.

Highlights

  • 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%)

  • Efficient cyclisations resulted in displacement of the methoxy group and formation of tetrahydroquinolines

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Summary

Introduction

We report the first examples of radical cation Smiles rearrangements. Inspired by recent developments in the Newman–Kwart rearrangement, where chemical, photochemical and electrochemical methods for single-electron oxidation enhanced reactivity, we proposed a radical cation approach to the Smiles rearrangement.[18] We show that a range of aryloxy alkylamines successfully undergo a mild and efficient photo-Smiles rearrangement using an acridinium salt as the organophotoredox catalyst (Scheme 1c).

Results
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