Visible light-mediated Smiles rearrangements and annulations of non-activated aromatics. Issue 77 (27th August 2020)

• Record Type: Journal Article
• Authors: Lawson, Connor A.; Dominey, Andrew P.; Williams, Glynn D.; Murphy, John A.
• Is Part Of: Chemical communications. Volume 56:Issue 77(2020)
• Page Start: 11445
• Page End: 11448
• Publication Date: 2020-08-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d0cc04666c
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Novel and efficient visible light-mediated Smiles rearrangements and annulations progressing via a radical-cation intermediate catalytically generated with an acridinium salt. 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.