Visible Light Mediated Aryl Migration by Homolytic C-N Cleavage of Aryl Amines

Angewandte Chemie
Dirk AlpersCorey R J Stephenson

Abstract

The photocatalytic preparation of aminoalkylated heteroarenes from haloalkylamides via a 1,4-aryl migration from nitrogen to carbon, conceptually analogous to a radical Smiles rearrangement, is reported. This method enables the substitution of amino groups in heteroaromatic compounds with aminoalkyl motifs under mild, iridium(III)-mediated photoredox conditions. It provides rapid access to thienoazepinone, a pharmacophore present in multiple drug candidates for potential treatment of different conditions, including inflammation and psychotic disorders.

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Citations

Dec 12, 2018·Chemistry : a European Journal·David M WhalleyMichael F Greaney
Aug 24, 2019·Chemistry : a European Journal·Rehanguli RuziChengjian Zhu
Aug 29, 2020·Chemical Communications : Chem Comm·David M WhalleyMichael F Greaney
Jul 6, 2020·Angewandte Chemie·José A ForniAnastasios Polyzos
Oct 1, 2020·Chemistry : a European Journal·Marie HuynhEtienne Brachet
Aug 14, 2020·Chemical Reviews·Stefano Crespi, Maurizio Fagnoni
Jun 5, 2021·Nature Communications·Fengjuan ChenWei Zeng
Jun 17, 2020·Journal of the American Chemical Society·Jianming YanJie Wu
Sep 25, 2021·Chemical Reviews·Lisa CandishSebastian Keess

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