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Visible Light Mediated Aryl Migration by Homolytic C−N Cleavage of Aryl Amines
Author(s) -
Alpers Dirk,
Cole Kevin P.,
Stephenson Corey R. J.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201806659
Subject(s) - pharmacophore , aryl , homolysis , chemistry , iridium , aryl radical , cleavage (geology) , bond cleavage , visible spectrum , photochemistry , medicinal chemistry , combinatorial chemistry , stereochemistry , radical , organic chemistry , catalysis , materials science , alkyl , optoelectronics , fracture (geology) , composite material
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.