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A Photocatalytic Regioselective Hydroaminoalkylation of Aryl-Substituted Alkenes with Simple Amines
preprintsubmitted on 12.03.2021, 19:27 and posted on 02.04.2021, 07:55 by Natalia Larionova, Jun Miyatake Ondozabal, Emily G. Smith, Xacobe Cambeiro
A photocatalytic method for the alpha-selective hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of alpha-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the alpha-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group at the beta-position. Simple scale-up is demonstrated under continuous-flow conditions, highlighting the practicality of the method.