We report here a photocatalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated olefins with primary alkyl amines to selectively furnish secondary amine products. These reactions proceed through aminium radical cation (ARC) intermediates and occur at room temperature under visible light irradiation in the presence of an iridium photocatalyst and an aryl thiol hydrogen atom donor. Despite the presence of excess olefin, high selectivities are observed for secondary over tertiary amine products, even though the secondary amines are established substrates for ARC-based olefin amination under similar conditions.
We report here a photocatalytic method for the intermolecular anti-Markovnikov hydroamination of unactivated olefins with n class="Chemical">primary alkyl amines to selectively furnish secondary amine products. These reactions proceed through aminium radical cation (ARC) intermediates and occur at room temperature under visible light irradiation in the presence of an iridium photocatalyst and an aryl thiol hydrogen atom donor. Despite the presence of excess olefin, high selectivities are observed for secondary over tertiary amine products, even though the secondary amines are established substrates for ARC-based olefin amination under similar conditions.
Authors: Alice R Wong; Nicholas J Fastuca; Victor W Mak; Jeffrey K Kerkovius; Susan M Stevenson; Sarah E Reisman Journal: ACS Cent Sci Date: 2021-07-27 Impact factor: 14.553
Authors: Yangzhong Qin; Qilei Zhu; Rui Sun; Jacob M Ganley; Robert R Knowles; Daniel G Nocera Journal: J Am Chem Soc Date: 2021-06-30 Impact factor: 16.383