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Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines.

ABSTRACT: 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.

SUBMITTER: Miller DC 

PROVIDER: S-EPMC7202396 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines.

Miller David C DC   Ganley Jacob M JM   Musacchio Andrew J AJ   Sherwood Trevor C TC   Ewing William R WR   Knowles Robert R RR  

Journal of the American Chemical Society 20191014 42

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 ove  ...[more]

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