Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines

David C. Miller, Jacob M. Ganley, Andrew J. Musacchio, Trevor C. Sherwood, William R. Ewing, Robert R. Knowles

Research output: Contribution to journalArticle

8 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)16590-16594
Number of pages5
JournalJournal of the American Chemical Society
Volume141
Issue number42
DOIs
StatePublished - Jan 1 2019

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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