Intermolecular Enantioselective Amination Reactions Mediated by Visible Light and a Chiral Iron Porphyrin Complex

Hussayn Ahmed, Biki Ghosh, Stefan Breitenlechner, Malte Feßner, Christian Merten, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

Abstract

In the presence of 1 mol % of a chiral iron porphyrin catalyst, various 3-arylmethyl-substituted 2-quinolones and 2-pyridones underwent an enantioselective amination reaction (20 examples; 93–99 % ee). The substrates were used as the limiting reagents, and fluorinated aryl azides (1.5 equivalents) served as nitrene precursors. The reaction is triggered by visible light which allows a facile dediazotation at ambient temperature. The selectivity of the reaction is governed by a two-point hydrogen bond interaction between the ligand of the iron catalyst and the substrate. Hydrogen bonding directs the amination to a specific hydrogen atom within the substrate that is displaced by the nitrogen substituent either in a concerted fashion or by a rebound mechanism.

Original languageEnglish
JournalAngewandte Chemie International Edition in English
DOIs
StateAccepted/In press - 2024

Keywords

  • amination
  • C−H activation
  • enantioselectivity
  • iron
  • porphyrinoids

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