Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones

Chemistry - A European Journal, vol. 27, pp. 5919–5922

Abstract

Abstract Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α‐position.

Authors 3

1. Jan Sklyaruk Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 Aachen Germany

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 Aachen Germany

2. Yury Lebedev corresponding

   King Abdullah University of Science and Technology

   Affiliation as printed

   KAUST Catalysis Center King Abdullah University of Science and Technology Thuwal Saudi Arabia

   KAUST Catalysis Center King Abdullah University of Science and Technology Thuwal Saudi Arabia

3. Magnus Rueping corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University · King Abdullah University of Science and Technology

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 Aachen Germany

   KAUST Catalysis Center King Abdullah University of Science and Technology Thuwal Saudi Arabia

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 Aachen Germany

   KAUST Catalysis Center King Abdullah University of Science and Technology Thuwal Saudi Arabia