Premium
Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones
Author(s) -
Polishchuk Iuliia,
Sklyaruk Jan,
Lebedev Yury,
Rueping Magnus
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005508
Subject(s) - chemistry , reductive amination , iridium , catalysis , amination , amine gas treating , rhodium , selectivity , denticity , formate , ammonia , methanol , ammonium formate , inert gas , organic chemistry , medicinal chemistry , acetonitrile , crystal structure
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 (NH 4 CO 2 H) type reaction as well as in the hydrogenative (H 2 /NH 4 AcO) 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 NH 4 CO 2 D or D 2 resulted in a high degree of deuterium incorporation into the primary amine α‐position.