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Primary Amines by Transfer Hydrogenative Reductive Amination of Ketones by Using Cyclometalated Ir III Catalysts
Author(s) -
Talwar Dinesh,
Salguero Noemí Poyatos,
Robertson Craig M.,
Xiao Jianliang
Publication year - 2014
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.201303541
Subject(s) - reductive amination , catalysis , chemistry , transfer hydrogenation , primary (astronomy) , chemoselectivity , amination , iridium , ammonium formate , organic chemistry , formate , combinatorial chemistry , substrate (aquarium) , ruthenium , formic acid , physics , oceanography , astronomy , geology
Cyclometalated iridium complexes are found to be versatile catalysts for the direct reductive amination (DRA) of carbonyls to give primary amines under transfer‐hydrogenation conditions with ammonium formate as both the nitrogen and hydrogen source. These complexes are easy to synthesise and their ligands can be easily tuned. The activity and chemoselectivity of the catalyst towards primary amines is excellent, with a substrate to catalyst ratio (S/C) of 1000 being feasible. Both aromatic and aliphatic primary amines were obtained in high yields. Moreover, a first example of homogeneously catalysed transfer‐hydrogenative DRA has been realised for β‐keto ethers, leading to the corresponding β‐amino ethers. In addition, non‐natural α‐amino acids could also be obtained in excellent yields with this method.