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Iron‐Catalyzed Reductive Amination of Aldehydes in Isopropyl Alcohol/Water Media as Hydrogen Sources
Author(s) -
Petricci Elena,
Santillo Niccolò,
Castagnolo Daniele,
Cini Elena,
Taddei Maurizio
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701619
Subject(s) - chemistry , reductive amination , iminium , catalysis , imine , amination , hydrogen , organic chemistry , isopropyl alcohol , primary (astronomy) , aqueous solution , isopropyl , alcohol , physics , astronomy
Reductive amination can be carried in i ‐PrOH/H 2 O as hydrogen sources using commercially available iron carbonyl complexes. Within an aqueous alkaline environment, a hydridocarboferrate is formed and its reducing potential is exploited for hydrogenation of the imine (or iminium ion) obtained in situ from aldehydes or ketones, and primary or secondary amines in almost equimolar ratio. This completely sustainable and hydrogen‐free process proceeds at 100 °C using Fe 3 (CO) 12 as catalyst precursor under convectional heating while Fe 2 (CO) 9 gave better results when the reaction was carried out under MW dielectric heating. Both enolizable and non‐enolizable aldehydes may be successfully employed in reactions with aliphatic and aromatic amines.