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Carbon Dioxide Transformation in Imidazolium Salts: Hydroaminomethylation Catalyzed by Ru‐Complexes
Author(s) -
Ali Meher,
Gual Aitor,
Ebeling Gunter,
Dupont Jairton
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201600385
Subject(s) - chemistry , hydroformylation , alkene , catalysis , ionic liquid , amination , amine gas treating , organic chemistry , medicinal chemistry , reductive amination , rhodium
Abstract The catalytic species generated by dissolving Ru 3 (CO) 12 in the ionic liquids 1‐ n ‐butyl‐3‐methyl‐imidazolium chloride or 1‐ n ‐butyl‐2,3‐dimethyl‐imidazolium chloride are efficient multifunctional catalysts for: (a) reverse water–gas shift, (b) hydroformylation of alkenes, and (c) reductive amination of aldehydes. Thus the reaction of alkenes with primary or secondary amines (alkene/amine, 1:1) under CO 2 /H 2 (1:1) affords the hydroaminomethylations products in high alkene conversions (up to 99 %) and selectivities (up to 96 %). The reaction proceeds under relatively mild reaction conditions (120 °C, 60 bar=6 MPa) and affords selectively secondary and tertiary amines. The presence of amine strongly reduces the alkene hydrogenation competitive pathway usually observed in the hydroformylation of terminal alkenes by Ru complexes. The catalytic system is also highly active for the reductive amination of aldehydes and ketones yielding amines in high yields (>90 %).