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One‐Pot Preparation of Imines from Nitroarenes by a Tandem Process with an Ir–Pd Heterodimetallic Catalyst
Author(s) -
Zanardi Alessandro,
Mata Jose A.,
Peris Eduardo
Publication year - 2010
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.201000801
Subject(s) - aldehyde , imine , chemistry , catalysis , iridium , amine gas treating , palladium , tandem , nitro , combinatorial chemistry , alcohol , organic chemistry , ligand (biochemistry) , materials science , alkyl , biochemistry , receptor , composite material
A new tandem catalytic process has been studied for a heterodimetallic complex containing both iridium and palladium fragments connected by a 1,2,4‐trimethyltriazolyldiylidene ligand. The process implies the unprecedented preparation of imines from the direct reaction of nitroarenes and primary alcohols. The global process comprises the following steps: 1) reduction of the nitroarene to an amine, 2) oxidation of the alcohol to aldehyde, and 3) condensation of the aldehyde and the amine to form the corresponding imine. The oxidation of the alcohol to aldehyde is promoted by the iridium fragment, while the reduction of the nitro group to amine is facilitated by palladium. A wide set of different catalytic systems has been studied, showing that the Ir/Pd complex 1 is a highly active and stable catalyst in the preparation of imines.