One-pot preparation of imines from nitroarenes by a tandem process with an Ir-Pd heterodimetallic catalyst

Chemistry : a European Journal
Alessandro ZanardiEduardo Peris

Abstract

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.

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Citations

Mar 6, 2015·The Journal of Organic Chemistry·Weixi ZhangMeiming Luo
Mar 25, 2011·The Journal of Organic Chemistry·Jing-Mei HuangWen Gong
May 20, 2015·Physical Chemistry Chemical Physics : PCCP·Huihui LiuStephan Jaenicke
Jan 30, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sifani Zavahir, Huaiyong Zhu
Jul 22, 2014·Chemistry : a European Journal·Ramananda MaityBiprajit Sarkar
Oct 10, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Niranjan DehurySrikanta Patra
Jun 20, 2013·Chemistry : a European Journal·Gregorio Guisado-BarriosEduardo Peris
Apr 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Saiwen LiuJin Zhang
May 19, 2011·Chemical Communications : Chem Comm·Chun-Chin Lee, Shiuh-Tzung Liu
Jun 5, 2013·Angewandte Chemie·Sergio GonellEduardo Peris
Jun 25, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Ielyzaveta Bratko, Montserrat Gómez
Mar 7, 2020·Organic & Biomolecular Chemistry·Bhaskar PaulSabuj Kundu
Mar 12, 2011·Chemical Reviews·Takeyuki Suzuki
Feb 6, 2017·Chemical Reviews·Eduardo Peris
Dec 17, 2020·The Journal of Organic Chemistry·Jiajun Wu, Christophe Darcel

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