A Cobalt Catalyst Permits the Direct Hydrogenative Synthesis of 1H-Perimidines from a Dinitroarene and an Aldehyde

ChemSusChem. 2019 Jul 5;12(13):3013-3017. doi: 10.1002/cssc.201900498. Epub 2019 May 2.

Abstract

A new sustainable catalytic reaction, the synthesis of 1H- perimidines from a dinitroarene and an aldehyde in the presence of H2 , was achieved. An earth-abundant metal catalyst was developed to permit the efficient, highly chemoselective, and consecutive hydrogenation of dinitroarenes. The catalyst was reusable and easy to handle. The use of a specific Co complex and its pyrolysis at a certain temperature was crucial to achieve high activity for the complex organic transformation. Benzylic and aliphatic aldehydes could undergo the hydrogenative condensation, and many functional groups, including hydrogenation-sensitive examples such as iodo aryl, nitrile, olefin, and alkyne groups, were tolerated.

Keywords: cobalt; dinitroarenes; hydrogenation; perimidines; pyrolysis.