Catalyst-Dependent Selective Hydrogenation of Nitriles: Selective Synthesis of Tertiary and Secondary Amines

Yasunari Monguchi; Masahiro Mizuno; Tomohiro Ichikawa; Yuki Fujita; Eri Murakami; Tomohiro Hattori; Tomohiro Maegawa; Yoshinari Sawama; Hironao Sajiki

doi:10.1021/acs.joc.7b01823

Catalyst-Dependent Selective Hydrogenation of Nitriles: Selective Synthesis of Tertiary and Secondary Amines

J Org Chem. 2017 Oct 20;82(20):10939-10944. doi: 10.1021/acs.joc.7b01823. Epub 2017 Oct 6.

Authors

Yasunari Monguchi¹, Masahiro Mizuno¹, Tomohiro Ichikawa¹, Yuki Fujita¹, Eri Murakami¹, Tomohiro Hattori¹, Tomohiro Maegawa¹, Yoshinari Sawama¹, Hironao Sajiki¹

Affiliation

¹ Laboratory of Organic Chemistry, Gifu Pharmaceutical University , 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.

PMID: 28933155
DOI: 10.1021/acs.joc.7b01823

Abstract

In the presence of palladium on carbon (Pd/C) as a catalyst, hydrogenation of aliphatic nitriles in cyclohexane efficiently proceeded at 25-60 °C under ordinary hydrogen gas pressure to afford the corresponding tertiary amines. However, the use of rhodium on carbon (Rh/C) led to the highly selective generation of secondary amines. Hydrogenation of aromatic nitriles and cyclohexanecarbonitrile selectively produced secondary amines in the presence of either Pd/C or Rh/C.