Industrial production of highly oxidized nitrile functional groups from primary amines in simple organic molecules is generally accomplished with poor atom economy, utilizes harsh additives, and generates undesirable by-products. Recently, a few reports have been published in which organotransition metal complexes have been shown to catalyze these reactions as well as the reverse reaction: double hydrogenation of nitriles to yield primary amines. Previously, my group has shown promising results for N-H activation followed by double dehydrogenation utilizing the iridium fragment (tBuPCP)Ir (tBuPCP = {κ<sup>3</sup>-2,6-bis[(di-<i>tert</i>-butylphosphino)methyl]phenyl}) and a range of amine substrates. All of these reactions have been carried out in the presence of a sacrificial hydrogen acceptor. In addition, we have shown stoichiometric reduction of nitriles in the presence of a hydrogen source. More recent results suggest that (tBuPCP)Ir can act catalytically and that the mechanistic details vary according to the sterics and electronics of the amine or nitrile substrates.

Catalytic interconversion of primary amines and nitriles by an iridium pincer complex

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.