Working Towards Anti-Markovnikov Hydroamination with Rhodium Pincer Complexes

Alkylamines have numerous applications, including fine chemicals and pharmaceuticals, which are annually produced on a large scale. Unfortunately, production of these chemicals results in a significant amount of waste that is detrimental to resources and the environment, and thus an alternative method is desired. Hydroamination, the direct addition of a N-H bond across a carbon-carbon double bond in the presence of a metal catalyst, offers an attractive atom-efficient route for synthesizing alkylamines.  However, two products are possible: the Markovnikov product and the elusive anti-Markovnikov product.  In our research, we are exploring the use of rhodium complexes with pincer phosphine ligands as catalysts for this reaction. The synthesis and characterization of pincer rhodium compounds and preliminary studies of their reactivity with olefins and amine will be presented.