Grant: Alliance Grants

Nitrogen-containing compounds, called amines, are a critical class of molecules in agricultural, pharmaceutical, and materials industries. This is highlighted by the fact that 84% of small molecule drugs approved by the FDA contain an amine and amines are prevalent in the required building blocks of life eg. amino acids. Although ubiquitous, methods to efficiently produce amine compounds from feedstock chemicals such as alkenes have limitations. Instead multiple steps are required to convert alkenes into the valuable amine products that are required for manufacturing drugs and agrochemicals. Presently, a preferred industrial method for the synthesis of amines from alkenes relies upon first hydroformylation followed by reductive amination.Alkene substrates in hydroformylation can result in two different products; the branched and linear products. Hydroformylation can offer the linear product selectively but branched products are prepared as a mixture. For transformations targeting the branched product, costly and waste generating purification steps are required. Furthermore, industrial hydroformylation relies upon precious and expensive noble metal catalysts. Recent breakthroughs in the Schafer group at UBC for the catalytic synthesis of amines from alkenes features hydroaminoalkylation to give the branched products selectively. Hydroaminoalkylation requires N-methylated amines as substrates and these N-methylated amines can be directly prepared using CO2 to install the methyl group, as has been shown in recent breakthroughs from the Beller group. Here the Schafer and Beller groups propose to develop tandem catalytic N-CO2 methylation/hydroaminoalkylation to selectively access high-value amine fine chemicals directly from simple amines, CO2, H2 and alkenes. This strategy represents a new process for the sustainable synthesis of industrially relevant amines while directly fixing CO2 into these high value target compounds. This project will leverage world-leading technologies at both institutions and will offer team-based, international training including graduate student exchanges.