Grant: Strategic Projects - Group

There are two key types of reactions that are involved in almost every chemical synthesis: carbon-carbon bond forming reactions, and functional group transformations. The former is essential for building up the carbon skeleton of a pharmaceutical, agrochemical, bulk or petrochemical. The latter is essential for decorating this skeleton with the chemical functionality that makes the chemical ""work"", for example, the functionality that allows a drug to interact with cells, or allows an agrochemical to work as a fertilizer. In addition, functional group manipulations are often needed to 'set-up' carbon carbon bond forming reactions such as oxidizing an alcohol to a ketone before a Grignard reaction. Oxidations and reductions are the two most common functional group interconversions. This proposal focuses on the latter transformation.Reduction is typically accomplished in one of two ways. For functional groups comprised of carbon-carbon double bonds, hydrogen and a transition metal catalyst is the best method. However, if the functional group in question is a carbon heteroatom double bond such as carbon-oxygen, then the industry standard is to employ a stoichiometric amount of an extremely reactive metal hydride reagent. For some transformations, the metal hydride is so reactive that it can over reduce the product, leading to the need to reoxidize the product to reach the desired oxidation state. This is obviously far from optimal, especially considering how frequently this reaction needs to be performed on large scale in various chemical industries. We propose to develop an alternative method for the reduction of carbon-heteroatom containing functional groups such as aldehydes, ketones, esters and amides which employs significantly less reactive reagents and a non-metal catalyst. The work will be carried out collaboratively with Queen's and Mount Allison, with BASF and Piramal as the industrial partners. Students at the two institutions will interact via weekly video conferences, and in person biannually. Interactions with industrial partners will be via at least once annual in person meetings.