New Synthetic Methods Group

Novel Oxidation and Oxidative Functionalization Reactions

Using oxoammonium salts as reagents, we have performed a number of novel oxidation and oxidative functionalization reactions. These include the direct conversion of aldehydes to nitriles, the preparation of amides from alcohols and aldehydes, and the oxidation of diols to lactones, dialdehydes and acetals. We have also developed a range of oxidative cleavage processes. Current efforts include the development of catalytic methods for performing oxidative functionalization reactions.

Development of Cleaner, Greener Processes

Recent work has been focused on the catalyst-free esterification of biorenewable feedstocks such as levulinic acid to generate value-added commodity chemicals and the facile conversion of esters to amides.

Application of new tools for synthetic chemistry

To facilitate our methodology development work, we are interested in use of state-of-the-art equipment as tools. One example is continuous-flow processing. Highlights of our recent work include the synthesis of heterocyclic compounds in flow using supported catalysts and reagents and the preparation of the anti-cancer drug Cisplatin.

Reaction monitoring and computational chemistry

Allied to our synthetic chemistry, we use in-situ reaction monitoring and computational chemistry to explore mechanistic aspects of our work. As well as being useful for synthetic chemistry, microwave heating is, in principle, an ideal tool for performing kinetic studies. The microwave offers reproducible non-contact heating as well as precise temperature monitoring and data recording. To this end, we have used in-situ Raman and, more recently, infrared spectroscopy as tools for probing reactions from both a qualitative and quantitative standpoint. From a computational chemistry standpoint, quantum mechanical calculations are performed using Gaussian ’09 to evaluate both the kinetic and thermodynamic properties governing reactions performed in the lab. These calculations have yielded critical insight into the preferred mechanistic pathway for our reactions. With this information in hand, experiments have been tailored accordingly to allow for the efficient synthesis of target compounds. Additionally, correlations between chemical structures and properties can be assessed leading to greater insight into our current chemical research.

Education and outreach

Alongside our research work, the group is actively involved in education. We have integrated microwave-assisted chemistry into undergraduate laboratory courses as well as recently redesign the Advanced Organic Laboratory class. Outside of the laboratory, we are involved in developing new educational tools for use in the undergraduate classroom; linking key concepts with real-world applications. Dr Leadbeater has contributed a number of “Academic Minutes” on a local National Public Radio station, talking about topics as diverse as green chemistry, chirality, biofuels, why the sky is blue, and a three-part series on the chemistry behind the television show “Breaking Bad”.

Laboratory tools

Over the last few years, we have had access to an array of apparatus that allows us to perform synthetic chemistry from the mg to the kg scale. We can monitor and perform reactions at temperatures from -50°C to above 300°C. We have the capability to run reactions under an atmosphere of reactive gas such as carbon monoxide or hydrogen in either batch or flow mode. Using our Raman module, we can monitor the progress of reactions using real-time analysis.