We are a synthetic methods group that is focused on understanding and developing new reactions to solve some of the most important challenges in chemistry today, from the asymmetric construction of sp3 stereocenters to the synthesis of complex conjugated polymers. Specifically, we are motivated to develop new reactions for the organic synthesis of bioactive molecules. While most of our investigations involve the development of new transformations that leverage the unique properties of carbanions or organometallic reagents, we are also interested in understanding the underlying principles of chain transfer polymerization reactions. Key to developing new synthetic transformations is obtaining new mechanistic insights that drive their conception. In addition to our mechanism driven methodology development, we also develop and use new NMR techniques as well as devices such as multiple injection NMR (MI-NMR) spectroscopy which allows us to monitor and control the reactivity of transient species inside the NMR probe.
Reaction Discovery & Mechanistic Studies
Access to Remote Synthetic Landscapes:
Overriding Embedded Heteroatoms
It has long been recognized that the overall shape of a molecule determines its biological function. The Thomas lab is developing synthetic methods that target the remote landscape of biologically relevant heterocycles by re-engineering organolithium reagents.
Constructive Ozonolysis: C-O Bond Formation
The Thomas lab is developing new green oxygenation reactions with ozone. By employing new flow chemistry technologies, we were able to harness ozone as a constructive tool in synthesis: by capturing primary ozonides. Current efforts are focused on exploring new oxidants.
Synthesis of Reactive Materials
The Thomas Lab designs new ways to synthesize metals in a more reactive state. For example, a new Li-metal source “Li-dendrites” was prepared and shown to be over >19 times more reactive than the current industry standard. We are currently harnessing these new materials to prepare new organometallic reagents
J. Am. Chem. Soc. 2022, 144, 16631-16637.
Design of Rapid-Injection NMR Systems
The Thomas Lab designs new rapid injection NMR systems to gain new mechanistic information about the chemical reactivity of transient intermediates. For example, detailed knowledge about organolithium aggregation states is crucial to design new reactions. In addition, we have developed a new gas-injection system to investigate the mechanisms of CO2 reactivity.