Research

Our research program is centered around a) green chemistry b) the invention of new reactions and strategies for organic synthesis, and c) target synthesis of natural products & molecules of materials science interest

Central to our research is the development of efficient and environmentally benign reactions and strategies.  The Pharmaceutical Roundtable of the American Chemical Society’s Green Chemistry Institute deemed cross-couplings that avoid haloaromatics as their top aspirational reaction.  In collaboration with Professor Mitch Smith and others, we have worked to invented such reactions.  We are currently using catalytic C–H activation/borylation, often combined with subsequent chemical events, to generate pharmaceutically relevant building blocks for organic synthesis and in materials applications.  We were honored when the U.S. Environmental Protection Agency recognized this chemistry with its Presidential Green Chemistry Challenge Award.

Among the synthetic methods currently being investigated, we are particularly interested in the metal catalyzed chemistry of organosilanes and organoboranes. A central aim of these studies is the use of such compounds in efficient and environmentally benign reactions and strategies. Wherever possible we also seek to “telescope” these plus other reactions into one-pot processes.

As we develop new synthetic schemes, the reactions are optimized and their mechanisms explored. For example, we are currently learning about stereo- and regiochemical implications of [1,4]-Wittig rearrangements and allied chemistry.

Once these new reaction sequences become enabling technology for total synthesis, we apply them in the theater of natural product synthesis and towards the construction of other pharmaceutically relevant targets. Currently, we are looking to apply catalytic borylation chemistry to the total synthesis of autolytimycin and TMC-95A. 

We have also teamed up with Chemical Engineering and Materials Science Professor Andre Lee, to apply our synthetic expertise to another remarkable class of compounds, namely silsesquioxanes. These caged structures have garnered significant attention over their ability to meet the demands of medical, aerospace and materials industries. This is due to the well-defined spatial dimensions, the presence of seven inert peripheral organic moieties to accommodate solubility and processability, and one polymerizable reactive organic group. Like our other projects, we approach the synthesis of silsesquioxane through the lens of green chemistry. An example of this can be seen in our development of the first direct synthetic route leading to asymmetrically functionalized DDSQ compounds.