Organometallic Chemistry of Heterocycles

University Of Rochester, Rochester NY

Investigators

Abstract

In this project funded by the Chemical Catalysis program of the Chemistry Division, Professor William Jones of the University of Rochester is examining new reactions that can be used to make organic compounds of interest in biology and the pharmaceutical industry. To accomplish this, fundamental reactions of transition metal catalysts are being examined that can be used to form heterocycles from readily available, inexpensive starting materials. Professor Jones is also examining new catalysts that can break open heterocycles and allow their structures to be altered. The broader impacts of this work include outreach to high school students to attract interest to careers in STEM related fields, as well as the development of new processes for routes to intermediates of pharmaceutical importance. The combination of a detailed physical-organometallic background combined with an understanding of how to apply modern computational methods to these problems produces extremely well trained scientists for the US chemical industry. One specific goal of this project is to examine fundamental aspects of cyclometallation via the "Concerted Metallation-Deprotonation" pathway that is now popular in organic synthetic methodology to produce heterocycles. These cyclometallation studies are revealing fundamental aspects of how these molecules effect the chemical transformations, and are providing insight into the control of the selectivity that is critical to formation of the desired product. A second goal is to develop uses for the now commonly observed transition metal based carbon-sulfur bond cleavage sulfur-containing molecules. One application involves anchoring a reversible carbon-sulfur activation catalyst to a solid support that allows this material to act as a "sulfur sponge," thereby permitting the cleanup of hydrocarbon fuels prior to combustion.