CAS: Organocatalysts: Acids and Bases

University Of Minnesota-Twin Cities, Minneapolis MN

Investigators

Abstract

In this project funded by the Chemical Structure, Dynamics & Mechanisms B Program of the Chemistry Division, Professor Steven R. Kass of the Department of Chemistry at the University of Minnesota-Twin Cities is developing a new strategy for enhancing the activity of organocatalysts. Catalysts are generally metal-containing compounds that accelerate the seed of a chemical reaction by lowering the activation barrier. Organocatalysts are quite novel because, unlike the great majority of useful metal-based catalysts, they rely only on carbon, hydrogen and a handful of other elements that are not metals. Organocatalysts are often considered more sustainable than metal-based catalysts because they do not require expensive, toxic, or precious metals. The ultimate goal of this research is to develop new and useful organocatalysts that are environmentally friendly, and to obtain a better understanding of how these species operate. This project lies at the interface of organic, physical, and analytical chemistry, and is particularly well suited for educating and training young scientists. This research will be conducted alongside an NSF-funded Research Experiences for Undergraduate site. Patents from the research will be explored along with industrial partnerships. Charge-enhanced acids, bases, and hydrogen bond catalysts will be prepared and characterized. Their catalytic abilities will be examined in a variety of organic transformations, and structural variations will be probed to increase their reactivity and selectivity. For example, what impact does covalent incorporation of the counterion or the use of a chiral counter-anion have on organic transformations? Different chiral platforms will be explored and incorporated into ferrocenium and cobaltocenium ions, in part, to obtain temporal control of the catalyst's acidity. These species have considerable practical potential, and this research will advance the state of chemical knowledge while also leading to developments that may benefit the environment, human health, and chemical industry. This research program spans from experiment to theory and from synthetic methodology to physical and analytical measurements. It serves, consequently as an excellent training ground for young scientists. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.