With the support of the Chemical Synthesis Program of the National Science Foundation, Professor David Sarlah is developing novel, practical reactions for the selective replacement of carbon-carbon double bonds with single bonds in six-membered rings, a process described as dearomative functionalization. Professor Sarlah is a faculty member in the Department of Chemistry at the University of Illinois, Urbana-Champaign (UIUC). The underlying theme of the work is to bridge the gap between the chemistry of carbon-carbon double bonds, an extensively studied area, and the chemistry of aromatic compounds, which have three such double bonds in a six-membered ring. Replacing the double bonds with single bonds allows for the rapid and controlled conversion of cheap, readily accessible compounds into high-value, complex molecules. This work may have broad applications in organic synthesis and medicinal chemistry. The project is conceptually interesting and has many potential applications, making it well suited for the education of scientists at all levels. Professor Sarlah is also pioneering an outreach program, Science in Action (SIA), that provides crucial hands-on science education for underrepresented students in the greater Champaign, IL area. Through the SIA program, graduate students in the department, in collaboration with local teachers, bring instructive science experiences to children in low-income schools.
Dearomatization reactions are an important class of transformations in organic synthesis. These transformations convert readily available arenes into useful synthetic intermediates with diverse applications. Whereas most modern dearomatization processes do not incorporate functionality into the aromatic framework, the proposed research aims to develop a general dearomative method that enables introduction of a wide range of functional groups. Specifically, this research describes the dearomative photocycloaddition of small molecules that enables in situ alkene-type chemistry of the resulting cycloadducts into a diverse array of partially unsaturated, functionalized products. With subsequent manipulations, this strategy permits access to a variety of substituted cyclohexadienes and di-, tri-, or tetrasubstituted cyclohexenes that are otherwise difficult to access through known methods. These classes of products are useful intermediates in the preparation of pharmaceuticals, agrochemicals, and other fine chemicals. The educational component of this project includes the development of the Science in Action program, which brings accessible science education to low-income schools in central Illinois. With the help of local teachers and other UIUC research groups, the initial model program has been expanded to reach a broader audience and extended to a wider range of science topics.
