Cottrell Scholar Awards - 2016
Catalyst Design and Development to Unlock the Synthetic Potential of Olefin Hydroacylation Reactions
In the field of chemistry, the closest thing to pure magic is called a catalyst – a substance that assists in a chemical reaction without itself being consumed in that reaction.
Over the past few decades, notes Levi Stanley, assistant professor of chemistry at Iowa State University, the discovery of new catalyst systems has transformed the way organic chemists approach the synthesis of medicinally important compounds, natural products and organic materials.
“The demand for new catalysts, particularly those that lead to greener, more efficient and versatile chemical processes, remains strong,” Stanley says.
Stanley is working to identify new catalysts to address difficult problems in organic synthesis, a special branch of chemistry focused on creating organic (carbon-based) compounds via organic reactions.
Stanley’s research involves overcoming challenges associated with a specific catalytic process called olefin hydroacylation. Fundamentally, the process involves a reaction between two common functional groups in organic chemistry, an aldehyde and an alkene (also known as olefins). Catalytic olefin hydroacylation reactions couple activation of carbon-hydrogen bond in the aldehyde group with formation of a new carbon-carbon bond between the aldehyde and alkene precursors. The product of the process is a new functional group called a ketone, which is present in a wide array of important chemical architectures or serves as a building block to such compounds.
Stanley and his research associates are particularly interested in the development of the next generation of catalysts for the hydroacylation of alkenes (also known as olefins), which are molecules with at least one carbon-to-carbon double bond.
He says that while olefin hydroacylation reactions present an attractive way to construct new, potentially useful molecules, there are problems to overcome.
Not the least of which is the tendency of the catalysts of these reactions to become inactive over time. Another problem is that alkene bonds tend to be less likely to participate in the catalytic reactions if they contain more substitution than found in simple alkenes. Chemists must also control which carbon atom in the alkene carbon-carbon double bond is involved in the formation of the new carbon-carbon bond. Also, certain classes molecules produced in the hydroacylation process can be chiral or “handed” molecules in which it is necessary to control the orientation of atoms in space to obtain the desired chemical properties.
If successful, this research will open new, more earth-friendly methods to create useful chemicals and medicines.
For the education component of the Cottrell Scholar Award, Stanley plans to launch three initiatives at Iowa State: 1) establish a Freshman Research Initiative in the Chemistry Learning Community (CLC), an organization which seeks to build a community environment that fosters the educational and emotional growth of chemistry students; 2) introduce an authentic research experience into the undergraduate organic chemistry laboratory curriculum; and 3) develop new programming to improve engagement of upper-level and international students in the CLC.