RUI: Carbon-carbon single bond activation as a route to new organic transformations

Hope College, Holland MI

Investigators

Abstract

In this project funded by the Chemical Catalysis Program of the Chemistry Division, Professor Jeffrey B. Johnson of the Department of Chemistry at Hope College is developing new methods for the efficient production of organic compounds through the activation of carbon-carbon bonds. Carbon-carbon bonds are extremely common, making up the framework of molecules derived from living things as well as many polymers and other important materials. Despite their prevalence, there are few reaction conditions known that can selectively break these bonds. Professor Johnson and his group of undergraduate collaborators are working to understand the processes by which these few known reactions occur. They are using this information to develop new methods to activate and transform carbon-carbon bonds. Successful realization of these goals promises more efficient synthetic routes to complex molecules, including new compounds that can be examined for biological activity as potential pharmaceutical agents. Undergraduate students strengthen their personal scientific preparation through participation in this project. In turn, these undergraduates serve as Upward Bound mentors, assisting at-risk high school students prepare for college and potential futures in STEM fields. Professor Jeffrey B. Johnson is developing new reactions for the transition metal-catalyzed activation and functionalization of carbon-carbon single bonds. Undergraduate collaborators are carrying out the mechanistic investigation of the rhodium-catalyzed decarbonylation of 2-pyridylbenzophenones, determining energy barriers and identifying reaction intermediates. As Lewis basic directing groups are generally required for selective carbon-carbon bond activation, efforts focus on the use of readily removed or manipulated directing groups for the identification of conditions that allow the use of a broad range of ketones and carboxylic acid derivatives. The activation of these substrates, followed by coupling with readily available pi systems or organometallics, promises rapid access to a wide range of complex molecules with potential biological activity. 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.