CAREER: Expanding the Toolbox for Olefin Functionalization and Difunctionalization Reactions

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With the support of the Chemical Synthesis Program in the Division of Chemistry, Michael Young of The University of Toledo is developing new ways to install new molecular fragments at both carbon atoms of an alkene by using reaction additives to control the regiochemistry. Alkenes are common feedstock chemicals that are obtained from both petrochemical and bio-based sources. Despite the many existing strategies that have been studied for selectively converting alkene building blocks into value-added products, there are still challenges associated with the formation of product mixtures and the need for wasteful intermediate synthetical steps. Dr. Young and his research team are working to control the reactions of alkenes with simple and abundant reaction additives such as carbon dioxide. These studies have the potential to permit for more efficient syntheses of valuable chemical building blocks for new pharmaceuticals, fine chemicals, and next generation materials. Dr. Young will also introduce the practice of solvent recycling to research students and into teaching labs to emphasize the importance of sustainability. In addition, online short courses on green chemistry principles are also being developed for students and the local chemical industry workforce.Directing groups have played an essential role in advancing the field of C-H functionalization and the development of transient directing groups continues to improve the synthetic efficiency of this important strategy for achieving selective reactivity. Dr. Michael Young and his students are developing ways to use transient directing group tools for internal olefin functionalization strategies. Specifically, the regioselective arylation of free amine-tethered alkenes with aryl halides is being investigated by changing reactions conditions. This approach is designed to both improve the selectivity of internal alkene arylation reactions and facilitate product diversification. In addition, 1,2-difunctionalization reactions of activated alkenes will be studied to install C-C and C-O/C-N bonds in the same step. Mechanistic studies are planned to guide optimization and synthetic application of this new chemistry. These activities are expected to provide new approaches to the rapid diversification of amine-containing compounds, which is beneficial for developing compound libraries to support the pharmaceutical and agrochemical industries. These activities will also provide an excellent training ground in synthetic and organometallic chemistry for a diverse group of graduate, undergraduate, and high school students, as well as a postdoctoral researcher.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.