Session: Undergraduate Research Posters: Organic Chemistry:

Formation of aromatic-heteroatom bonds remains a significant challenge in modern organic chemistry. Many C-X forming reactions are redox neutral and couple a nucleophile and electrophile such as the Buchwald-Hartwig Coupling and Ullman-type reactions. Another strategy is to couple two nucleophiles together in the presence of an oxidant, which is employed in reactions such as the Chan-Lam Coupling and the Fleming-Tamao Oxidation. This strategy has been utilized less than the first since it usually requires somewhat fickle reaction conditions. As such, these types of oxidations have not been studied in as much depth as couplings like the Buchwald-Hartwig Coupling. Recently, our group published a convenient synthesis of organotetrafluorosilicate salts. We report the oxidation of these salts to form new aromatic carbon-heteroatom bonds. Our efforts towards optimization of reaction conditions and the substrate scope will be discussed.

Ryan Van Hoveln

Indiana State University

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