Bolshan, YuriBaxter, Matthew2015-05-272022-03-292015-05-272022-03-292015-04-01https://hdl.handle.net/10155/528The synthesis of small molecules is crucial in the pharmaceutical industry for producing drugs or biologically active compounds. Specifically, the formation of new carbon-carbon bonds is of great importance in synthetic organic chemistry. Brønsted acid catalysis is a powerful synthetic tool to make many different compounds, however, the current carbon-based nucleophiles are the major limitation of acid-catalyzed reactions. In effort to expand repertoire of Brønsted acid compatible nucleophiles, we present a novel carbon-carbon bond forming methodology between acetals, ketals, and potassium phenylacetylene trifluoroborate salts. Excellent functional group tolerance is observed with this protocol including, halogen, nitrile, nitro, acid and carbonyl functionalities.enBrønstedAlkynyltrifluoroboratesAcetalsKetalsAcidThesis