Due to their stability, carbon-carbon d-bonds are inert under a vast majority of reaction conditions.  Recently, however, methods have been developed for the activation of such species through the use of transition metal catalysts.  The palladium catalyzed �-carbon elimination of triarylmethanols is an example of such a methodology (Miura et. al. J. Org. Chem., 2003,  68, 5236). The presented research describes the mechanistic investigation of this palladium-catalyzed reaction, specifically the influence of fluorinate triarylmethanols on the rate and selectivity of C-C bond activation.  Fluorine substituted triarylmethanols were chosen because of the sterically unhindered and electronically active nature of fluorine, which has been hypothesized to participate in an agostic-type interaction with the metal center to enhance intermediate stability.  Analysis of the product ratios and yields generated data to help elucidate the mechanism by which this reaction proceeds and provide additional insight into the factors that influence carbon-carbon bond activation.

Palladium-catalyzed β-carbon elimination of fluorinated triarylmethanols

243rd National Meeting (2012)

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