The activation and functionalization of carbon-carbon single bonds presents a significant challenge due to their significant thermodynamic and kinetic stability.  Miura and coworkers have demonstrated the selective cleavage of carbon-carbon single bonds followed by functionalization through coupling with an aryl halide (Journal of Organic Chemistry, 2004, 69, 6942).  Carbon-carbon bond activation is proposed to occur via  palladium-catalyzed β-alkyl elimination of an aryl group from tertiary alcohols. 

This work presents the results of the mechanistic study of β-alkyl elimination.  The nature of the mechanism was more fully understood through kinetic studies of the palladium-catalyzed coupling of triphenylmethanol and bromobenzene.  Furthermore, a series of tertiary alcohols with various substitutions were prepared and tested for the relative rate of carbon-carbon bond activation.  Intermolecular and intramolecular competition reactions examined the relative propensity of cleavage of groups containing differing hybridization, electronic properties, and sterics.  The results of this study promise to provide additional insight into the process of carbon-carbon bond activation and facilitate the future development of more general and selective methodology.