Steric and Electronic Effects Influencing Beta-Aryl Elimination in the PdCatalyzed Carbon-Carbon Single Bond Activation of Triarylmethanols
Dr. Jeffery Johnson
Due to their inert nature, carbon-carbon δ-bonds are typically unutilized in synthetic processes. However, metal catalysts such as palladium and rhodium have been shown to catalytically activate these bonds in limited but promising systems. One such example is the palladium-catalyzed β-arylative elimination of triarylmethanols (Miura et. al. J. Org. Chem., 2003, 68, 5236). This project involves investigation into electronic and steric factors affecting the aryl elimination in the aforementioned reaction.Product analysis of electronically disparate aryl halides and aryldiphenylmethanols has shown that the aryl halide participates in the reaction before the elimination and that it alters the electronic nature of the metal center enough to provide elimination selectivity. These data represent significant progress towards elucidation of the metal center’s electronic character for the ultimate purpose of hypothesis driven methodology development.
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