Friedel-Crafts alkylation is one of the oldest transformations in organic synthesis. Unfortunately, Friedel-Crafts reactions do not perform as well in more complex systems, in which benefits of this transformation are outweighed by elevated temperatures, stoichiometric Lewis acid, solvent quantities of arene, over-alkylation, and stoichiometric halide by-products. To circumvent these issues, a Zn(II)/TMSCl-catalyst system has been developed that affords hydroarylation of alkenes at room temperature with one equivalent of arene. Mechanistic studies of this reaction provide insight to the role that both Zn(II) and silane play in the catalytic cycle. Experiments designed to examine the relative importance of Zn(II) salt, silane, and water on the mechanism will be presented. The relationship between the mechanism of alkene activation, C—C bond formation, and the impact of reaction conditions in the synthesis of chiral arylated products will be described. <br/>

Mechanism of Zn(II)/TMSCl-catalyzed hydroarylation

253rd National Meeting (2017)

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