Carbocations are important reactive intermediates that are invoked in many chemical transformations. These species are usually of the tricoordinated variety. Conversely, dicoordinated carbenium ions are rarely invoked as intermediates in practical chemical processes due to their high energy and energetically challenging formation.  In this talk I will discuss our recent efforts to utilize phenyl carbenium ions in C–H arylation reactions. We will describe how these high-energy dicoordinated carbocations can be generated under silylium catalysis conditions and utilized in the selective C–H arylation reactions of simple hydrocarbons.  Moreover, we will discuss our efforts to understand the mechanism of these reactions through computational insight, kinetics, and isotopic labeling studies.

Catalytic C–H insertion reactions of phenyl carbocations

255th National Meeting (2018)

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