This poster highlights our recent efforts to site-selectively functionalize sila-adamantane at its 2-position. Sila-adamantane is the all-silicon analog of the ubiquitous carbon adamantane. Like carbon adamantane, sila-adamantane has high chemical stability, structural rigidity, and is strongly donating. Methods for the site-selective functionalization of the carbon adamantane at its 1- and 2-positions have broadly enabled its use as a building block in therapeutics, bioimaging agents, and material. Analogous functionalization approaches for sila-adamantane are anticipated to lead to similarly broad applications of use. While functionalization at its 1-position is straightforward, functionalization at the 2-position is a significant synthetic challenge. Two approaches to site-selective functionalization are discussed. The first approach hijacks the Lewis acid-mediated isomerization to install halide groups at the 2-position. The second approach seeks to more broadly attach nucleophilic groups at the 2-position. This work paves the way for the site-selective functionalization of sila-adamantane and its incorporation into molecules and materials.

Synthetic approaches to functionalizing sila-adamantane at its 2-position

ACS Spring 2022

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