Abstract:
2-Benzyloxy-l-methylpyridinium triflate has been shown to be an effective reagent for benzylating oxygen nucleophiles under neutral conditions and mild temperatures. It has been proposed that upon heating, the title reagent decomposes to a benzyl cation followed by trapping of the reactive intermediate with an oxygen nucleophile. Specifically, it has been used to successfully benzyl ate alcohols, carboxylic acids, and phenols. The focus of this project is to extend the utility of oxypyridinium salts to include transfer of tert-butyl groups to oxygen nucleophiles. Initial studies focused on the synthesis and reactivity of 2-tert-butoxy-lmethylpyridinium triflate. Second, the reaction conditions required for the in situ generation of the key reagent and subsequent generation of tert-butyl ethers were explored.
