In 2006, 2-benzyloxy-1-methylpyridinium triflate (BnOPT) was introduced as a highly effective reagent for the mild benzylation of alcohols under nearly neutral conditions. The proposed mechanism for these transformations includes decomposition of the triflate salt to a benzyl cation upon mild warming, followed by attack of the nucleophilic oxygen species. Over the years this has become the primary method of benzyl etherification for complicated or sensitive substrates. Over the past decade, our lab has been focused on expanding the utility of these powerful reagents by allowing for the transfer of other electrophilic components, and the reaction with a variety of nucleophiles beyond alcohols. This poster will focus on the recent development of a variety of new substituted oxypyridinium salt derivatives that allow for tuning of the reactivity to be compatible with the paired nucleophilic component, allowing for the formation of a variety of new bond formations and functional group transformations. These new salts also provide new insights into the mechanism of how these electrophilic transfers occur, and the potential thresholds of reactivity for these compounds.

Recent developments on the reactivity and versatility of oxypyridinium salts as general-purpose electrophiles

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