Arylfluorosulfates were previously reported to react with aryl silyl ethers in the presence of certain base catalysts. Here, we report a new reaction of sulfur(VI) fluorides with parent phenols which obviates the silylation step and eliminates formation of the silyl fluoride byproduct altogether. Phenols are ubiquitous in synthetic chemistry, natural products, and biological macromolecules and metabolites. Additionally, this new reaction can be used for the synthesis of high molecular weight sulfate polymers that are significantly more stable than their polucarbonate analogs. Representative applications of the reaction and mechanistic insights into this new reactivity will be described.

Reactivity of phenol in sulfur(VI) fluoride exchange chemistry

254th National Meeting (2017)

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