Disubstituted Meldrum's acid: Another scaffold with SuFEx-like reactivity

Recent discoveries suggest that SuFEx reactivity may not be the exclusive privilege of sulfur and fluorine, but rather represents a more generalizable mode of chemical reactivity. Herein, we disclose that disubstituted Meldrum’s acid serves as a novel carbon-based scaffold with SuFEx-like reactivity. Phenols, alcohols, and amines are viable nucleophilic exchange partners in the presence of Barton’s base or DBU. A catalytic protocol has been developed and successfully applied to the gram-scale synthesis of isobu-tyrylated acetaminophen.