Recent discoveries of various bench-stable N-quaternized ketene N,O-acetals by our laboratory have paved the way toward novel applications in organic synthesis using these previously rare constructs. This presentation will detail the emerging reaction chemistry of these unique compounds, such as their ability to serve as “trapped ketenium ions” or participate in mild nucleophilic aromatic substitutions. Additionally, in order to spur more interest in this underexplored but valuable compound class, future directions where synthetic chemists can leverage the unusual structure and reactivity of N-quaternized ketene N,O-acetals will be described.

Bench-stable N-quaternized ketene N,O-acetals – an underexplored class of reagents for organic synthesis

ACS Spring 2022

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