Abstract
The condensation of potassium acyltrifluoroborates (KATs) and hydroxylamines occurs under ambient, aqueous conditions to form KAT nitrones in a reversible manner. The KAT nitrones exchange rapidly under aqueous acidic conditions, resulting in a dynamic covalent library that can be converted to the corresponding static amides by treatment with strong acid. Extensive studies on the conditions and kinetics show that – counterintuitively – KAT nitrone formation is accelerated by water. The overall process serves as a dynamic system operating at room temperature under aqueous conditions with the rare ability of trapping the mixture into stable secondary amides.
Supplementary materials
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Supporting Information
Description
Experimental procedures, kinetics, and characterisation data
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