Copper-catalyzed amidoalkylation of amines via C–C bond cleavage from cyclic oxaziridines

Abstract

Here, we report a copper-catalyzed C–C bond cleavage of cyclic oxaziridines and a C(sp³)–N coupling reaction with amines. The reaction, which proceeds under mild conditions and features simple operation and an ideal 100% atom economy, enables the synthesis of a wide variety of functionalized amides in moderate to excellent yields. Density functional theory (DFT) calculations reveal that copper initially catalyses N–O bond cleavage to generate an N-radical species, which in turn induces β-scission of the C–C bond by producing an amidoalkyl radical species. This reactive amidoalkyl radical species is subsequently trapped by amine nucleophiles, furnishing the final products after a C(sp³)–N reductive elimination process.