Herein, we report a K₂S₂O₈-mediated metal-free radical dehydrogenative cross-coupling reaction that achieves direct C(sp²)-H/C(sp³)-H radical-radical coupling between N,N-dimethyl enaminones and glycine derivatives. The reaction efficiently proceeds under oxidative conditions via a single-electron transfer (SET) mechanism, generating both enaminone radicals and α-amino radicals for subsequent coupling. This methodology enables one-step synthesis of 30 structurally diverse 2,3-dicarbonylquinoline derivatives, including 2,3-benzoylquinolines, 2,3-diester quinolines, and 2-ester-3-acylquinolines. The protocol establishes a robust foundation for future applications of such 2,3-dicarbonylquinoline compounds.

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