A novel and efficient iron-catalyzed sp carbon-hydrogen bond functionalization of benzoxazinone derivatives has been developed. For the first time, benzoxazin-2-ones were used as substrates in an oxidative dehydrogenative coupling reaction. The experiments were performed under mild reaction conditions to construct alkyl-aryl C(sp)-C(sp) bonds. The application of this method to the gram-scale synthesis of natural product cephalandole A has been accomplished in a 3-step sequence. A plausible one electron oxidation involved mechanism is proposed.

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3-Alkylquinoxalin-2(1H)-ones are synthesized via direct alkylation of quinoxalin-2(1H)-ones at the C3 position under visible light irradiation.

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