The nickel catalyzed C–H oxygenation is a fundamentally impotant, but much less studied transformation. Herein, we report a nickel based catalyst that, in combination with catalytic DDQ, promotes the oxygenation of (aryl)(N-heteroaryl) methanes with molecular oxygen under neutral conditions. The strategy involves SET-induced formation of C-centered radicals giving access to (aryl)(N-heteroaryl) ketones and was extended to arylbenzyl ketones. The current approach has been successfully applied for the synthesis of an intermediate of AMG 579, an investigational drug candidate. A slightly modified catalyst system enables the synthesis of benzoxazinones directly starting from (aryl)(N-heteroaryl)methanes.

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