Nickel catalysed SET-induced oxygenation of (aryl)(N-heteroaryl)methanes with molecular oxygen
Abstract
Nickel catalyzed C-H oxygenation is a fundamentally important, 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 is 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.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Catalytic Cross-Coupling Reactions
Metal-Catalyzed Oxygenation Mechanisms
Publication details
- Journal / source
- Organic & Biomolecular Chemistry
- Publisher
- Royal Society of Chemistry (RSC)
- Volume
- 24
- Issue
- 7
- Pages
- 1474–1480
- Publication date
- 1 January 2026
- Language
- EN