Metal-Free Synthesis of N‑(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)–C(Alkyl) Bond in Water

The TBHP/TBAI-mediated synthesis of N-(pyridine-2-yl)­amides in water from ketones and 2-aminopyridine via direct oxidative C–C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)­amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate to good yields.