Solvent-Controlled Rhodium-Catalyzed C6-Selective C-H Alkenylation and Alkylation of 2-Pyridones with Acrylates

A solvent-controlled rhodium-catalyzed C6-selective alkenylation and alkylation of 2-pyridones with acrylates via a pyridine-directed C-H cleavage was developed. Using DMF as solvent, the C-H alkenylation with acrylates selectively occurs to deliver the corresponding C6-alkenylated 2-pyridones in good yields. On the other hand, the C6-alkylated products are predominantly formed in a more polar and protic solvent, HFIP. Thus, a single set of starting substrates can be divergently transformed to C6-functionalized 2-pyridones, which are of potent interest in medicinal and pharmaceutical chemistry.