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

This is the accepted version of the following article:Hazra S., Hirano K., Miura M.. Solvent-Controlled Rhodium-Catalyzed C6-Selective C−H Alkenylation and Alkylation of 2-Pyridones with Acrylates. Asian Journal of Organic Chemistry 8, 1097 (2019), which has been published in final form at https://doi.org/10.1002/ajoc.201900190. This article may be used for non-commercialpurposes in accordance with the Wiley Self-ArchivingPolicy [https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html]
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.