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Solvent‐Controlled Rhodium‐Catalyzed C6‐Selective C−H Alkenylation and Alkylation of 2‐Pyridones with Acrylates
Author(s) -
Hazra Sunit,
Hirano Koji,
Miura Masahiro
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900190
Subject(s) - chemistry , alkylation , rhodium , pyridine , solvent , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry
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.