Organocatalytic synthesis of (Het)biaryl scaffolds via photoinduced intra/intermolecular C(sp2)–H arylation by 2-pyridone derivatives

Tapas Kumar Das (TCGLS Member), Mrinalkanti Kundu (TCGLS Member), Biswajit Mondal (TCGLS Member), Prasanjit Ghosh and Sajal Das
Organic and Biomolecular Chemistry 2022,20, 208-218 (Published on 30th Nov 2021)

DOI: https://doi.org/10.1039/D1OB01798E

Abstract: A unique N,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)–H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcased via the construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.