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

A unique N , O -bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide ( L1 ) catalyzed direct C(sp 2 )-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...

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Veröffentlicht in:Organic & biomolecular chemistry 2021-12, Vol.2 (1), p.28-218
Hauptverfasser: Das, Tapas Kumar, Kundu, Mrinalkanti, Mondal, Biswajit, Ghosh, Prasanjit, Das, Sajal
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Zusammenfassung:A unique N , O -bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide ( L1 ) catalyzed direct C(sp 2 )-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. A unique N , O -bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide ( L1 ) catalyzed direct C(sp 2 )-H arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01798e