Palladium catalyzed 8-aminoimidazo[1,2-]pyridine (AIP) directed selective β-C(sp)-H arylation

Palladium catalyzed 8-aminoimidazo[1,2-]pyridine (AIP) directed selective β-C(sp)-H arylation

Palladium catalyzed arylation of the inert β-C(sp 2 )-H bond of carboxylic acid derivatives is reported herein for the first time utilizing 8-aminoimidazo[1,2- a ]pyridine (AIP) as an efficacious and new inbuilt 6,5-fused bicyclic removable directing group. This protocol is scalable, exhibits high l...

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Veröffentlicht in:Organic & biomolecular chemistry 2021-01, Vol.19 (2), p.36-364
Hauptverfasser: Mondal, Biswajit, Ghosh, Prasanjit, Kundu, MrinalKanti, Das, Tapas Kumar, Das, Sajal
Format: Artikel
Sprache:eng
Schlagworte:
Carboxylic acids
Chemistry
Chemistry, Organic
Functional groups
Hydrogen bonds
Palladium
Physical Sciences
Pyridines
Science & Technology
Selectivity
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Zusammenfassung:Palladium catalyzed arylation of the inert β-C(sp 2 )-H bond of carboxylic acid derivatives is reported herein for the first time utilizing 8-aminoimidazo[1,2- a ]pyridine (AIP) as an efficacious and new inbuilt 6,5-fused bicyclic removable directing group. This protocol is scalable, exhibits high levels of β-site selectivity and tolerates a broad spectrum of functional groups. An unprecedented palladium( ii ) catalyzed selective β-C(sp 2 )-H arylation reaction using an 8-AIP (aminoimidazo[1,2- a ]pyridine) auxiliary as a new N , N -bidentate directing group has been demonstrated.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob02134b