Palladium direct arylation and annulation for the catalyzed regiocontrolled synthesis of quinolone derivatives
Abstract
A palladium-catalyzed strategy for the one-pot synthesis of quinolone derivatives from (hetero)arylamides and functionalized 1,2-dihalobenzenes is described. The transformation likely proceeds through a Pd 1,4-migration from the amide nitrogen atom to the (hetero)aryl ring or via a direct ortho-metalation process, enabling first the ortho-arylation of the (hetero)arylamide. The key C–C bond is formed via the direct functionalization of two distinct C–H bonds, avoiding the need for a prefunctionalized amide coupling partner. Subsequent intramolecular C–N bond formation via Pd-catalyzed coupling efficiently furnishes the quinolone scaffold. The protocol exhibits broad functional group tolerance, accommodating diverse substituents on the 1,2-dihalobenzene as well as a range of (hetero)aryl amides. This methodology allows the installation of functional groups at defined positions on the (hetero)aromatic rings. Additionally, the use of an air-stable, readily accessible palladium catalyst in combination with an inexpensive base enhances the synthetic utility of the process.
Related
- Regio and Stereoselective Multicomponent Palladium-Catalyzed Carbonylative Heck-Stille arylation of allylic alcohols derivatives
- Stereoselective Palladium-Catalyzed C(sp3)-H Arylation of Furanose Carboxamides
- A Practical Palladium-Catalyzed Cysteine Arylation Platform for Late-Stage Functionalization of Peptides and Proteins
- Synthesis of 5-[3-amino-imidazo[1,2- a ]pyridin-6-yl]pyridin-2-ones and derivatives through the combination of palladium-catalyzed cross-coupling and GBB multi-component reactions
- Base-catalyzed intramolecular C–H annulation reactions of o-carboranes containing nitriles, alkynes, and alkenes
BibTeX
@article{lan2026palladium,
title = {{Palladium direct arylation and annulation for the catalyzed regiocontrolled synthesis of quinolone derivatives}},
author = {Bo Lan and Thierry Roisnel and Henri Doucet},
journal = {Organic Chemistry Frontiers},
year = {2026},
month = oct,
doi = {10.1039/d6qo00563b},
url = {https://hal.science/hal-05742141v1},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Palladium direct arylation and annulation for the catalyzed regiocontrolled synthesis of quinolone derivatives
AU - Bo Lan
AU - Thierry Roisnel
AU - Henri Doucet
PY - 2026
DA - 2026/10/06
JO - Organic Chemistry Frontiers
DO - 10.1039/d6qo00563b
UR - https://hal.science/hal-05742141v1
AB - A palladium-catalyzed strategy for the one-pot synthesis of quinolone derivatives from (hetero)arylamides and functionalized 1,2-dihalobenzenes is described. The transformation likely proceeds through a Pd 1,4-migration from the amide nitrogen atom to the (hetero)aryl ring or via a direct ortho-metalation process, enabling first the ortho-arylation of the (hetero)arylamide. The key C–C bond is formed via the direct functionalization of two distinct C–H bonds, avoiding the need for a prefunctionalized amide coupling partner. Subsequent intramolecular C–N bond formation via Pd-catalyzed coupling efficiently furnishes the quinolone scaffold. The protocol exhibits broad functional group tolerance, accommodating diverse substituents on the 1,2-dihalobenzene as well as a range of (hetero)aryl amides. This methodology allows the installation of functional groups at defined positions on the (hetero)aromatic rings. Additionally, the use of an air-stable, readily accessible palladium catalyst in combination with an inexpensive base enhances the synthetic utility of the process.
SN - 2052-4110
SN - 2052-4129
ER -