Efficient Microwave-Assisted Palladium-Catalyzed Selective N-Arylation of Anilines with 2,3-Dihalopyridines in Water
Hao-Chun Hu, Cheng-Yi Chen, Shyh-Chyun Yang
TL;DR
This paper presents a green method for forming C–N bonds using microwave-assisted palladium catalysis in water, achieving high yields for N-arylation of anilines with 2,3-dihalopyridines.
Contribution
A novel microwave-assisted palladium-catalyzed N-arylation method in water with high efficiency and regioselectivity.
Findings
The optimized catalyst system achieved up to 91% yield for aminopyridine products.
The method works with various 2,3-dihalopyridines and substituted anilines, showing good regioselectivity.
The reaction mechanism follows a Pd(0)/Pd(II) cycle involving oxidative addition and reductive elimination.
Abstract
Under aqueous conditions, transition-metal catalysis offers an attractive platform for greener C–N bond formation by reducing reliance on hazardous organic solvents. Herein, we report a microwave-assisted palladium-catalyzed selective N-arylation of anilines with 2,3-dihalopyridines in water. Systematic optimization revealed that a catalyst system comprising PdCl2(1,10-phenanthroline)2 and (±)-BINAP in the presence of K3PO4 enables efficient coupling under microwave irradiation. Under the optimized conditions (PdCl2(1,10-Phenanthroline)2, 2 mol%; (±)-BINAP, 3 mol%; K3PO4, 3.5 equiv; H2O, 2.5 mL; 150 °C; 30 min), the coupling of aniline with 2,3-dichloropyridine afforded the corresponding aminopyridine product in up to 91% isolated yield. The method was extended to various 2,3-dihalopyridines and substituted anilines, providing moderate to excellent yields with good regioselectivity.…
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Taxonomy
TopicsCatalytic C–H Functionalization Methods · Catalytic Cross-Coupling Reactions · Sulfur-Based Synthesis Techniques