Organic Chemistry Portal



Tetrabutylammonium Pyridin-2-olate: A New Reagent for the Efficient Synthesis of N-Aryl Pyridin-2-ones

Huiping Zhang*, Bang-Chi Chen, Bei Wang, Sam T. Chao, Rulin Zhao, Ngiapkie Lim, Balu Balasubramanian

*Discovery Chemistry, Bristol-Myers Squibb Research and Development, Princeton, NJ 08543, USA, Email:

H. Zhang, B.-C. Chen, B. Wang, S. T. Chao, R. Zhao, N. Lim, B. Balasubramanian, Synthesis, 2008, 1523-1524.

DOI: 10.1055/s-2008-1072569


CuI-catalyzed coupling reactions of tetrabutylammonium pyridin-2-olates with aryl iodides allow an efficient synthesis of N-aryl pyridine-2-ones. This coupling reaction is mild, high-yielding, remarkably chemoselective (N- vs. O-arylation), and tolerates labile functional groups.

see article for more examples

Key Words

tetrabutylammonium pyridin-2-olate, aryl iodides, CuI-catalyzed coupling reaction, 2-pyridones, N-aryl pyridin-2-ones, N-arylation, Ullmann Coupling

ID: J66-Y2008-1290