Low catalyst loadings for copper-catalyzed O-arylation of phenols and heteroaryl halides under mild conditions was written by Yong, Fui-Fong;Teo, Yong-Chua;Yan, Yaw-Kai;Chua, Guan-Leong. And the article was included in Synlett in 2012.Synthetic Route of C11H9NO This article mentions the following:
A practical and mild strategy has been developed for the cross-coupling of O-arylation of phenol with differently substituted aryl halides and heteroaryl iodides using low catalyst loading of copper iodide under low operating temperature in DMF with TMHD as the ligand and Cs2CO3 as the base. This method tolerates a variety of functional groups including sterically hindered phenols and heteroaryl iodides to afford products in good to excellent yields (up to 95%). In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Synthetic Route of C11H9NO).
2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Synthetic Route of C11H9NO