Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines.

Ryan A Altman, Stephen L Buchwald

Index: Org. Lett. 9 , 643, (2007)

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Abstract

With use of Cu-based catalysts, 2- and 4-hydroxypyridines were N-arylated in modest to excellent yields. In the case of 2-hydroxypyridine, the use of 4,7-dimethoxy-1,10-phenanthroline, 3, expanded the scope of previous literature reports to include the use of N-containing heteroaryl halides, and 2-substituted aryl halides. In addition, by using a copper catalyst based on 2,2,6,6-tetramethylheptane-3,5-dione, 4, the first N-arylations of 4-hydroxypyridines and O-arylations of 3-hydroxypyridines with aryl bromides and iodides have been accomplished. [reaction: see text].