Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Palladium-Catalyzed Directed Halogenation of Bipyridine N-Oxides

Palladium-Catalyzed Directed Halogenation of Bipyridine N-Oxides
Dieter Lentz, C. Christoph Tzschucke, Sina P. Zucker, Manuela Weber, Friedrich Wossidlo
The palladium-catalyzed directed C–H halogenation of bipyridine N-oxides was investigated. Using NCS or NBS (N-chloro- or N-bromosuccinimide) and 5 mol % Pd(OAc)2 in chlorobenzene (0.10 molar) at 110 °C, pyridine-directed functionalization took place and 3-chloro- or 3-bromobipyridine N-oxides were obtained in high yields. The reaction is sensitive to steric hindrance by 4- and 6′-substituents. Only in the latter case, where coordination of palladium by the pyridine is hindered, 3′-halogenation directed by the N-oxide function was observed. The halogenated products were deoxygenated by PCl3 or PBr3.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00444

DOI: 10.1021/acs.joc.7b00444

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