Palladium-catalyzed picolinamide-directed halogenation of ortho C–H bonds of benzylamine substrates
2014
Lu, Chengxi | Zhang, Shu-yu | He, Gang | Nack, William A. | Chen, Gong
We report a new set of methods for the halogenation of the ortho C–H bonds of N-benzyl picolinamides under palladium-catalyzed conditions. These reactions feature the use of a unique combination of K(Na)XO3 and K2S2O8 reagents, which enables the installation of iodo, bromo, and chloro groups onto the ortho position of N-benzyl picolinamides in a unified fashion. A variety of benzylamine products bearing complex halogen substitution can be quickly prepared from much simpler precursors in good yield and selectivity.
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