Abstract
It is a difficult task to regiospecifically synthesize o-phenylenediamines from anilines via traditional elelectrophilic nitration process. This article described a method for the regiospecific synthesis of o-phenylenediamines from anilines. The procedure consisted of three steps, namely, the synthesis of azo compounds from anilines, the palladium-catalyzed azo group-directed ortho-orientation nitration of C—H bond, and the final reduction of the resulting o-nitro azo compounds to give o-phenylenediamines by the Zn/HCOOH system. In the process, the palladium-catalyzed azo group-assisted ortho-nitration of C—H bond is the key step for gaining the whole high regioselectivity. Keywords azo compounds; o-phenylenediamines; nitration; palladium catalysis; C—H bond activation
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