Chinese Journal of Organic Chemistry >
Orientation Nitration of C—H Bond Using Azo Group as a Removable Directing Group: Regiospecific Synthesis of o-Phenylenediamines
Received date: 2014-10-30
Revised date: 2015-01-07
Online published: 2015-01-13
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21172197, 21372201) and the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology.
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.
Zhang Jian , Zhang Wei , Ren Shaobo , Cui Jianhai , Liu Yunkui . Orientation Nitration of C—H Bond Using Azo Group as a Removable Directing Group: Regiospecific Synthesis of o-Phenylenediamines[J]. Chinese Journal of Organic Chemistry, 2015 , 35(3) : 647 -654 . DOI: 10.6023/cjoc201410042
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