偶氮基作为可离去导向基团辅助的C—H键定向硝化反应:区域专一性地合成邻苯二胺类化合物
收稿日期: 2014-10-30
修回日期: 2015-01-07
网络出版日期: 2015-01-13
基金资助
国家自然科学基金(Nos. 21172197, 21372201)、浙江工业大学"省重中之重一级学科"开放基金资助项目.
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.
张剑 , 张巍 , 任少波 , 崔建海 , 刘运奎 . 偶氮基作为可离去导向基团辅助的C—H键定向硝化反应:区域专一性地合成邻苯二胺类化合物[J]. 有机化学, 2015 , 35(3) : 647 -654 . DOI: 10.6023/cjoc201410042
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.
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