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使用硅烷/铼氧配合物体系实现芳香族硝基化合物的高化学选择性和区域选择性还原。

Highly chemo- and regioselective reduction of aromatic nitro compounds using the system silane/oxo-rhenium complexes.

机构信息

Instituto de Tecnologia Química e Biológica, Universidade Nova de Lisboa, Oeiras, Portugal.

出版信息

J Org Chem. 2009 Sep 18;74(18):6960-4. doi: 10.1021/jo9008657.

Abstract

The reduction of aromatic nitro compounds to the corresponding amines with silanes catalyzed by high valent oxo-rhenium complexes is reported. The catalytic systems PhMe(2)SiH/ReIO(2)(PPh(3))(2) (5 mol %) and PhMe(2)SiH/ReOCl(3)(PPh(3))(2) (5 mol %) reduced efficiently a series of aromatic nitro compounds in the presence of a wide range of functional groups such as ester, halo, amide, sulfone, lactone, and benzyl. This methodology also allowed the regioselective reduction of dinitrobenzenes to the corresponding nitroanilines and the reduction of an aromatic nitro group in presence of an aliphatic nitro group.

摘要

报道了高铼价态的氧代配合物催化下用硅烷将芳香族硝基化合物还原成相应胺的反应。催化体系 PhMe(2)SiH/ReIO(2)(PPh(3))(2)(5 mol%)和 PhMe(2)SiH/ReOCl(3)(PPh(3))(2)(5 mol%)在酯、卤代、酰胺、砜、内酯和苄基等多种官能团存在下,有效地还原了一系列芳香族硝基化合物。该方法还允许对二硝基苯进行区域选择性还原得到相应的硝基苯胺,并且在存在脂肪族硝基的情况下还原芳香族硝基。

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