Copper-Mediated ortho-Nitration of Arene and Heteroarene CH Bonds Assisted by an 8-Aminoquinoline Directing Group

A copper‐mediated, chelation‐assisted ortho CH bond nitration of benzoic acid derivatives using sodium nitrite as the source of the nitro group has been achieved with the aid of an 8‐aminoquinoline directing group. Selective mono‐ or dinitration can be achieved by simply changing the reaction condi...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2015-03, Vol.357 (4), p.732-738
Main Authors: Liu, Jidan, Zhuang, Shaobo, Gui, Qingwen, Chen, Xiang, Yang, Zhiyong, Tan, Ze
Format: Article
Language:English
Subjects:
arenes
Aromatic compounds
Benzoic acid
Chelating
copper
CH activation
Derivatives
Functional groups
Nitration
selectivity
Sodium nitrite
Synthesis
Tolerances
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A copper‐mediated, chelation‐assisted ortho CH bond nitration of benzoic acid derivatives using sodium nitrite as the source of the nitro group has been achieved with the aid of an 8‐aminoquinoline directing group. Selective mono‐ or dinitration can be achieved by simply changing the reaction conditions. The method shows excellent functional group tolerance and provides a novel and straightforward route for the preparation of ortho‐nitrated benzoic acids.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400947