Ceric Ammonium Nitrate Promoted Highly Chemo- and Regioselective ortho-Nitration of Anilines under Mild Conditions

被引：3
|
作者：
Iqbal, Zafar [1 ]
Joshi, Asha [1 ]
De Saroj, Ranjan [1 ]
机构：
[1] Natl Inst Technol, Dept Chem, Srinagar 246174, Uttarakhand, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 31期
关键词：
Aniline carbamates; Ceric ammonium nitrate; Nitrating agents; Nitration reaction; Synthetic methods; C-H NITRATION; AROMATIC SULFONAMIDES; IPSO-NITRATION; NITROARENES; CONVERSION; OXIDATION; NITRITE; AMIDES; ROUTE; ACID;
D O I：
10.1002/ejoc.202200746
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new and practical strategy for chemo- and regioselective ortho-nitration of aniline carbamates under mild and neutral conditions have been disclosed using ceric ammonium nitrate (CAN) as a cheap nitrating agent. The electrophilic reaction exhibits a simple and straightforward pathway to obtain exclusively ortho-nitration products in good to excellent yields with outstanding functional groups tolerance for both electron rich and highly electron-deficient anilines. The highlight of this protocol is the role of ceric ammonium nitrate (CAN) as a cheap nitrating agent that (Ce+4) via chelation with the directing group controls the regioselectivity of electrophilic nitration without the requirement of additional metal catalyst and external oxidant.
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页数：8
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