Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate

被引：41

作者：

Natarajan, Palani ^{[1
]}

Chaudhary, Renu

Venugopalan, Paloth

机构：

[1] Panjab Univ, Dept Chem, Chandigarh 160014, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 21期

关键词：

CORRESPONDING PARA-QUINONES; EFFICIENT SYNTHESIS; SOLVOLYTIC BEHAVIOR; ARYLBORONIC ACIDS; HIGHLY EFFICIENT; OLEFINATION; OXIDATION; (E)-NITROOLEFINS; ALKYLATION; CHEMISTRY;

D O I：

10.1021/acs.joc.5b02133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient method for the regioselective nitration of a series of aliphatic and aromatic carboxylic acids to their corresponding nitro compounds using nitronium tetrafluoroborate and silver carbonate in dimethylacetamide has been described. This transformation is believed to proceed via the alkyl-silver or aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerant of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology when compared to known methods for syntheses of nitroalkyls and nitroarenes.

引用

页码：10498 / 10504

页数：7

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