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

共 37 条

[31] Copper(II)/Silver(I)-Catalyzed Sequential Alkynylation and Annulation of Aliphatic Amides with Alkynyl Carboxylic Acids: Efficient Synthesis of Pyrrolidones
Zhang, Jitan
Li, Danyang
Chen, Hui
Wang, Binjie
Liu, Zhanxiang
Zhang, Yuhong
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (05) : 792 - 807
[32] STUDIES ON CO-ORDINATION COMPOUNDS OF SILVER(2) .I. MAGNETIC AND SPECTRAL PROPERTIES OF COMPLEXES WITH PYRIDINE CARBOXYLIC ACIDS
FOWLES, GWA
MATTHEWS, RW
WALTON, RA
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (05): : 1108 - &
[33] Syntheses, structures and properties of silver(I) complexes constructed from nitrogenous aromatic heterocyclic carboxylic acids and N-donor ligands
Gao, Hong-Ling
Zhang, Qin-Qin
Cheung, Chi Wai
Yi, Yong-Ling
Li, Fang-Fang
Qu, Jing
Jiang, Shu-Xin
Shi, Xue-Ying
Cui, Jian-Zhong
INORGANIC CHEMISTRY COMMUNICATIONS, 2014, 46 : 194 - 197
[34] Influence of organic carboxylic acids on self-assembly of silver(I) complexes containing 1,2-bis(4-pyridyl)ethane ligands
Wang, Chong-chen
Wang, Peng
Feng, Li-li
TRANSITION METAL CHEMISTRY, 2012, 37 (02) : 225 - 234
[35] Influence of organic carboxylic acids on self-assembly of silver(I) complexes containing 1,2-bis(4-pyridyl)ethane ligands
Chong-chen Wang
Peng Wang
Li–li Feng
Transition Metal Chemistry, 2012, 37 : 225 - 234
[36] Host-guest assembly of ligand systems for metal ion complexation. Synergistic solvent extraction of copper(II) and silver(I) by 1,4,8,11-tetrabenzyl-1,4,8,11-tetraazacyclodecane in combination with carboxylic acids
Gasperov, V
Gloe, K
Lindoy, LF
Mahinay, MS
DALTON TRANSACTIONS, 2004, (22) : 3829 - 3834
[37] Group 15 complexes with α-hydroxy carboxylic acids:: 7 -: The preparation and structure determination of sodium (+)-tartrato arsenate(III), [Na8As10(C4H2O6)8(C4H3O6)2(H2O)19]n; Silver(I) (+)-tartrato arsenate(III), [Ag9As10(C4H2O6)9(C4H3O6)(H4As2O5)(H2O)10]n and rubidium citrato antimonate(III), [Rb2Sb4(C6H5O7)2(C6H6O7)2(C6H7O7)4 (H2O)2]
Bott, RC
Smith, G
Sagatys, DS
Lynch, DE
Kennard, CHL
AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (11-12) : 917 - 924

← 1 2 3 4 →