Reductive monoalkylation of aromatic and aliphatic nitro compounds and the corresponding amines with nitriles

被引：48

作者：

Nacario, R ^{[1
]}

Kotakonda, S

Fouchard, DMD

Tillekeratne, LMV

Hudson, RA

机构：

[1] Univ Toledo, Dept Chem, Coll Arts & Sci, Toledo, OH 43606 USA

[2] Univ Toledo, Dept Med & Biol Chem, Coll Pharm, Toledo, OH 43606 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 03期

关键词：

D O I：

10.1021/ol047580f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple, selective, rapid, and efficient procedure for the synthesis of secondary amines from the reductive alkylation of either aliphatic or aromatic nitro compounds and the corresponding amines is reported. Ammonium formate is used as the hydrogen source and Pd/C as the hydrogen transfer catalyst. The reaction is carried out at room temperature. The rate differences for the preferential formation of secondary over tertiary products are due to both steric and electronic factors.

引用

页码：471 / 474

页数：4

共 50 条

[41] REDUCTION OF AROMATIC AND ALIPHATIC NITRO-COMPOUNDS BY SODIUM HYDROGEN TELLURIDE
OSUKA, A
SHIMIZU, H
SUZUKI, H
CHEMISTRY LETTERS, 1983, (09) : 1373 - 1374
[42] MICRODETERMINATION OF NITRO AND NITROSO GROUPS IN ALIPHATIC AND AROMATIC-COMPOUNDS, ESPECIALLY IN NITRO-ARGININES
HEGEDUS, J
KARACSONY, EM
MAZOR, L
MIKROCHIMICA ACTA, 1980, 1 (5-6) : 407 - 414
[43] Decomposition mechanisms of trinitroalkyl compounds: a theoretical study from aliphatic to aromatic nitro compounds
Fayet, Guillaume
Rotureau, Patricia
Minisini, Benoit
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2014, 16 (14) : 6614 - 6622
[44] REGIOSELECTIVE MONOALKYLATION OF KETONES WITH ALLYLIC NITRO-COMPOUNDS
ONO, N
HAMAMOTO, I
KAJI, A
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (06) : 1863 - 1864
[45] THE REDUCTION OF ALIPHATIC AND AROMATIC N-OXIDES TO THE CORRESPONDING AMINES WITH TITANIUM(III) CHLORIDE
SEATON, QF
LAWLEY, CW
AKERS, HA
ANALYTICAL BIOCHEMISTRY, 1984, 138 (01) : 238 - 241
[46] Reduction of aromatic and aliphatic nitro groups to anilines and amines with hypophosphites associated with Pd/C
Baron, Marc
Metay, Estelle
Lemaire, Marc
Popowycz, Florence
GREEN CHEMISTRY, 2013, 15 (04) : 1006 - 1015
[47] A convenient method for the synthesis of poly(β-hydroxyiminoalkyl)amines from aliphatic nitro compounds
Semakin, Artem N.
Sukhorukov, Alexey Yu.
Lesiv, Alexey V.
Khomutova, Yulia A.
Ioffe, Sema L.
Lyssenko, Konstantin A.
SYNTHESIS-STUTTGART, 2007, (18): : 2862 - 2866
[48] PHOTOCHEMISTRY OF AROMATIC NITRO-COMPOUNDS, .13. PHOTO-REDUCTION OF STERICALLY HINDERED NITROBENZENES IN ALIPHATIC-AMINES
DOPP, D
MULLER, D
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1979, 98 (05): : 297 - 302
[49] AROMATIC-AMINES PRODUCTION BY NITRO-COMPOUNDS CATALYTIC REDUCTION
NIKOLAEV, YT
SAKS, OI
YAKUBSON, AM
KOFSMAN, AG
KHIMICHESKAYA PROMYSHLENNOST, 1981, (10): : 625 - 628
[50] Dimethylsulfoxide as an N-Methylation Reagent for Amines and Aromatic Nitro Compounds
Atkinson, Benjamin N.
Williams, Jonathan M. J.
CHEMCATCHEM, 2014, 6 (07) : 1860 - 1862

← 1 2 3 4 5 →