Friedel-Crafts alkylation of benzene with α,β-unsaturated amides

被引：19

作者：

Koltunov, KY ^{[1
]}

Walspurger, S ^{[1
]}

Sommer, J ^{[1
]}

机构：

[1] Univ Strasbourg, UMR 7513, Lab Phys Chem Hydrocarbures, F-67000 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 18期

关键词：

friedel-crafts; alkylation; superelectrophile; aluminum chloride; amide;

D O I：

10.1016/j.tetlet.2004.03.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of alpha, beta-unsaturated amides (RHC=CH2CONR'(2), R = H, Me, Ar; R'= H or Et) readily condense with benzene at room temperature in the presence of an excess of aluminum chloride to give the corresponding 3-phenylpropionamides in excellent yields. This simple, one-pot procedure proved to be efficient and very clean. The mechanism of these and related reactions is discussed and the participation of superelectrophilic dicationic intermediates is suggested. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3547 / 3549

页数：3

共 50 条

[21] POLYMERS VIA FRIEDEL-CRAFTS ALKYLATION
FRITZ, A
CHEMICAL TECHNOLOGY, 1972, 2 (11): : 687 - &
[22] FRIEDEL-CRAFTS ALKYLATION OF BITUMINOUS COALS
HODEK, W
MEYER, F
KOLLING, G
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 173 (MAR20): : 30 - 30
[23] FRIEDEL-CRAFTS ALKYLATION WITH HARD COAL
HODEK, W
MEYER, F
KOLLING, G
ERDOL & KOHLE ERDGAS PETROCHEMIE, 1978, 31 (07): : 327 - 327
[24] FRIEDEL-CRAFTS REACTION OF BUTADIENE WITH BENZENE
INUKAI, T
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (04): : 1124 - &
[25] Designing new α,β-unsaturated thioesters for the catalytic, enantioselective Friedel-Crafts alkylation of indoles
Bandini, M
Melloni, A
Tommasi, S
Umani-Ronchi, A
HELVETICA CHIMICA ACTA, 2003, 86 (11) : 3753 - 3763
[26] An Efficient Enantioselective Method for Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes
Hong, Liang
Wang, Lei
Chen, Chao
Zhang, Bangzhi
Wang, Rui
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) : 772 - 778
[27] Highly regioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles
Zou, Xuefei
Wang, Xiaoxia
Cheng, Cungui
Kong, Lichun
Mao, Hui
TETRAHEDRON LETTERS, 2006, 47 (22) : 3767 - 3771
[28] FRIEDEL-CRAFTS REACTIONS OF ALKENONES WITH BENZENE
ANSELL, MF
MAHMUD, SA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (22): : 2789 - 2795
[29] Highly efficient asymmetric organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated aldehydes
Jin, Shangbin
Li, Chenguang
Ma, Yuanhui
Kan, Yuhe
Zhang, Yong Jian
Zhang, Wanbin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (17) : 4011 - 4015
[30] Squaramide-catalysed asymmetric Friedel-Crafts alkylation of naphthol and unsaturated pyrazolones†‡
Wei, Ran
Gao, Li
Li, Gaihui
Tang, Li
Zhang, Guoshun
Zheng, Feilang
Song, Heng
Li, Qingshan
Ban, Shurong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (15) : 3370 - 3373

← 1 2 3 4 5 →