A copper(II)-catalyzed aza-Friedel-Crafts reaction of N-(2-pyridyl)sulfonyl aldimines:: Synthesis of unsymmetrical diaryl amines and triaryl methanes

被引:216
作者
Esquivias, J [1 ]
Arrayás, RG [1 ]
Carretero, JC [1 ]
机构
[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain
关键词
amines; copper; homogeneous catalysis; nitrogen heterocycles; Schiff bases;
D O I
10.1002/anie.200503305
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The choice of the (2-pyridyl)sulfonyl moiety as an N-protecting group and Cu(OTf)2/(±)-binap as catalyst system lead to a highly efficient aza-Friedel-Crafts reaction of electron-rich arenes (Ar2-H) and heteroarenes with N-sulfonyl imines. This protocol is also amenable to the synthesis of unsymmetrical triaryl methanes through a second electrophilic aromatic substitution with a different electron-rich arene (Ar3-H; see scheme). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:629 / 633
页数:5
相关论文
共 71 条
[1]   Triaryl methane derivatives as antiproliferative agents [J].
Al-Qawasmeh, RA ;
Lee, Y ;
Cao, MY ;
Gu, XP ;
Vassilakos, A ;
Wright, JA ;
Young, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (02) :347-350
[2]  
Aldag R, 1990, PHOTOCHROISM MOL SYS
[3]   Hydroxyalkylation of benzene derivatives by benzaldehyde in the presence of acid zeolites [J].
Alvaro, M ;
García, H ;
Sanjuán, A ;
Esplá, M .
APPLIED CATALYSIS A-GENERAL, 1998, 175 (1-2) :105-112
[4]   Copper-catalyzed anti-stereocontrolled ring-opening of azabicyclic alkenes with grignard reagents [J].
Arrayás, RG ;
Cabrera, S ;
Carretero, JC .
ORGANIC LETTERS, 2005, 7 (02) :219-221
[5]  
Baker LA, 2002, B KOR CHEM SOC, V23, P647
[6]   New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556
[7]  
Bandini M., 2004, ANGEW CHEM, V116, P560
[8]   Effect of BSA binding on photophysical and photochemical properties of triarylmethane dyes [J].
Baptista, MS ;
Indig, GL .
JOURNAL OF PHYSICAL CHEMISTRY B, 1998, 102 (23) :4678-4688
[9]   Stereoselective synthesis of optically active 2-hydroxymandelic acids and esters via Friedel-Crafts coordinated reaction:: Crystal structure of chiral dichloro[2-(1-oxido-1-menthoxy-carbonylmethyl)-4-methoxyphenoxido-O,O,O]titanium [J].
Bigi, F ;
Bocelli, G ;
Maggi, R ;
Sartori, G .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5004-5009
[10]   ASYMMETRIC ELECTROPHILIC SUBSTITUTION ON PHENOLS .1. ENANTIOSELECTIVE ORTHO-HYDROXYALKYLATION MEDIATED BY CHIRAL ALKOXYALUMINUM CHLORIDES [J].
BIGI, F ;
CASIRAGHI, G ;
CASNATI, G ;
SARTORI, G ;
FAVA, GG ;
BELICCHI, MF .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5018-5022