O-Alkylation of phenol derivatives via a nucleophilic substitution

被引:35
作者
Cazorla, Clement [1 ]
Pfordt, Emilie [1 ]
Duclos, Marie-Christine [1 ]
Metay, Estelle [1 ]
Lemaire, Marc [1 ]
机构
[1] Univ Lyon 1, Lab CAtalyse SYnth & ENvironm, ICBMS, CNRS,UMR5246, F-69622 Villeurbanne, France
关键词
COPPER-CATALYZED ARYLATION; ARYL HALIDES; PHOSPHINE-LIGANDS; CROSS-COUPLINGS; N-ARYLATION; BOND; VINYLATION; AMINATION; CHLORIDES; EFFICIENT;
D O I
10.1039/c1gc15481h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The alkylation of phenol derivatives can be achieved in good yield via Lewis or Brempty setnsted acid. The only by-product of the reaction is water and the catalyst can be recycled when using Brempty setnsted acid.
引用
收藏
页码:2482 / 2488
页数:7
相关论文
共 47 条
[1]   Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2007, 9 (04) :643-646
[2]   Electrophilic Functionalization of Non-Activated Olefins Catalyzed by Lewis Superacids [J].
Antoniotti, Sylvain ;
Poulain-Martini, Sophie ;
Dunach, Elisabet .
SYNLETT, 2010, (20) :2973-2988
[3]   Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].
Aranyos, A ;
Old, DW ;
Kiyomori, A ;
Wolfe, JP ;
Sadighi, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378
[4]   Efficient and Versatile Sol-Gel Immobilized Copper Catalyst for Ullmann Arylation of Phenols [J].
Benyahya, Sofia ;
Monnier, Florian ;
Taillefer, Marc ;
Man, Michel Wong Chi ;
Bied, Catherine ;
Ouazzani, Fouad .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) :2205-2208
[5]   Sol-gel immobilized and reusable copper-catalyst for arylation of phenols from aryl bromides [J].
Benyahya, Sofia ;
Monnier, Florian ;
Man, Michel Wong Chi ;
Bied, Catherine ;
Ouazzani, Fouad ;
Taillefer, Marc .
GREEN CHEMISTRY, 2009, 11 (08) :1121-1123
[6]   Iron-catalyzed C-O cross-couplings of phenols with aryl iodides [J].
Bistri, Olivia ;
Correa, Arkaitz ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :586-588
[7]   Research on phenol dehydration. Contribution to contact catalysis [J].
Briner, E ;
Bron-Stalet, J ;
Paillard, H .
HELVETICA CHIMICA ACTA, 1932, 15 :619-634
[8]   On the Role of Metal Contaminants in Catalyses with FeCl3 [J].
Buchwald, Stephen L. ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5586-5587
[9]   Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects [J].
Burgos, Carlos H. ;
Barder, Timothy E. ;
Huang, Xiaohua ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4321-4326
[10]   Ritter-type amidation of alkylboron derivatives with nitriles [J].
Cazorla, Clement ;
Metay, Estelle ;
Andrioletti, Bruno ;
Lemaire, Marc .
TETRAHEDRON LETTERS, 2009, 50 (49) :6855-6857