Copper(I)-catalyzed tandem reaction of 2-iodophenols with isothiocyanates in room temperature ionic liquids

被引:5
作者
Yao, Fang [1 ,2 ]
Hao, Wenyan [1 ]
Cai, Ming-Zhong [1 ]
机构
[1] Jiangxi Normal Univ, Dept Chem, Nanchang 330022, Peoples R China
[2] Zhejiang Univ Technol, Dept Chem & Pharmaceut Engn, West Branch, Quzhou 324000, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper(I) catalysis; 2-Iminobenzo-1,3-oxathiole; Tandem reaction; Ionic liquid; 2-Iodophenol; OXATHIOLONE FUSED CHALCONES; CANCER-CELLS LINE; ONE-POT SYNTHESIS; RECYCLABLE CATALYST; COUPLING REACTIONS; HIGHLY EFFICIENT; CARBENE COMPLEX; DOMINO-REACTION; HECK REACTION; SOLVENTS;
D O I
10.1016/j.jorganchem.2012.09.010
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A copper(I)-catalyzed tandem reaction of 2-iodophenols with isothiocyanates in hydrophobic [ bmim] [PF6] ionic liquid was described, which proceeded smoothly and generated a variety of 2-iminobenzo-1,3-oxathioles in good to excellent yields. The tandem reaction that was carried out in [ bmim][ PF6] has some obvious advantages such as reaction rate acceleration and yield increasing as compared with the reaction run in volatile solvents such as toluene. Furthermore, the CuI/1,10-phenanthroline catalytic system can be reused up to 6 times without loss of activity and efficiency. (C) 2012 Elsevier B. V. All rights reserved.
引用
收藏
页码:137 / 142
页数:6
相关论文
共 37 条
[1]  
Adams CJ, 1998, CHEM COMMUN, P2097
[2]   Arylation of α-substituted acrylates in ionic liquids catalyzed by a Pd-benzothiazole carbene complex [J].
Calò, V ;
Nacci, A ;
Lopez, L ;
Napola, A .
TETRAHEDRON LETTERS, 2001, 42 (28) :4701-4703
[3]   The Heck reaction in ionic liquids: A multiphasic catalyst system [J].
Carmichael, AJ ;
Earle, MJ ;
Holbrey, JD ;
McCormac, PB ;
Seddon, KR .
ORGANIC LETTERS, 1999, 1 (07) :997-1000
[4]   Ligandless Stille cross-coupling in ionic liquids [J].
Chiappe, C ;
Imperato, G ;
Napolitano, E ;
Pieraccini, D .
GREEN CHEMISTRY, 2004, 6 (01) :33-36
[5]   Aqueous C-S cross-coupling: synthesis of 2-iminobenzo-1,3-oxathioles via CuCl2•H2O-catalyzed tandem reaction of 2-iodophenols with isothiocyanates [J].
Ding, Qiuping ;
Liu, Xianjin ;
Cao, Banpeng ;
Zong, Zhenzhen ;
Peng, Yiyuan .
TETRAHEDRON LETTERS, 2011, 52 (16) :1964-1967
[6]   Ionic liquid (molten salt) phase organometallic catalysis [J].
Dupont, J ;
de Souza, RF ;
Suarez, PAZ .
CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691
[7]   Arene hydrogenation in a room-temperature ionic liquid using a ruthenium cluster catalyst [J].
Dyson, PJ ;
Ellis, DJ ;
Parker, DG ;
Welton, T .
CHEMICAL COMMUNICATIONS, 1999, (01) :25-26
[8]   Linear dimerisation of but-1-ene in biphasic mode using buffered chloroaluminate ionic liquid solvents [J].
Ellis, B ;
Keim, W ;
Wasserscheid, P .
CHEMICAL COMMUNICATIONS, 1999, (04) :337-338
[9]   New domino-reaction for the synthesis of N4-(5-aryl-1,3-oxathiol-2-yliden)-2-phenylquinazolin-4-amines and 4-[4-aryl-5-(2-phenylquinazolin-4-yl)-1,3-thiazol-2-yl]morpholine [J].
Fathalla, W ;
Marek, J ;
Pazdera, P .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (06) :1139-1144
[10]   Diels-Alder reactions in room-temperature ionic liquids [J].
Fischer, T ;
Sethi, A ;
Welton, T ;
Woolf, J .
TETRAHEDRON LETTERS, 1999, 40 (04) :793-796