Synthesis of pillar[n]arenes (n=5 and 6) with deep eutectic solvent choline chloride 2FeCl3

被引:35
作者
Cao, Jin [1 ]
Shang, Yuhan [1 ]
Qi, Bin [1 ]
Sun, Xuzhuo [2 ]
Zhang, Lei [1 ]
Liu, Huiwen [1 ]
Zhang, Haibo [1 ]
Zhou, Xiaohai [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
[2] Henan Univ Technol, Coll Chem & Chem Engn, Zhengzhou 450001, Peoples R China
基金
美国国家科学基金会;
关键词
HOST-GUEST PROPERTIES; HIGH-YIELD SYNTHESIS; IONIC LIQUIDS; FACILE;
D O I
10.1039/c4ra15758c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel and distinct method of preparing pillar[5]arene and pillar[6]arene with high selectivity and efficiency has been achieved by condensation of 1,4-dialkoxybenzene and paraformaldehyde with the choline chloride (ChCl)/ferric chloride (FeCl3)deep eutectic solvent in CH2Cl2 at room temperature. Under the optimal conditions, the yield of pillar[5]arene and pillar[6]arene is 35% and 53%, respectively. The reaction mechanism is investigated by room-temperature X-band Electron Spin Resonance (ESR), indicating that a free radical takes part in this cyclization reaction and acts as an intermediate. Our research is the first report about the application of DESs in supramolecular macrocyclic host synthesis.
引用
收藏
页码:9993 / 9996
页数:4
相关论文
共 23 条
[1]   Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains [J].
Abbott, AP ;
Capper, G ;
Davies, DL ;
Munro, HL ;
Rasheed, RK ;
Tambyrajah, V .
CHEMICAL COMMUNICATIONS, 2001, (19) :2010-2011
[2]   O-acetylation of cellulose and monosaccharides using a zinc based ionic liquid [J].
Abbott, AP ;
Bell, TJ ;
Handa, S ;
Stoddart, B .
GREEN CHEMISTRY, 2005, 7 (10) :705-707
[3]   Ionic liquids based upon metal halide/substituted quaternary ammonium salt mixtures [J].
Abbott, AP ;
Capper, G ;
Davies, DL ;
Rasheed, R .
INORGANIC CHEMISTRY, 2004, 43 (11) :3447-3452
[4]   Quaternary ammonium zinc- or tin-containing ionic liquids: water insensitive, recyclable catalysts for Diels-Alder reactions [J].
Abbott, AP ;
Capper, G ;
Davies, DL ;
Rasheed, RH ;
Tambyrajah, V .
GREEN CHEMISTRY, 2002, 4 (01) :24-26
[5]   A facile, moisture-insensitive method for synthesis of pillar[5]arenes-the solvent templation by halogen bonds [J].
Boinski, Tomasz ;
Szumna, Agnieszka .
TETRAHEDRON, 2012, 68 (46) :9419-9422
[6]   A Facile and Efficient Preparation of Pillararenes and a Pillarquinone [J].
Cao, Derong ;
Kou, Yuhui ;
Liang, Jianquan ;
Chen, Zhizhao ;
Wang, Lingyun ;
Meier, Herbert .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9721-9723
[7]   Pillar[5]arenes: fascinating cyclophanes with a bright future [J].
Cragg, Peter J. ;
Sharma, Kushal .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (02) :597-607
[8]   Choline chloride•2ZnCl2 ionic liquid: an efficient and reusable catalyst for the solvent free Kabachnik-Fields reaction [J].
Disale, Shamrao T. ;
Kale, Sandip R. ;
Kahandal, Sandeep S. ;
Srinivasan, Thandankorai G. ;
Jayaram, Radha V. .
TETRAHEDRON LETTERS, 2012, 53 (18) :2277-2279
[9]   DIBPillar[n]arenes (n=5, 6): Syntheses, X-ray Crystal Structures, and Complexation with n-Octyltriethyl Ammonium Hexafluorophosphate [J].
Han, Chengyou ;
Ma, Fengying ;
Zhang, Zibin ;
Xia, Binyuan ;
Yu, Yihua ;
Huang, Feihe .
ORGANIC LETTERS, 2010, 12 (19) :4360-4363
[10]   The high yielding synthesis of pillar[5]arenes under Friedel-Crafts conditions explained by dynamic covalent bond formation [J].
Holler, Michel ;
Allenbach, Nicolas ;
Sonet, Jordan ;
Nierengarten, Jean-Francois .
CHEMICAL COMMUNICATIONS, 2012, 48 (20) :2576-2578