SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 04: 835 - 839

DOI: https://doi.org/10.6023/cjoc201301057

研究论文

水相中[BPy][HSO4]离子液体催化二茂铁醇的类Friedel-Crafts反应

  • 盛万里 ,
  • 田福利 ,
  • 杜玉英 ,
  • 吴春雨
展开
  • a 内蒙古大学化学化工学院 呼和浩特 010021;
    b 内蒙古工业大学化工学院 呼和浩特 010051

收稿日期: 2013-01-23

  修回日期: 2013-03-06

  网络出版日期: 2013-03-14

基金资助

国家自然科学基金(No. 21265010)资助项目.

收起

Friedel-Crafts Reaction of Ferrocenyl Alcohol Catalyzed by [BPy][HSO4] in Water Phase

  • Sheng Wanli ,
  • Tian Fuli ,
  • Du Yuying ,
  • Wu Chunyu
Expand
  • a Department of Chemistry, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021;
    b Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051

Received date: 2013-01-23

  Revised date: 2013-03-06

  Online published: 2013-03-14

Supported by

Project supported by the National Natural Science Foundation of China (No. 21265010).

Fold

摘要

以水和1-丁基吡啶硫酸氢盐([BPy][HSO4])酸性离子液体二者组成单相体系, 在温和条件下将二茂铁醇分散在水相中与多种亲核试剂发生类Friedel-Crafts反应, 得到了一系列含有杂原子二茂铁衍生物, 实验培养并得到了目标产物3i的晶体, X射线分析表明化合物3i属三斜晶系, P-1空间群. 该方法产率高, 操作简便, 对环境友好, 而且该离子液体可循环使用4次产率无明显降低.

关键词： [BPy][HSO4]离子液体; Friedel-Crafts反应; 催化; 晶体结构

本文引用格式

盛万里 , 田福利 , 杜玉英 , 吴春雨 . 水相中[BPy][HSO4]离子液体催化二茂铁醇的类Friedel-Crafts反应[J]. 有机化学, 2013 , 33(04) : 835 -839 . DOI: 10.6023/cjoc201301057

Abstract

A novel, environment friendly and efficient methodology for the synthesis of a series of ferrocenyl compounds using the functionalized acid ionic liquid [BPy][HSO4] as catalyst in water under mild conditions is reported. The Friedel-Crafts reaction of ferrocenyl alcohol with nucleophiles could be carried out efficiently in an “aqueous dispersion” and the corresponding ferrocenyl compounds were obtained in good to excellent yields. Suitable crystal of 3i was obtained, and the X-ray diffraction analysis indicated that compound 3i belonged to triclinic, space group P-1. The procedure reported here has the advantages of mild reaction conditions, high yields, operational simplicity and catalyst recyclability.

Key words： [BPy][HSO4] ionic liquid; Friedel-Crafts recation; catalysis; crystal structure

参考文献

[1] (a) Jin, Z.; Huo, A.; Liu, T.; Hu, Y.; Liu, J.; Fang, J. J. Organomet. Chem. 2005, 690, 1226.
(b) Diallo, A. K.; Daran, J. C.; Varret, F.; Ruiz, J.; Astruc, D. Angew. Chem., Int. Ed. 2009, 48, 3141.
(c) Debroy, P.; Roy, S. Coord. Chem. Rev. 2007, 251, 203.
(d) Horikoshi; Ryo. Coord. Chem. Rev. 2013, 257, 621.
(e) Roux, C.; Biot, C. Future Med. Chem. 2012, 4, 783.

[2] (a) LindstrJm, U. M.; Andersson, F. Angew. Chem., Int. Ed. 2006, 45, 548.
(b) Pirrung, M. C. Chem.-Eur. J. 2006, 12, 1312.
(c) Otto, S.; Engberts, F. N. Org. Biomol. Chem. 2003, 2809.
(d) Aplander, K.; Ding, R.; LindstrJm, U. M.; Wennerberg, J.; Schultz, S. Angew. Chem., Int. Ed. 2007, 46, 4543.

[3] Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275.

[4] (a) Du, Y.; Tian, F.; Han, L.; Zhu, N. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 1011.
(b) Sheng, W.; Du, Y.; Tian, F.; Han, L.; Zhu, N. Chem. Bull. 2012, 75, 1026 (in Chinese).
(盛万里, 杜玉英, 田福利, 韩利民, 竺宁, 化学通报, 2012, 75, 1026.)

[5] (a) Shirakawa, S. J.; Kobayashi, S. Org. Lett. 2007, 9, 311.
(b) Georgy, M.; Boucard, V.; Campagne, J. M. J. Am. Chem. Soc. 2005, 127, 14180.
(c) Vicennati, P.; Cozzzi, P. G. Eur. J. Org. Chem. 2007, 2248.
(d) Prajapati, S.; Mishra, A. P.; Srivastava, A. Int. J. Pharm., Chem. Biol. Sci. 2012, 2, 52.
(e) Chen, Y.; Xie, Z. Chin. J. Org. Chem. 2012, 32, 462 (in Chinese).
(陈永诚, 解正峰, 有机化学, 2012, 32, 462.)

[6] (a) Du, Y.; Tian, F.; Zhao, W. Synth. Commun. 2006, 36, 1661.
(b) Du, Y.; Sheng, W.; Terigule.; Han, L.; Zhu, N.; Chen, Q. J. Inner Mongolia Univ. 2011, 42, 662 (in Chinese).
(杜玉英, 盛万里, 特日古乐, 韩利民, 竺宁, 陈秋月, 内蒙古大学学报(自然科学版), 2011, 42, 662.)
(c) Du, Y.; Han, L.; Li, Y.; Zhu, N.; Zhang, G. J. Inner Mongolia Univ. 2012, 43, 477 (in Chinese).
(杜玉英, 韩利民, 李永栋, 竺宁, 张桂峰, 内蒙古大学学报(自然科学版), 2012, 43, 477.)

[7] Kenneth, J.; Rinehart, J.; Ronald, J.; Curby, J.; Phillip, E. S. J. Am. Chem. Soc. 1957, 79, 3420.

[8] Jiang, R.; Chu, X.; Xu, X.; Wu, B.; Ji, S. Aust. J. Chem. 2011, 64, 1530.

[9] Cozzzi, P. G.; Zoli, L. Angew. Chem., Int. Ed. 2008, 47, 4162; Green Chem. 2007, 9, 1292.
Options
文章导航

/

〈 〉