研究简报

全氟辛基磺酸茂锆催化吲哚与羰基化合物反应

  • 易卫国 ,
  • 贾振永 ,
  • 李宁波 ,
  • 邱仁华 ,
  • 陈锦杨 ,
  • 许新华
展开
  • a 湖南化工职业技术学院 株洲 412004;
    b 湖南大学化学化工学院 长沙 410082

收稿日期: 2012-07-12

  修回日期: 2012-08-06

  网络出版日期: 2012-08-10

基金资助

国家自然科学基金(Nos. 21172061, 21273068)资助项目.

Zirconocene Bis(perfluorooctanesulfonate)s-Catalyzed the Reaction of Indoles and Carbonyl Compounds

  • Yi Weiguo ,
  • Jia Zhenyong ,
  • Li Ningbo ,
  • Qiu Renhua ,
  • Chen Jinyang ,
  • Xu Xinhua
Expand
  • a Hunan Chemical Industry Vocation Technology Institute, Zhuzhou 412004;
    b College of Chemistry Chemical Engineering, Hunan University, Changsha 410082

Received date: 2012-07-12

  Revised date: 2012-08-06

  Online published: 2012-08-10

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172061, 21273068).

摘要

在1.0 mol%二(全氟辛基磺酸)二茂锆存在下, 吲哚与醛、酮在室温、四氢呋喃中反应10~25 min, 生成二吲哚甲烷衍生物, 收率达86%~96%. 催化剂二(全氟辛基磺酸)二茂锆能重复使用6次, 转化率仍有90%; 反应不需要在严格的无水条件下进行, 上述过程为二吲哚甲烷衍生物制备提供一条新的有效途径.

本文引用格式

易卫国 , 贾振永 , 李宁波 , 邱仁华 , 陈锦杨 , 许新华 . 全氟辛基磺酸茂锆催化吲哚与羰基化合物反应[J]. 有机化学, 2012 , 32(12) : 2390 -2393 . DOI: 10.6023/cjoc201207017

Abstract

In the presence of 1.0 mol% zirconocene bis(perfluorooctanesulfonate)s, indoles reacted with aldehyde/ketone at room temperature in tetrahydrofuran for 10~25 min to give diindolylmethane derivatives in 86%~96% yields. The catalyst zirconocene bis(perfluorooctanesulfonate)s can be reused 6 times, and the conversion rate is still as high as 90%. This reaction does not require strict anhydrous conditions. This procedure provides a new and efficient way for preparing diindolylmethane derivatives.

参考文献

[1] Yamamoto, H. Lewis Acids in Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2000.
[2] Ye, J.-H.; Xu, G.-J.; Zhang, W.-C.; Wang, S.-B. Chin. J. Org. Chem. 2009, 29, 1664 (in Chinese).
(叶家海, 徐国际, 张文超, 田桂蓉, 有机化学, 2009, 29, 1664.)
[3] Wu, J.-Y.; Fang, H.; Xu, W.-F. Chin. J. Org. Chem. 2009, 29, 1175 (in Chinese).
(吴记勇, 芳浩, 徐文方, 有机化学, 2009, 29, 1175.)
[4] Zhao, Y.; Ye, C.-C.; Tan, X..-Y.; Yang, Z. Chin. J. Org. Chem. 2009, 29, 643 (in Chinese).
(赵莹, 叶翠层, 谭晓叶, 扬志, 有机化学, 2009, 29, 643.)
[5] Hollis, T. K.; Robison, N. P.; Bosnich, B. Tetrahedron Lett. 1992, 33, 6423.
[6] Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
[7] Ohmori, K.; Hatakeyama, K.; Ohrui, H.; Suzuki, K. Tetrahedron 2004, 60, 1365.
[8] Hollis, T. K.; Robinson, N. P.; Bosnich, B. Organometallics 1992, 11, 2745
[9] An, D.; Peng, Z.; Orita, A.; Kurita, A.; Man, S.; Ohkubo, K.; Li, X.; Fukuzumi, S.; Otera, J. Chem. Eur. J. 2006, 12, 1642.
[10] Qiu, R. H.; Xu, X. H.; Li, Y. H.; Zhang, G. P.; Shao, L. L.; An, D. L.; Yin, S. F. Chem. Commun. 2009, 1679.
[11] Qiu, R. H.; Zhang, G. P.; Zhu, Y. Y.; Xu, X. H.; Shao, L. L.; Li, Y. H.; An, D. L.; Yin, S. F. Chem. Eur. J. 2009, 15, 6488.
[12] Qiu, R. H.; Zhang, G. P.; Xu, X. H.; Zou, K. B.; Shao, L. L.; Fang, D. W.; Li, Y. H.; Orita, A.; Saijo, R.; Mineyama, H.; Suenobu, T.; Fukuzumi, S.; An, D. L.; Otera, J. J. Organomet. Chem. 2009, 1524.
[13] Qiu, R. H.; Zhu, Y. Y.; Xu, X. H.; Li, Y. H.; Shao, L. L.; Ren, X. F.; Cai, X. T.; An, D. L.; Yin, S. F. Catal. Commun. 2009, 10, 1889.
[14] Qiu, R. H.; Yin, S. F.; Zhang, X. W.; Xia, J.; Xu, X. H.; Luo, S. L. Chem. Commun. 2009, 4759.
[15] Qiu, R. H.; Zhang, G. P.; Xu, X. H.; Peng, L. F.; Zhao, Y. L.; Li, N. B.; Yin, S. F. Chem. Eur. J. 2012, 18, 6172.
[16] Mi, X. L.; Luo, S. Z.; He, J. Q. Tetrahedron Lett. 2004, 45, 4567.
[17] Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. A. J. Mol. Catal. A: Chem. 2006, 244, 168.
[18] Firouzabadi, H.; Iranpoor, N.; Jafarpour, M. J. Mol. Catal. A: Chem. 2006, 253, 249.
[19] Aliyan, H.; Fazaeli, R.; Naghash, H. J. Heteroat. Chem. 2009, 20, 325.
[20] Ma, Z. H.; Han, H. B.; Zhou, Z. B. J. Mol. Catal. A: Chem. 2009, 311, 46.
[21] Khaksar, S.; Ostad, S. M. J. Fluorine Chem. 2011, 132, 937.
[22] Lv, W.-H.; Liu, X.-H.; Liu, D.-Y. Chin. J. Catal. 2009, 30, 1287 (in Chinese).
(吕文辉, 刘兴海, 刘冬妍, 催化学报, 2009, 30, 1287.)
文章导航

/