SIOC English
有机化学
高级检索

有机化学 >

2016 , Vol. 36 >Issue 5: 1094 - 1098

DOI: https://doi.org/10.6023/cjoc201510035

研究简报

三苯基铋全氟辛基磺酸盐催化β-氨基醇高效合成

  • 谭年元 ,
  • 王鹏辉 ,
  • 许新华 ,
  • 高青松 ,
  • 区泽棠 ,
  • 邱仁华
展开
  • a. 湖南工程学院化学化工学院 湘潭 411104;
    b. 湖南大学化学化工学院 长沙 410082;
    c. 湖北省纤维检验局 武汉 430061

收稿日期: 2015-10-29

  修回日期: 2016-01-21

  网络出版日期: 2016-01-29

基金资助

国家自然科学基金(No.21373003)、湖南省自然科学基金(No.14JJ7027)、湖南省教育厅重点(No.15A041)资助项目.

收起

Efficient Synthesis of β-Amino Alcohols Promoted by Triphenylbismuth Bisperfluorooctanesulfonates

  • Tan Nianyuan ,
  • Wang Penghui ,
  • Xu Xinhua ,
  • Gao Qingsong ,
  • Au Chaktong ,
  • Qiu Renhua
Expand
  • a. College of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104;
    b. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    c. Hubei Province Fibre Inspection Bureau, Wuhan 430061

Received date: 2015-10-29

  Revised date: 2016-01-21

  Online published: 2016-01-29

Supported by

Projected support by the National Natural Science Foundation of China (No. 21373003), the Natural Science Foundation of Hunan Province (No. 14JJ7027), and the Key Project of Hunan Province Education Department (No. 15A041).

Fold

摘要

本工作合成了一种新型的对空气稳定的路易斯酸性催化剂三苯基铋(V)全氟辛基磺酸盐,该催化剂由对水敏感的三苯基铋二氯化物与全氟辛基磺酸银在无水二氯甲烷溶剂中室温下反应制得.催化活性评价实验表明,在三苯基铋(V)全氟辛基磺酸盐(5.0mol%)存在下,室温和无溶剂条件下,环氧化合物和胺类的反应有效进行,较高产率地得到了β-氨基醇类化合物.催化剂在重复使用4次之后,反应产率无明显降低.本方法为β-氨基醇的制备提供了一条简单高效的途径.

关键词： 有机铋; 全氟辛基磺酸盐; 路易斯酸; β-氨基醇; 无溶剂合成

本文引用格式

谭年元 , 王鹏辉 , 许新华 , 高青松 , 区泽棠 , 邱仁华 . 三苯基铋全氟辛基磺酸盐催化β-氨基醇高效合成[J]. 有机化学, 2016 , 36(5) : 1094 -1098 . DOI: 10.6023/cjoc201510035

Abstract

In this paper, a novel air-stable triphenylbismuth bisperfluorooctanesulfonate was synthesized by treatment of moisture-sensitive triphenylbismuth dichloride with silver bisperfluorooctanesulfonate in anhydrous CH2Cl2 at room temperature. Its catalytic assessment results show that the reactions of arylamine and epoxide proceed efficiently in the presence of triphenylbismuth bisperfluorooctanesulfonates 1(5.0 mol%) under solvent-free condition, affording β-amino alcohols in good to excellent yields. The yields of desired products do not reduce obviously after recycling for 4 times of catalyst 1. Hence, a convenient and efficient method for preparation of β-amino alcohols is provided.

Key words： organobismuth; perfluorooctanesulfonate; Lewis acid; β-amino alcohol; solvent-free synthesis

参考文献

[1] Métro, T.-X.; Appenzeller, J.; Pardo, D. G.; Cossy, J. Org. Lett. 2006, 8, 3509.
[2] Métro, T.-X.; Pardo, D. G.; Cossy, J. J. Org. Chem. 2007, 72, 6556.
[3] Tan, W.; Zhao, B.-X.; Sha, L.; Jiao, P.-F.; Wan, M.-S.; Su, L. Chin. J. Org. Chem. 2005, 25, 1011 (in Chinese).
(谭伟, 赵宝祥, 沙磊, 焦培福, 万茂生, 苏磊, 有机化学, 2005, 25, 1011.)
[4] Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703.
[5] Tanaka, Y.; Taniguchi, N.; Uemura, M. Org. Lett. 2002, 4, 835.
[6] Liu, W.-M.; Wang, P.-A.; Zhang, S.-Y.; Jiang, R. Chin. J. Org. Chem. 2006, 26, 518 (in Chinese).
(柳文敏, 王平安, 张生勇, 姜茹, 有机化学, 2006, 26, 518.)
[7] Pan, S. Q.; Zhang, C. H.; Li, Y.; Yan, S. J.; Lin, J. Chin. J. Org. Chem. 2011, 31, 193 (in Chinese).
(潘圣强, 张从海, 李烨, 严胜骄, 林军, 有机化学, 2011, 31, 193.)
[8] Yang, F. F.; Gu, X. F.; Yang, L.; Gao, Y. H.; Lu, H. F. Fine Chem. 2013, 30, 956 (in Chinese).
(杨飞飞, 顾晓峰, 杨林, 高玉华, 陆鸿飞, 精细化工, 2013, 30, 956.)
[9] Reddy, L. R.; Reddy, M. A.; Bhanumathi, N.; Rao, K. R. New J. Chem. 2001, 25, 221.
[10] Ollevier, T.; Lavie-Compin, G. Tetrahedron Lett. 2002, 43, 7891.
[11] Thirupathaiah, A.; Ramanna, S.; Rao, G. V. Orient. J. Chem. 2009, 25, 165.
[12] Chakraborti, A. K.; Kondaskar, A. Tetrahedron Lett. 2003, 44, 8315.
[13] Swamy, N. R.; Goud, T. V.; Reddy, S. M.; Krishnaiah, P.; Venkateswarlu, Y. Synth. Commun. 2004, 34, 727.
[14] Singh, M. C.; Peddinti, R. K. Tetrahedron Lett. 2007, 48, 7354.
[15] Pachón, L. D.; Gamez, P.; Brussel. J. J. M.; Reedijk, J. Tetrahedron Lett. 2003, 44, 6025.
[16] Kamal, A.; Prasad, B. R.; Reddy, A. M.; Khan, M. N. A. Catal. Lett. 2007, 8, 1876.
[17] Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Venkat Narsaiah, A. Tetrahedron Lett. 2003, 44, 1047.
[18] Azizi, N.; Saidi, M. R. Tetrahedron 2007, 63, 888.
[19] Kureshy, R. I.; Singh, S.; Khan, N. H.; Abdi, S. H. R.; Suresh, E.; Jasra, R. V. J. Mol. Catal. A: Chem. 2007, 264, 162.
[20] Sreedhar, B.; Radhika, P.; Neelima, B.; Hebalkar, N. J. Mol. Catal. A: Chem. 2007, 272, 159.
[21] Bordoloi, A.; Hwang, Y. K.; Hwang, J-S.; Halligudi, S. B. Catal. Commun. 2009, 10, 1398.
[22] Danafar, H.; Yadollahi, B. Catal. Comm. 2009, 10, 842.
[23] Heravi, M. M.; Bakhtiari, K.; Alinejhad, H.; Saeedi, M.; Malakooti, R. Chin. J. Chem. 2010, 28, 269.
[24] Yin, S. F.; Maruyama, J.; Yamashita, T.; Shimada, S. Angew. Chem., Int. Ed. 2008, 47, 6590.
[25] De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2005, 46, 8345.
[26] Thirupathaiah, A.; Rao, G. V. Indian J. Chem. 2008, 47B, 1762.
[27] Hollis, T. K.; Robison, N. P.; Bosnich, B. Tetrahedron Lett. 1992, 33, 6423.
[28] Li, X. S.; Kurita, A.; Man-E, S.; Orita, A.; Otera, J. Organometallics 2005, 24, 2567.
[29] An, D. L.; Peng, Z. H.; Orita, A.; Kurita, A.; Man-e, S.; Ohkubo, K.; Li, X. S.; Fukuzumi, S.; Otera, J. Chem. Eur. J. 2006, 12, 1642.
[30] Qiu, R. H.; Xu, X. H.; Peng, L. F.; Zhao, Y. L.; Li, N. B.; Yin, S. F. Chem. Eur. J. 2012, 18, 6172.
[31] Li, N. B.; Wang, J. Y.; Zhang, X. H.; Qiu, R. H.; Wang, X.; Chen, J. Y.; Yin, S. F.; Xu, X. H. Dalton Trans. 2014, 43, 11696.
[32] Zhang, X. H.; Qiu, R. H.; Zhou, C. C.; Yu, J. X.; Li, N. B.; Yin, S. F.; Xu, X. H. Tetrahedron 2015, 71, 1011.
[33] Placzek, A. T.; Donelson, J. L.; Trivedi, R.; Gibbs, R. A.; De, S. K. Tetrahedron Lett. 2005, 46, 9029.
[34] Wang, P. H.; Wang, J. Y.; Au, C.-T.; Qiu, R. H.; Xu, X. H.; Yin, S. F. Adv.Synth. Catal.2016, 358, 1302.
[35] Simona, B.; Francesco, F.; Ferdinando, P.; Luigi, V. Synlett 2007, 2683.
[36] Qiu, R. H.; Wang, P. H.; Wang, J. Y.; Zhu, L. Z.; Yin, S. F.; Xu, X. H.CN 105131041, 2015.
[37] Danafar, H.; Yadollahi, B. Catal. Commun. 2009, 10, 842.

Options
文章导航

/

〈 〉