SIOC English
有机化学
高级检索

有机化学 >

2019 , Vol. 39 >Issue 10: 2941 - 2945

DOI: https://doi.org/10.6023/cjoc201903075

研究简报

铁氢配合物对一级酰胺脱水成腈的催化作用

  • 郑婷婷 ,
  • 王洋洋 ,
  • 杨在孝 ,
  • 孙宏建 ,
  • 李晓燕
展开
  • a 山东大学化学与化工学院 教育部特种功能聚集体材料重点实验室 济南 250100
    b 首都师范大学化学系 北京 100048
    c 西北师范大学化学化工学院 兰州 730070

收稿日期: 2019-03-30

  修回日期: 2019-06-03

  网络出版日期: 2019-07-03

基金资助

国家自然科学基金;国家自然科学基金(No. 21372143)

收起

Catalytic Effect of Iron Hydrides on Dehydration of Primary Amides to Nitriles

  • Tingting Zheng, ,
  • Yangyang Wang, ,
  • Zaixiao Yang, ,
  • Hongjian Sun, ,
  • Xiaoyan Li,
Expand
  • a Key Laboratory of Special Functional Aggregated Materials, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100
    b Department of Chemistry, Capital Normal University, Beijing 100048
    c College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received date: 2019-03-30

  Revised date: 2019-06-03

  Online published: 2019-07-03

Supported by

Project supported by the National Natural Science Foundation of China;Project supported by the National Natural Science Foundation of China(No. 21372143)

Fold

摘要

主要研究了苯硒酚基铁氢配合物cis-[(ArSe)FeH(PMe3)4] [Ar=Ph (1), p-MeOC6H4 (2)和o-MeC6H4 (3)]对一级酰胺脱水成腈的催化作用. 实验证明当选用(EtO)3SiH为还原剂时, 在较为温和的条件下这三种配合物均对一级酰胺脱水为腈的过程都具有良好的催化作用. 该催化体系对于芳基酰胺中苯环上的取代基具有很好的耐受性. 与斥电性基团相比, 吸电性基团对该催化反应比较有利.

关键词： 铁氢配合物; 硒酚; 硒配位; 酰胺脱水; 腈制备

本文引用格式

郑婷婷 , 王洋洋 , 杨在孝 , 孙宏建 , 李晓燕 . 铁氢配合物对一级酰胺脱水成腈的催化作用[J]. 有机化学, 2019 , 39(10) : 2941 -2945 . DOI: 10.6023/cjoc201903075

Abstract

Three cis-selenophenolato iron hydrides [cis-[(ArSe)FeH(PMe3)4] (Ar=Ph (1), p-MeOC6H4 (2) and o-MeC6H4 (3)], were used as catalysts for the dehydration of primary amides to nitriles. The experimental results show that three complexes have good catalytic effect on reductive dehydration of primary amide to nitrile under mild conditions using (EtO)3SiH as reducing agent. The catalytic system is well tolerated to the substituents on the benzene ring in aromatic amides. Compared with electron-donating group, electron-withdrawing group is more advantageous to the catalytic reaction.

Key words： iron hydride; selenophenol; Se-coordination; reductive amide dehydration; nitrile preparation

参考文献

[1] Mowry, D. T. Chem. Rev. 1948, 42, 189.
[2] Kukushkin, V. Y.; Pombeiro, J. L. Chem. Rev. 2002, 102, 1771.
[3] Gaspar, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 4519.
[4] Kent, R. E.; McElvain, S. M. Org. Synth. 1945, 25, 61.
[5] Krynitsky, J. A.; Carhart, H. W. Org. Synth. Coll. 1963, IV, 436.
[6] Reisner, D. B.; Horning, E. C. Org. Synth. Coll. 1963, IV, 144.
[7] Kuwano, R.; Takahashi, M.; Ito, Y. .Tetrahedron Lett 1998, 39, 1017.
[8] Das, S.; Zhou, S.; Addis, D.; Enthaler, S.; Junge, K.; Beller, M. . Top. Catal 2010, 53, 979.
[9] Park, S.; Brookhart, M. J. Am. Chem. Soc. 2012, 134, 640.
[10] Pisiewicz, S.; Junge, K.; Beller, M . Eur. J. Inorg. Chem. 2014,2345.
[11] Ren, S.; Wang, Y.; Yang, F.; Sun, H.; Li, X. . Catal. Commun 2019, 120, 72.
[12] Bose, D. S.; Jayalakshmi, B.; Goud, P. R . Synthesis 1999,1724.
[13] Manjula, K.; Pasha, M. A. Synth. Commun. 2007, 37, 1545.
[14] Enthaler, S.; Weidauer, M. . Catal. Lett 2011, 141, 1079.
[15] Enthaler, S. Eur. J. Org. Chem. 2011, 2011, 4760.
[16] Elangovan, S.; Quintero-Duque, S.; Dorcet, V.; Roisnel, T.; Norel, L.; Darcel, C.; Sortais, J.-B. Organometallics 2015, 34, 4521.
[17] Bezier, D.; Venkanna, G. T.; Sortais, J.-B.; Darcel, C. ChemCatChem 2011, 3, 1747.
[18] Xue, B.; Sun, H.; Wang, Y.; Zheng, T., Li, X.; Fuhr, O.; Fenske, D. .Catal. Commun 2016, 86, 148.
[19] Wang, Y.; Ren, S.; Zhang, W.; Xue, B.; Qi, X.; Sun, H.; Li, X.; Fuhr, O.; Fenske, D. .Catal. Commun 2018, 115, 1.
[20] Luan, H. X.; Sun, H. J.; Xue, B. J.; Li, X. Y. Chin. J. Org. Chem. 2017, 37, 1392 (in Chinese).
[20] ( 栾化鑫, 孙宏建, 薛本静, 李晓燕, 有机化学, 2017, 37, 1392.)
[21] Zhao, H.; Sun, H. J.; Wang, L.; Li, X. Y. Acta Chim. Sinica 2015, 73, 1307 (in Chinese).
[21] ( 赵华, 孙宏建, 王麟, 李晓燕, 化学学报 , 2015, 73, 1307.)
[22] Lu, F. G.; Sun, H. J.; Li, X. Y. Chin. J. Chem. 2013, 31, 927.
[23] Qi, X.; Sun, H.; Li, X.; Fuhr, O.; Fenske, D. . Dalton Trans 2018, 47, 2581.
[24] Qi, X.; Zheng, T.; Zhou, J.; Dong, Y.; Zuo, X.; Li, X.; Sun, H.; Fuhr, O.; Fenske, D. Organometallics 2019, 38, 268.
[25] Wang, Z.; Li, X.; Sun, H.; Fuhr, O.; Fenske, D. Organometallics 2018, 37, 539.
[26] Wang, L.; Sun, H.; Li, X. Organometallics 2015, 34, 5175.
[27] Zhou, H.; Sun, H.; Zhang, S.; Li, X. Organometallics 2015, 34, 1479.
[28] Liu, R. Y.; Bae, M.; Buchwald, S. L. J. Am. Chem. Soc. 2018, 140, 1627.
[29] Wang, Y. Y.; Fu, L. Y.; Qi, H. M.; Chen, S. W.; Li, Y. H . Asian J. Org. Chem. 2018,7, 367.
[30] Supsana, P.; Liaskopoulos, T.; Tsoungas, P. G.; Varvounis, G . Synlett 2007,2671.
[31] Ramanathan, A.; Jimenea, L. S . Synthesis 2010,217.
[32] Ushijima, S.; Moriyama, K.; Togo, H. Tetrahedron 2011, 67, 958.
[33] Kijima, M.; Nambu, Y.; Endo, T.; Okawara, M. J. Org. Chem. 1984, 49, 1434.
[34] Silverman, M.; Bogert, M. T. J. Org. Chem. 1946, 11, 34.
Options
文章导航

/

〈 〉