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2021 , Vol. 41 >Issue 1: 407 - 411

DOI: https://doi.org/10.6023/cjoc202007011

研究简报

炔丙醇与烯醇硅醚的直接亲核取代反应

  • 李鑫玲 ,
  • 刘会丽 ,
  • 张顺吉
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  • a 淮北师范大学化学与材料科学学院 安徽淮北 235000
* Corresponding authors. E-mail:

收稿日期: 2020-07-04

  修回日期: 2020-08-06

  网络出版日期: 2020-08-27

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Direct Nucleophilic Substitution of Propargyl Alcohols with Enoxysilanes

  • Xinling Li ,
  • Huili Liu ,
  • Shunji Zhang
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  • a Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000

Received date: 2020-07-04

  Revised date: 2020-08-06

  Online published: 2020-08-27

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摘要

报道了一种在对甲苯磺酸催化下炔丙醇和烯醇硅醚的直接亲核取代反应, 并有效合成 γ-炔基酮类化合物的新方法. 该反应在敞口环境下使用未经干燥处理的溶剂即可获得良好的产率.

关键词： 炔丙醇; 烯醇硅醚; 亲核取代; 催化; 对甲苯磺酸

本文引用格式

李鑫玲 , 刘会丽 , 张顺吉 . 炔丙醇与烯醇硅醚的直接亲核取代反应[J]. 有机化学, 2021 , 41(1) : 407 -411 . DOI: 10.6023/cjoc202007011

Abstract

A novel and efficient synthesis of γ-alkynyl ketones by the direct nucleophilic substitution of propargyl alcohols with enoxysilanes in the presence of a catalytic amount of p-toluenesulfonic acid monohydrate, has been developed. The reactions can be performed in an undried solvent under an air atmosphere to obtain the desired products in good yields.

Key words： Keywords propargyl alcohol; enoxysilane; nucleophilic substitution; catalyzed; p-toluenesulfonic acid

参考文献

[1]
(a) Roy R.; Saha S. RSC Adv. 2018, 8, 31129.
[1]
(b) Zhu Y.; Sun L.; Lu P.; Wang Y. ACS Catal. 2014, 4, 1911.
[1]
(c) Ayers B.J.; Chan P.W.H. Synlett 2015, 26, 1305.
[1]
Zhang L.; Fang G.; Kumar R.K.; Bi X. Synthesis 2015, 47, 2317.
[1]
(e) Zhang X.X.; Lv C.; Li P.; Fu B. Chin. J. Org. Chem. 2016, 36, 1287. (in Chinese)
[1]
( 张小祥, 吕昌, 李萍, 付博, 姚薇薇, 有机化学, 2016, 36, 1287.).
[1]
(f) Lu F.D.; Jiang X.; Lu L.Q.; Xiao W.J. Acta Chim. Sinica 2019, 77, 803. (in Chinese)
[1]
( 路福东, 姜炫, 陆良秋, 肖文精, 化学学报, 2019, 77, 803.).
[2]
(a) Srihari P.; Bhunia D. C.; Sreedhar, P.; Mandal S. S.; Reddy J. S. S.; Yadav J. S.Tetrahedron Lett. 2007, 48, 8120.
[2]
(b) Luzung M.; Toste F. J. Am. Chem. Soc. 2003, 125, 15760.
[2]
(c) Georgy M.; Boucard V.; Campagne J. J. Am. Chem. Soc. 2005, 127, 14180.
[3]
Sanz R.; Miguel D.; Martínez A.; Álvarez-Gutiérrez J.; Rodríguez F. Org. Lett. 2007, 9, 727.
[4]
Mitsuhiro Y.; Tokutaro O.; Saki M.; Teruhisa Y.; Arisa S. Org. Lett. 2008, 10, 4251.
[5]
Matsuda I.; Komori K.; Itoh K. J. Am. Chem. Soc. 2002, 124, 9072.
[6]
Zhan Z.; Wang S.; Cai X.; Liu H.; Yu J.; Cui Y. Adv. Synth. Catal. 2007, 349, 2097.
[7]
Zhan Z.; Cai X.; Wang S.; Yu J.; Liu H.; Cui Y. J. Org. Chem. 2007, 72, 9838.
[8]
Lin M.; Hao L.; Ma R.; Zhan Z. Synlett 201 0, 2345.
[9]
Naveen N.; Koppolu S.; Balamurugan R. Adv. Synth. Catal. 2015, 357, 1463.
[10]
(a) Zhu H.; Ji K.; Yang F.; Wang L.; Zhao S.; Ali S.; Liu X.; Liang Y. Org. Lett. 2011, 13, 684.
[10]
(b) Zhang S.; Liu H. Chin. J. Org. Chem. 2020, 40, 1257. (in Chinese)
[10]
( 张顺吉, 刘会丽, 有机化学, 2020, 40, 1257.).
[10]
(c) Michael R., L.; Dean, T.J. Am. Chem. Soc. 200 3, 125, 15760.
[10]
(d) Zhou J.; Zhang G.; Zou J.; Zhang W. Eur. J. Org. Chem. 2011, 19, 3412.
[10]
(e) Lin C.; Duh T.; Lu W.; Lee J.; Lee C.; Chen C.; Wu M. J. Chin. Chem. Soc. 2004, 51, 183.
[10]
(f) Zhou C.; Dubrovsky A.; Larock R. J. Org. Chem. 2006, 71, 1626.
[10]
Tyrrell E.; Tesfa K.; Mann A.; Singh K. Synthesis, 2007, 1491.
[10]
(h) Li Z.; Pu L. Org. Lett. 20 04, 6, 1065.
[11]
(a) Cazeau P.; Duboudin F.; Moulines F.; Babot O.; Dunogues J. Tetrahedron 1986, 43, 2075.
[11]
(b) Leijondahl K.; Boren L.; Braun R.; Baeckvall J. Org. Lett. 2008, 10, 2027.
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