NOTES

Direct Nucleophilic Substitution of Propargyl Alcohols with Enoxysilanes

  • Xinling Li ,
  • Huili Liu ,
  • Shunji Zhang
Expand
  • 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

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.

Cite this article

Xinling Li , Huili Liu , Shunji Zhang . Direct Nucleophilic Substitution of Propargyl Alcohols with Enoxysilanes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 407 -411 . DOI: 10.6023/cjoc202007011

References

[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.
Outlines

/