研究论文

五氟乙基硫叶立德:一类新的亲电五氟乙基化试剂

  • 刘亚飞 ,
  • 葛航铭 ,
  • 吕龙 ,
  • 沈其龙
展开
  • a 中国科学院上海有机化学研究所 中国科学院有机氟化学重点实验室 分子合成科学卓越研究中心 中国科学院大学 上海 200032;
    b 中国科学院上海有机化学研究所 上海 200032

收稿日期: 2018-07-09

  修回日期: 2018-08-02

  网络出版日期: 2018-09-10

基金资助

国家自然科学基金(Nos.21625206,21632009,21572258,21572259,21421002)、中国科学院战略性先导科技专项B类(No.XDB20000000)资助项目.

Pentafluoroethyl-Substituted Sulfonium Ylides: New Electrophilic Pentafluoroethylating Reagents

  • Liu Yafei ,
  • Ge Hangming ,
  • Lu Long ,
  • Shen Qilong
Expand
  • a Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032;
    b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2018-07-09

  Revised date: 2018-08-02

  Online published: 2018-09-10

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21625206, 21632009, 21572258, 21572259, 21421002) and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDB20000000).

摘要

发展了两个基于硫叶立德骨架的亲电五氟乙基化试剂,其合成高效简洁、固体状态下稳定而溶液中反应活性高.在温和条件下,该试剂可以与β-酮酸酯、芳基/杂芳基碘化物以及富电子芳烃反应高产率地得到相应的五氟乙基化产物.

本文引用格式

刘亚飞 , 葛航铭 , 吕龙 , 沈其龙 . 五氟乙基硫叶立德:一类新的亲电五氟乙基化试剂[J]. 有机化学, 2019 , 39(1) : 257 -264 . DOI: 10.6023/cjoc201807018

Abstract

Two electrophilic pentafluoroethylating reagents of pentafluoroethyl(p-methylphenyl)sulfonium bis(carbometh- oxy)methylide (4a) and pentafluoroethyl(4-nitrophenyl)sulfonium bis(carbomethoxy)methylide (4b), and their reactions under mild conditions with β-ketoesters, aryl iodides and heteroaromatics are described.

参考文献

[1] Liu, Y.-F.; Shao, X.-X.; Zhang, P.-P.; Shen, Q. Org. Lett. 2015, 17, 2752.
[2] (a) Trost, B. M.; Melvin, L. S. Sulfur Ylide:Emerging Synthetic Intermediates, Academic Press, New York, 1975.
(b) Aggrawal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
(c) Tang, Y.; Ye, S.; Sun, X-L. Synlett 2005, 18, 2720.
(d) Burtoloso, A. C. B.; Dias, R. M. P.; Leonarczyk, I. A. Eur.-J. Org. Chem. 2013, 5005.
[3] Zhu, J.-S.; Liu, Y.-F.; Shen, Q. Angew. Chem., Int. Ed. 2016, 55, 9050.
[4] Liu, Y.-F.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2017, 56, 9930.
[5] (a) Yagupolskii, L. M.; Mironova, I. I.; Maletina, I. I.; Orda, V. V. Synthesis 1978, 835.
(b) Yagupolskii, L. M. J. Fluorine Chem. 1987, 36, 1.
(c) Umemoto, T.; Kuriu, Y.; Shuyama, H.; Miyano, O.; Nakayama, S. I. J. Fluorine Chem. 1982, 80, 695.
(d) Umemoto, T.; Kuriu, Y.; Shuyama, H.; Miyano, O.; Nakayama, S. I. J. Fluorine Chem. 1986, 31, 37.
(f) Zhdankin, V. V.; Kuehl, C. J. Tetrahedron Lett. 1994, 35, 1809.
(g) Umemoto, T.; Kuriu, T. Tetrahedron Lett. 1981, 22, 5197.
(h) Umemoto, T.; Kuriu, T. Chem. Lett. 1982, 65.
[6] Liu, Q.-H.; Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2014, 79, 10434.
[7] Zhu, J.-S.; Li, Y.-G.; Ni, C.-F.; Shen, Q. Chin. J. Chem. 2016, 34, 662.
[8] Boiko, V. N.; Shchupak, G. M. J. Fluorine Chem. 1994, 3, 207.
[9] Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Angew. Chem., Int. Ed. 2011, 50, 1896.
[10] (a) Cheng, Y.-Z.; Yu, S.-Y. Org. Lett. 2016, 18, 2962.
(b) Cheng, Y.-Z.; Yuan, X.-G.; Ma, J.; Yu. S.-Y. Chem.-Eur. J. 2015, 21, 8355.
[11] Huang, Y.-J.; Ajitha, M. J.; Huang, K.-W.; Zhang, Z.-X.; Weng, Z.-Q. Dalton Trans. 2016, 45, 8468.

文章导航

/