Chinese Journal of Organic Chemistry >
Pentafluoroethyl-Substituted Sulfonium Ylides: New Electrophilic Pentafluoroethylating Reagents
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).
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.
Key words： fluorine; pentafluoroethyl; sulfonium ylide; electrophilic
Liu Yafei , Ge Hangming , Lu Long , Shen Qilong . Pentafluoroethyl-Substituted Sulfonium Ylides: New Electrophilic Pentafluoroethylating Reagents[J]. Chinese Journal of Organic Chemistry, 2019 , 39(1) : 257 -264 . DOI: 10.6023/cjoc201807018
[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.
/
| 〈 |
|
〉 |
