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2020 , Vol. 40 >Issue 4: 1028 - 1032

DOI: https://doi.org/10.6023/cjoc201911026

研究简报

酚的三氟甲磺酰基化反应

  • 白小东 ,
  • 付志宏 ,
  • 曹育才 ,
  • 林锦鸿
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  • a 西南石油大学新能源与材料学院 成都 610500;
    b 中国科学院上海有机化学研究所 有机氟化学重点实验室 中国科学院大学 上海 200032;
    c 上海化工研究院有限公司 聚烯烃催化技术与高性能材料国家重点实验室 上海市聚烯烃催化技术重点实验室 上海 200062

收稿日期: 2019-11-22

  修回日期: 2019-12-27

  网络出版日期: 2020-01-03

基金资助

国家自然科学基金（Nos.21421002，21672242，21971252，51104122）、中国科学院前沿科学重点研究计划（No.QYZDJSSW-SLH049）、中国科学院青年创新促进会（No.2019256）、中国科学院福建创新研究院（No.FJCXY18040102）和上海化工研究院有限公司（No.SKL-LCTP-201802）资助项目.

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Trifluoromethanesulfonylation of Phenols

  • Bai Xiaodong ,
  • Fu Zhihong ,
  • Cao Yucai ,
  • Lin Jinhong
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  • a School of New Energy and Materials, Southwest Petroleum University, Chengdu 610500;
    b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032;
    c State Key Laboratory of Polyolefins and Catalysis, Shanghai Key Laboratory of Catalysis Technology for Polyolefins, Shanghai Research Institute of Chemical Industry Co. Ltd., Shanghai 200062

Received date: 2019-11-22

  Revised date: 2019-12-27

  Online published: 2020-01-03

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21421002, 21672242, 21971252, 51104122), the Key Research Program of Frontier Sciences, Chinese Academy of Sciences (CAS) (No. QYZDJSSW-SLH049), the Youth Innovation Promotion Association CAS (No. 2019256), the Fujian Institute of Innovation, CAS (No. FJCXY18040102), and the Shanghai Research Institute of Chemical Industry Co., LTD. (No. SKL-LCTP-201802).

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摘要

三氟甲磺酸芳基酯在有机合成和药物化学中有重要应用，因而如何实现高效制备吸引了不少关注.三氟甲磺酰基吡啶盐（C5H5N+SO2CF3·CF3SO-3）可作为温和的三氟甲磺酰基化试剂，与酚类化合物反应得到三氟甲磺酸芳基酯.产物的纯化只需简单洗涤，不需要繁琐的柱层析操作.除了芳基酯，烯基酯也能由该吡啶盐为试剂合成得到.吡啶盐的制备和分离容易，干燥环境中稳定存在，使用起来方便.

关键词： 三氟甲磺酸芳基酯; 三氟甲磺酰基化; 酚; 三氟甲磺酰基吡啶盐; 氟

本文引用格式

白小东 , 付志宏 , 曹育才 , 林锦鸿 . 酚的三氟甲磺酰基化反应[J]. 有机化学, 2020 , 40(4) : 1028 -1032 . DOI: 10.6023/cjoc201911026

Abstract

As aryl triflates are widely used in organic synthesis and medicinal chemistry, significant efforts have been directed towards the development of efficient methods for their synthesis. It was found that trifluoromethanesulfonyl pyridinium salt (C5H5N+SO2CF3·CF3SO-3) was able to act as a mild trifluoromethanesulfonylation reagent to convert phenols into aryl triflates. All aryl triflate products could be purified simply by washing, and tedious chromatography operations were avoided. Besides aryl triflates, vinyl triflates could also be synthesized by using this pyridinium salt as reagent. The pyridinium salt could be easily prepared and purified, is stable under dry atmosphere, and thus may become an easy-to-handle reagent.

Key words： aryl triflates; trifluoromethanesulfonylation; phenols; trifluoromethanesulfonyl pyridinium salt; fluorine

参考文献

[1] (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
(b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
(c) Zhang, M.; Chen, B.; Ge, C.; Liu, R.; Gao, J.; Jia, Y. Chin. J. Org. Chem. 2016, 36, 1636(in Chinese). (张鸣頔, 陈斌, 葛晨, 刘人荣, 高建荣, 贾义霞, 有机化学, 2016, 36, 1636.)
[2] (a) Moriconi, A.; Bigogno, C.; Bianchini, G.; Caligiuri, A.; Resconi, A.; Dondio, M. G.; D'Anniballe, G.; Allegretti, M. ACS Med. Chem. Lett. 2011, 2, 768.
(b) Broccatelli, F.; Mannhold, R.; Moriconi, A.; Giuli, S.; Carosati, E. Mol. Pharm. 2012, 9, 2290.
[3] (a) Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550.
(b) Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140.
(c) Dubrovskiy, A. V.; Markina, N. A.; Larock, R. C. Org. Biomol. Chem. 2013, 11, 191.
[4] (a) Pialat, A.; Liegault, B.; Taillefer, M. Org. Lett. 2013, 15, 1764.
(b) Yang, Z.-W.; Zhang, Q.; Jiang, Y.-Y.; Li, L.; Xiao, B.; Fu, Y. Chem. Commun. 2016, 52, 6709.
(c) Nakazawa, H.; Sako, M.; Masui, Y.; Kurosaki, R.; Yamamoto, S.; Kamei, T.; Shimada, T. Org. Lett. 2019, 21, 6466.
[5] Norihiko, Y.; Tsuyoshi, F.; Takao, M.; Akira, S. Chem. Lett. 1991, 20, 459.
[6] (a) Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85.
(b) Ritter, K. Synthesis 1993, 735.
[7] Seganish, W. M.; DeShong, P. J. Org. Chem. 2004, 69, 1137.
[8] (a) Qing, F.-L.; Fan, J.; Sun, H.-B.; Yue, X.-J. J. Chem. Soc., Perkin Trans. 11997, 3053.
(b) Frantz, D. E.; Weaver, D. G.; Carey, J. P.; Kress, M. H.; Dolling, U. H. Org. Lett. 2002, 4, 4717.
(c) Gill, D.; Hester, A. J.; Lloyd-Jones, G. C. Org. Biomol. Chem. 2004, 2, 2547.
[9] Effenberger, F.; Mack, K. E. Tetrahedron Lett. 1970, 11, 3947.
[10] (a) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 14, 4607.
(b) Bengtson, A.; Hallberg, A.; Larhed, M. Org. Lett. 2002, 4, 1231.
[11] Zhu, J.; Bigot, A.; Elise, M.; Dau, T. H. Tetrahedron Lett. 1997, 38, 1181.
[12] Wentworth, A. D.; Wentworth, P.; Mansoor, U. F.; Janda, K. D. Org. Lett. 2000, 2, 477.
(b) Chung, C. W. Y.; Toy, P. H. Tetrahedron 2005, 61, 709.
[13] (a) White, K. L.; Mewald, M.; Movassaghi, M. J. Org. Chem. 2015, 80, 7403.
(b) Yogendra, S.; Hennersdorf, F.; Bauzá, A.; Frontera, A.; Fischer, R.; Weigand, J. J. Chem. Commun. 2017, 53, 2954.
[14] Wu, J.; Lu, C.; Lu, L.; Shen, Q. Chin. J. Chem. 2018, 36, 1031.
[15] Takeshi, K.; Hideki, K.; Takeshi, F.; Rieko, T.; Takashi, T.; Koji, S.; Naokid, T. US 2011/112103, 2011.
[16] Ma, X.; Dang, H.; Rose, J. A.; Rablen, P.; Herzon, S. B. J. Am. Chem. Soc. 2017, 139, 5998.
[17] James M. B.; Daniel C. B.; Timothy, B.; Allen, B. WO 2017/218922, 2017.
[18] Qin, L.; Ren, X.; Lu, Y.; Li, Y.; Zhou, J. Angew. Chem., Int. Ed. 2012, 51, 5915.
[19] Scheidt, F.; Neufeld, J.; Schäfer, M.; Thiehoff, C.; Gilmour, R. Org. Lett. 2018, 20, 8073.
[20] Chao, J.; Istvan J. E.; Kevin, G.; Richard, H. WO 2014/8214, 2014.
[21] Su, N.; Theorell, J. A.; Wink, D. J.; Driver, T. Angew. Chem., Int. Ed. 2015, 54, 12942.
[22] Picado, A; Li, S.; Dieter, R. K. J. Org. Chem. 2016, 81, 1391.
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