Trifluoromethanesulfonylation of Phenols

doi:10.6023/cjoc201911026

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 1028-1032.DOI: 10.6023/cjoc201911026 Previous Articles Next Articles

酚的三氟甲磺酰基化反应

白小东^a, 付志宏^a, 曹育才^c, 林锦鸿^b

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 发布日期:2020-01-03
通讯作者: 付志宏, 林锦鸿 E-mail:1160757400@qq.com;jlin@sioc.ac.cn
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.

Trifluoromethanesulfonylation of Phenols

Bai Xiaodong^a, Fu Zhihong^a, Cao Yucai^c, Lin Jinhong^b

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:2019-11-22 Revised:2019-12-27 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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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

Cite this article

Bai Xiaodong, Fu Zhihong, Cao Yucai, Lin Jinhong. Trifluoromethanesulfonylation of Phenols[J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 1028-1032.

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[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.

酚的三氟甲磺酰基化反应

Trifluoromethanesulfonylation of Phenols

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