Citation: Bai Xiaodong, Fu Zhihong, Cao Yucai, Lin Jinhong. Trifluoromethanesulfonylation of Phenols[J]. Chinese Journal of Organic Chemistry, ;2020, 40(4): 1028-1032. doi: 10.6023/cjoc201911026 shu

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

Corresponding author: Fu Zhihong, 1160757400@qq.com Lin Jinhong, jlin@sioc.ac.cn
Received Date: 22 November 2019
Revised Date: 27 December 2019
Available Online: 3 January 2020
Fund Project: the Fujian Institute of Innovation, CAS FJCXY18040102the National Natural Science Foundation of China 21971252the Youth Innovation Promotion Association CAS 2019256the Shanghai Research Institute of Chemical Industry Co., LTD. SKL-LCTP-201802the National Natural Science Foundation of China 21421002Project 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)the Key Research Program of Frontier Sciences, Chinese Academy of Sciences (CAS) QYZDJSSW-SLH049the National Natural Science Foundation of China 51104122the National Natural Science Foundation of China 21672242

Figures(2)

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·CF₃SO₃^-) 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.
- aryl triflates,
- trifluoromethanesulfonylation,
- phenols,
- trifluoromethanesulfonyl pyridinium salt,
- fluorine
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