Journal
TETRAHEDRON LETTERS
Volume 58, Issue 7, Pages 690-693Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.01.018
Keywords
Sulfinate; Electrophilic trifluoromethylthiolation; Trifluoromethanesulfanylamide; Trifluoromethyl thiolsulphonate; Tandem reaction
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Funding
- Natural Science Foundation of China [21502069]
- Natural Science Foundation of Zhejiang Province [LQ15B020006]
- Ph.D. Scientific Research Starting Foundation of Jiaxing University [70515015]
- Shanghai Ocean University [A2-0203-00-100338]
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A novel and efficient tandem reaction of sulfonyl chloride and trifluoromethylsulfanylamide is described here for the synthesis of various trifluoromethyl thiolsulphonates with a broad functional group tolerance. In the process, it is believed that sulfinate generated from sulfonyl chloride is a critical intermediate and the additive 4-methylbenzenesulfonic acid (p-TsOH) facilitates the formation of CF3S'. Electrophilic trifluoromethylthiolation of in situ generated sulfinate and CF3S+ provides the final products. (C) 2017 Elsevier Ltd. All rights reserved.
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