Citation: Liu Zhuo, Long Jin, Xiao Xuan, Lin Jin-Hong, Zheng Xing, Xiao Ji-Chang, Cao Yu-Cai. Ph₃P⁺CF₂CO₂^- as an F^- and: CF₂ source for trifluoromethylthiolation of alkyl halides[J]. Chinese Chemical Letters, ;2019, 30(3): 714-716. doi: 10.1016/j.cclet.2018.11.013 shu

Ph₃P⁺CF₂CO₂^- as an F^- and: CF₂ source for trifluoromethylthiolation of alkyl halides

Liu Zhuo ^a,b ,
Long Jin ^a,b ,
Xiao Xuan ^a,b ,
Lin Jin-Hong ^b,*, ,
Zheng Xing ^a,*, ,
Xiao Ji-Chang ^b,*, ,
Cao Yu-Cai ^c

a.
Institute of Pharmacy and Pharmacology, Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, University of South China, Hengyang 421001, China
b.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
c.
Shanghai Research Institute of Chemical Industry Co., LTD., Shanghai 200062, China

jlin@sioc.ac.cn

zhengxing9166@sohu.com

jchxiao@sioc.ac.cn

Received Date: 9 October 2018
Revised Date: 27 October 2018
Accepted Date: 12 November 2018
Available Online: 13 March 2018

Figures(4)

As trifluoromethylthiolation has received increasing attention recently, many CF₃S-reagents and trifluoromethylthiolation methods have been developed. Herein we describe trifluoromethylthiolation of alkyl halides by using Ph₃P⁺CF₂CO₂^- as a fluoride and difluorocarbene source. Difluorocarbene is a versatile intermediate, but its side reactions are usually ignored and the by-products would therefore be discarded. In this work, a side reaction of difluorocarbene, the generation of a fluoride anion from difluorocarbene, was developed into a synthetic tool. Although the trifluoromethylthiolation reaction involved multi-sequential steps, the cleavage of C-F bond, the formation of CF₂=S bond, F-C(S)F₂ bond, and C-SCF₃ bond, the conversion proceeded fast and was completed within 10 min.
- Difluorocarbene,
- Trifluoromethylthiolation,
- Alkyl halides,
- Thiocarbonyl fluoride,
- Fluorine
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沈阳化工大学材料科学与工程学院沈阳 110142

Ph3P+CF2CO2- as an F- and: CF2 source for trifluoromethylthiolation of alkyl halides

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Ph₃P⁺CF₂CO₂^- as an F^- and: CF₂ source for trifluoromethylthiolation of alkyl halides