Synthesis of ArCF2X and [18F]Ar-CF3 via Cleavage of the Trifluoromethylsulfonyl Group

A versatile synthesis of ArCF2X and [18F]­Ar-CF3 type compounds from readily available ArCF2SO2CF3 has been developed. Diverse nucleophiles, including weak nucleophiles such as halides (18F–, Cl–, Br–, and I–), RSH, and ROH, could react with ArCF2SO2CF3 efficiently to give the corresponding difluoro...

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Bibliographic Details
Published in:Organic letters 2022-01, Vol.24 (1), p.164-168
Main Authors: Yang, Ren-Yin, Gao, Xinyan, Gong, Kehao, Wang, Juan, Zeng, Xiaojun, Wang, Mingwei, Han, Junbin, Xu, Bo
Format: Article
Language:English
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Summary:A versatile synthesis of ArCF2X and [18F]­Ar-CF3 type compounds from readily available ArCF2SO2CF3 has been developed. Diverse nucleophiles, including weak nucleophiles such as halides (18F–, Cl–, Br–, and I–), RSH, and ROH, could react with ArCF2SO2CF3 efficiently to give the corresponding difluoromethylene products. The control experiments and the Hammett plot indicated that the reaction might proceed through a difluorocarbocation intermediate generated from the steric hindrance-assisted cleavage of the trifluoromethylsulfonyl group.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03803