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Difluorocarbene‐Derived Trifluoromethylthiolation and [ 18 F]Trifluoromethylthiolation of Aliphatic Electrophiles
Author(s) -
Zheng Jian,
Wang Lu,
Lin JinHong,
Xiao JiChang,
Liang Steven H.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201505446
Subject(s) - difluorocarbene , electrophile , fluoride , chemistry , fluorine , alkyl , molecule , functional group , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis , polymer
The first trifluoromethylthiolation and [ 18 F]trifluoromethylthiolation of alkyl electrophiles with in situ generated difluorocarbene in the presence of elemental sulfur and external (radioactive) fluoride ion is described. This transition‐metal‐free approach is high yielding, compatible with a variety of functional groups, and operated under mild reaction conditions. The conceptual advantage of this exogenous‐fluoride‐mediated transformation enables unprecedented syntheses of [ 18 F]CF 3 S‐labeled molecules from most commonly used [ 18 F]fluoride ions. The rapid radiochemical reaction time (≤1 min) and high functional‐group tolerance allow access to a variety of aliphatic [ 18 F]CF 3 S compounds in high yields.