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Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

ABSTRACT: 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]CF3S-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]CF3S compounds in high yields.

SUBMITTER: Zheng J

PROVIDER: S-EPMC4692268 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Difluorocarbene-Derived Trifluoromethylthiolation and [(18)F]Trifluoromethylthiolation of Aliphatic Electrophiles.

Zheng Jian J Wang Lu L Lin Jin-Hong JH Xiao Ji-Chang JC Liang Steven H SH

Angewandte Chemie (International ed. in English) 20150921 45

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]CF3S-label ...[more]

PMID: 26387796

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