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An Unconventional Mechanistic Insight into SCF3 Formation from Difluorocarbene: Preparation of 18 F-Labeled ?-SCF3 Carbonyl Compounds.

ABSTRACT: Trifluoromethylthiolation by sulfuration of difluorocarbene with elemental sulfur is described for the first time, which overrides long-standing trifluoromethyl anion-based theory. Mechanistic elucidation reveals an unprecedented chemical process for the formation of thiocarbonyl fluoride and also enables transition-metal-mediated trifluoromethylthiolation and [18 F]trifluoromethylthiolation of ?-bromo carbonyl compounds with broad substrate scope and compatibility.

SUBMITTER: Zheng J 

PROVIDER: S-EPMC5582945 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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An Unconventional Mechanistic Insight into SCF<sub>3</sub> Formation from Difluorocarbene: Preparation of <sup>18</sup> F-Labeled α-SCF<sub>3</sub> Carbonyl Compounds.

Zheng Jian J   Cheng Ran R   Lin Jin-Hong JH   Yu Dong-Hai DH   Ma Longle L   Jia Lina L   Zhang Lan L   Wang Lu L   Xiao Ji-Chang JC   Liang Steven H SH  

Angewandte Chemie (International ed. in English) 20170214 12

Trifluoromethylthiolation by sulfuration of difluorocarbene with elemental sulfur is described for the first time, which overrides long-standing trifluoromethyl anion-based theory. Mechanistic elucidation reveals an unprecedented chemical process for the formation of thiocarbonyl fluoride and also enables transition-metal-mediated trifluoromethylthiolation and [<sup>18</sup> F]trifluoromethylthiolation of α-bromo carbonyl compounds with broad substrate scope and compatibility. ...[more]

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