Difluorocarbene‐Derived Trifluoromethylthiolation and [18F]Trifluoromethylthiolation of Aliphatic Electrophiles |
| |
Authors: | Jian Zheng Lu Wang Jin‐Hong Lin Prof?Dr Ji‐Chang Xiao Prof?Dr Steven H Liang |
| |
Institution: | 1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China);2. Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital & Department of Radiology, Harvard Medical School, 55 Fruit St., White 427, Boston, MA (USA) |
| |
Abstract: | The first trifluoromethylthiolation and 18F]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 18F]CF3S‐labeled molecules from most commonly used 18F]fluoride ions. The rapid radiochemical reaction time (≤1 min) and high functional‐group tolerance allow access to a variety of aliphatic 18F]CF3S compounds in high yields. |
| |
Keywords: | carbenes fluorine isotopic labeling positron emission tomography sulfur |
|
|