Highly efficient trifluoromethylation and [18F]trifluoromethylation


Jichang Xiao, researcher at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, has created a new trifluoromethylthiolation method to achieve high-efficiency trifluoromethylation of aliphatic electrophilic compounds with difluorocarbene, elemental sulfur, and fluoride anions reaction. This reaction has two distinct advantages: rapid reaction, the reaction can be completed within 5 minutes; the construction of trifluoromethylthio group is no longer required to use CF3- or CF3S-reagents as in the conventional method, but the combination of sulfur and fluorine anion with difluorocarbene. Thanks to these outstanding advantages, this reaction can be effectively applied to the 18F-labeled trifluoromethylation reaction.


Dr. Liang Huan from Harvard Medical School, verified the idea of [18F]trifluoromethylation reaction and found that the reaction is easy to achieve 18F-labeling, and the construction of [18F]CF3S was realized for the first time. Similarly, the reaction proceeds quite rapidly (less than 1 minute) and is very simple to operate, meeting the synthesis requirements of 18F-labeled molecules. It is worth mentioning that the reaction does not require the participation of transition metals, reducing the risk of injecting toxic metals into the body. It can be seen that this strategy has great application prospects in the synthesis of [18F]CF3S-labeled drugs and subsequent PET studies.


This result is published in "Angew. Chem. Int. Ed."