Synthesis of ArCF<sub>2</sub>X and [<sup>18</sup>F]Ar-CF<sub>3</sub> via Cleavage of the Trifluoromethylsulfonyl Group
Ren‐Yin Yang, Xinyan Gao, Kehao Gong, Juan Wang, Xiaojun Zeng, Mingwei Wang, Junbin Han, Bo Xu
Abstract
A versatile synthesis of ArCF2X and [18F]Ar-CF3 type compounds from readily available ArCF2SO2CF3 has been developed. Diverse nucleophiles, including weak nucleophiles such as halides (18F–, Cl–, Br–, and I–), RSH, and ROH, could react with ArCF2SO2CF3 efficiently to give the corresponding difluoromethylene products. The control experiments and the Hammett plot indicated that the reaction might proceed through a difluorocarbocation intermediate generated from the steric hindrance-assisted cleavage of the trifluoromethylsulfonyl group.
Topics & Concepts
ChemistryNucleophileSteric effectsCleavage (geology)HalideMedicinal chemistryGroup (periodic table)StereochemistryOrganic chemistryCatalysisGeotechnical engineeringEngineeringFracture (geology)Fluorine in Organic ChemistryInorganic Fluorides and Related Compounds