Introduction of Trifluoromethylthio Group into Organic Molecules

Among many fluoroalkyl groups, the trifluoromethylthio group (–SCF3) has attracted intense interest recently, mainly due to its unique properties that may be beneficial for new drug discovery. More specifically, the trifluoromethylthio group is one of the most lipophilic functional groups that are capable of significantly enhancing the drug molecule's ability to cross the cell membrane. As a result, the pharmacokinetic properties of the drug molecules would be greatly improved and in general, the dosage of drug could be reduced. Secondly, the trifluoromethylthio group is an electron-withdrawing group that can decrease the overall electron density of the drug molecule. Consequently, trifluoromethylthiolated drug molecules are not readily oxidized in vivo, thus significantly improving their metabolic stability.