Quantification of the Activation Capabilities of Lewis/Bronsted Acid for Electrophilic Trifluoromethylthiolating Reagents

The Summary of main observation and conclusion Electrophilic trifluoromethylthiolation has emerged as an important and efficient methodology for installing the SCF3 moiety onto an array of organic molecules. Due to the low reactivities of trifluoromethylthiolating reagents, these transformations often require activation through an exogenous Lewis/Bronsted acid. We report herein the quantification of the activation capabilities of Lewis/Bronsted acids for trifluoromethylthiolating reagents through computing the difference in trifluoromethylthio cation donor ability (Tt(+)DA) between the activated and unactivated reagent. A moderate correlation is found to exist between the activation capability and Lewis acidity.