The trifluoromethylthio fragment was successfully incorporated into both primary (Scheme 2, entries 43 and 44) and secondary alkyl electrophiles (Scheme 2, entries 45 and 46), obtaining natural product derivatives such as SCF3-modified methionine, cholesterol and androsterone in good to excellent yields (up to 94%). Nucleophilic substitution reactions with benzylic and allylic substrates, including a celecoxib derivative, resulted in trifluoromethythiolated products with excellent yields (Scheme 2, entries 47-49). Notably, these transformations could be efficiently carried out in a telescoped flow fashion resulting in a remarkable reduction of the reaction time from 2 hours to just 5 minutes, while maintaining practically similar yields. The generated anions were also subjected to an aromatic nucleophilic substitution reaction, yielding a Csp 2 -SCF3 product (Scheme 2, entry 50), as well as in a nucleophilic acyl substitution, resulting in the formation of the desired thioesters (Scheme 2, entries 51 and 52).