Incorporation of the pentafluorosulfanyl group through common synthetic transformations

The incorporation of –SF 5 group onto model amino acids has been achieved using commercially available synthons substituted with this group. This work investigates the influence of the –SF 5 group on a variety of common synthetic transformations utilized in fields of bioconjugation and drug development, namely, amide coupling, reductive amination, diazo-coupling, and CuAAC “click” reactions. The influence of the novel substituent on the success of these common transformations is presented, and alternative approaches for those which proved unsatisfactory are proposed herein. Graphic abstract