Synthesis of 2‐(Pentafluoro‐λ⁶‐sulfanyl)acetamides and Impact of the Fluorinated Group on the Lipophilicity

Abstract The synthesis of 2‐(pentafluoro‐λ 6 ‐sulfanyl)acetamides is described via an amidation reaction between 2‐(pentafluoro‐λ 6 ‐sulfanyl)acetic acid, the SF 5 ‐containing building block, and various amines. A total of 27 examples of SF 5 ‐containing amides were synthesized, with isolated yields going from 43 % to quantitative. We showed that a 2‐(pentafluoro‐λ 6 ‐sulfanyl)acetamide could be converted to a N ‐(2‐SF 5 ‐ethyl)amine and a SF 5 ‐containing oxadiazoles. Finally, the effect of the SF 5 substituent on the lipophilicity of the amide of a model compound was evaluated.