Synthesis of Complex Organofluorine Compounds

Synthesis of SF5-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes

“…On the other hand, the reaction with 1-nitro-3-trifluoromethylbenzene ( 5 ) provided the benzisoxazole product in good yield. This observation is surprising given the fact that the CF 3 and SF 5 groups have similar group electronegativities [14], and the steric difference should not play a role here. These results indicate that the reaction scope shows limitations and the electronic properties of the starting substrates have to be finely tuned for efficient reaction.…”

“…These derivatives are promising for various applications due to an unusual combination of the properties of the SF 5 group, such as high lipophilicity, with strong electron-acceptor character. One important property of the SF 5 group is its high thermal and chemical stability [14–17]. The main reason that prevents further development of SF 5 organics is their limited availability.…”

Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner–Wadsworth–Emmons reaction

“…Less-hindered intermediates A and A’ , which eliminate to E -alkene, exist in equilibrium with more-hindered intermediates B and B’ giving Z -alkene (Scheme 2). In our reactions, the stabilization of the negative charge in the deprotonated phosphonate is higher for 4 than for 3 due to conjugation of the negative charge with the SF 5 group in the former case (σ I (SF 5 ) = 0.55, σ R (SF 5 ) = 0.11 [5]). Consequently, 4 − is more stable and less nucleophilic than 3 − , and therefore, in comparison to the A -to- B equilibrium the A’ -to- B’ equilibrium is shifted more towards A’ providing only ( E ) - 6 product (Scheme 2).…”

N-(2-Tetrafluoro(trifluoromethyl)-λ6-sulfanyl(CF3SF4)-ethyl) Amines: The Influence of the CF3SF4 Group on Lipophilicity and pKa

“…CF 3 and SF 5 substitution is frequently employed in medicinal chemistry to improve the stability of parent compounds in addition to the previous effects . Compared to the CF 3 group, SF 5 has been described as a “super trifluoromethyl” group . Containing additional fluorines, the relatively easily introduced CF 3 SF 4 group is predicted to find utility in both medicinal and materials chemistry.…”