The addition of perfluorobutyl iodide to carbon-carbon multiple bonds and the preparation of perfluorobutylalkenes

Modular and Processable Fluoropolymers Prepared via a Safe, Mild, Iodo–Ene Polymerization

“…Inspired by reports of sodium dithionate (Na 2 S 2 O 4 ) initiated addition of perfluoroalkyl iodides into alkenes, 47 we looked to employ these conditions for the polymerization of diiodoperfluoroalkanes and dienes. We were particularly interested in the brief communication by Rong and Keese, who demonstrated that sonication of perfluorobutyl iodide and 1-hexene in acetonitrile and water gave high yields of iodo–ene product in 1 h. 48 We envisioned that these rapid and mild reaction conditions would enable high-molecular-weight polymers and expand the scope of monomers compatible with the iodo–ene polymerization. Our optimization of the sodium dithionate initiated iodo–ene polymerization began with monomers 1,9-decadiene ( 9 ) and diiodoperfluorohexane ( 10a ) to produce semifluorinated polymer 11a (Scheme 1).…”

A Solid‐Phase Route to 18F‐Labeled Tracers, Exemplified by the Synthesis of [18F]2‐Fluoro‐2‐deoxy‐D‐glucose

“…[21] The yield of this reaction using l6-heptadecenoic acid was lower because of the poor solubility of this olefin. Reaction of acrylic acid with iodide 25 provided the reduced product 29 directly, whilst radical coupling products 26-28 required de-iodination using zinc powder in refluxing Et 2 O/AcOH.…”

Applications of Ultrasound in the Synthesis of organofluorine compounds

“…However, alkenes react with perfluoroalkyl iodides in the presence of Na2S204 [46]. Under sonication in acetonitrile/water [45] as solvent, the addition proceeds in 60-95% yield ( Table 6). The yields are only low with THE Thus, cyclohexene and perfluorobutyl iodide afford the addition product in only 9% yield.…”

“…Cross coupling reactions between aryl iodides and per-Auoroalkyl iodides ( Table 6) proceed smoothly with zinc activated by palladium complexes (e.g. Pd(PPh3)2C12) Table 6 Perfluoroalkylation of alkenes and alkynes with n-C4F9I in the presence of Na2S204 [45] alkene or alkyne product yield [%] )))a' db)…”