Synthesis and fluorophilicity of compounds with tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl substituent

Imidazolium Based Fluorous N‐Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification

“…Unsymmetrically substituted imidazolium salts containing fluorous moiety and methyl or isopropyl substituent were prepared analogously to recently described butyl derivative . As shown in Scheme , this procedure involved quaternization of imidazoles with silicon‐branched fluorous tag containing iodopropyl group.…”

“…In the course of our ongoing studies focused on tagging of organic and organometallic compounds by fluorous chains we have recently synthesized a new type of fluorinated imidazolium ionic liquid . Here we report the synthesis, properties and catalytic activity of several new organocatalysts bearing large fluorous substituent in the redox esterification of cinnamaldehyde, together with a suitable recycling procedure, which is, in contrast to recyclable polymer supported catalyst systems, based on a unique behavior of highly fluorinated substances .…”

Synthesis of novel fluorous pyridinium ionic liquids

“…Next, the addition of silylpropyl iodide having three perfluoroalkyl groups on the silicon atom to nitrogen atom of pyridine derivatives was explored to yield pyridinium ionic liquids possessing much more fluorous alkyl groups. Strasák et al [5a]. have reported the synthesis of highly fluorous imidazolium ionic liquids by using fluorous ponytail such a tris(3,3,4,4,5,5,6,6,7,7,8,8,8‐tridecafluorooctyl)silyl substituent.…”

“…have reported the synthesis of highly fluorous imidazolium ionic liquids by using fluorous ponytail such a tris(3,3,4,4,5,5,6,6,7,7,8,8,8‐tridecafluorooctyl)silyl substituent. The tris(tridecafluorooctyl)silylpropyl iodide was prepared as reported in literature [5a,12]. Then the reaction of pyridine derivatives with the obtained silylpropyl iodide resulted in the formation of the corresponding pyridinium iodides.…”

“…Recently, we have reported an efficient synthesis of highly fluorous aliphatic ammonium ionic liquids having perfluoroalkyl groups on anion and/or cation moieties [4]. On the other hand, the highly fluorinated aromatic ammonium salts have already been reported,[5-7] but there are few reports about perfluoroalkylated aromatic ionic liquids having highly fluorous properties [5]. In practice, many highly fluorinated salts did not show high fluorophilicity or not clarified the fluorophilicity,[6] or they were high temperature‐melting solids [7]…”