Polyfluoroalkoxylation reactions. Mechanistic studies on the peculiar behavior of polyfluoroalcohols as nucleophiles(Abstracts)

摘要

Considerable time and attention have been and continue to be directed toward the synthesis of highly fluorinated organic materials, due to the interesting properties they show by the presence of a large amount of fluorine atoms in their structures . Moreover, the interest for this type of compounds has increased by the demonstrated usefulness of polyfluorinated polymers, biphasic fluorinated chemistry, and their ability to stabilize metal nanoparticles. These new nanoparticulated materials can be used as easily recovered and reused catalyst for organic reactions in homogeneous and biphasic media. Preparation of polyfluoroalkoxyaromatics has been reported following two main approaches: i) the reactions of electrophilic haloalkyl fluorides, fluoroalkenes, or fluoroalkylsulfonates with nucleophilic phenol derivatives and ii) direct aromatic nucleophilic substitution reactions between polyfluoroalkoxyde anions and chloro-, fluoro-, or nitro-substituted electron-poor aromatics in dipolar aprotic solvents. However, no general and mild conditions had, previously to our work, been reported.