Application Of Fluorous Multibranched Gemini Ammonium In Organic Reactions

A series of novel Gemini quaternary ammonium compounds with multi-branch perfluoroalkyl and multi-carboxyl have been synthesized from Behera's amine, 1,6-diaminlhexane, and perfluoroalkyl via nucleophilic substitution, quaternization and hydrolysis of tert-butyl. A series of ligand derivatives, which might be possible catalysts, have also been synthesized via neutralization, anion exchange, complexed with rare earth metals. The ligands' solubility, stability and surfactivity have been studied. Thermogravimetry-differential thermal analysis (TG/DTA) of the ligands reveals that the rare earth metal complexes are stable below 195℃. Furthermore, the critical micelle concentration (CMC) values and surface tension values have been tested and the corresponding saturated absorptions and molecule sectional areas have been calculated.The prepared polycarboxylic acid ligands have been utilized to catalyzed aza-Friedel-Crafts reaction, with the advantages of good to excellent results (up to 92% yield), avoiding organic solvent, and recoverable. The Mannich reaction was highly promoted by only 0.1 mol% of six-carboxylic acid sodium of the ligand (up to 90% yield). A highly efficient synthesis of 2,4-disubstituted quinolines catalyzed by the polycarboxylic acid ligands complex with rare earth metals in situ via one-pot reaction of aldehydes, alkynes, and amines has been investigated. The complex can also catalyze Kabacknick-Fields reaction efficiently in water (up to 90% yield). Moreover, the application of polycarboxylic acid ligands and polycarboxylic sodium ligands on dye dispersion have been explored and achieved satisfactory results. Another way, an efficient synthesis of novel four-ring structure of naphthyridine derivatives via Sc(OTf)3-catalyzed domino reaction of methylene amines and 2-aminoacetophenone has been explored, and a possible mechanism also has been proposed.