Study On Suzuki Cross-Coupling Catalytic Reaction And The Design, Synthesis Of Conjugated Compounds Containing 8-Hydroxyquinoline

Many Suzuki Cross-Coupling compound and 8-hydroxyquinoline derivatives are very important intermediates to synthesize medicament.The organic ligand metal complexes with 8-hydroxyquinoline has been applied widely on OLED. Organic ligand metal complexes with 8-hydroxyquinoline has been the ideal organic light-emitting materials. These studies are currently a key focal point of science research. There are two aspects in this thesis, on one hand, ferocenylimidazolines cyclopalladated complexes were used as catalysises in Suzuki cross-coupling and different substituent group boric acids were used as substrates. On the other hand, large conjugated compounds based on 8-Hydroxyquinoline were designed and synthesized.First, valine , L-phenylalanine and ferocene were used as starting materials which were performed reductive reaction , oxidation , protection, cyclization to synthesize ferocenylimidazolines cyclopalladated 91(a-h) and different substituted substrates were used in Suzuki cross-coupling reaction under room temperature in water. The best reaction conditions was gained: methylate and water (2:1)was used as solvent, KOH was added as base, the temperature was room temperature. Under the optimal reaction conditions, Suzuki reaction of different substituent group boric acids was performed efficiently.Second, The target molecular with the unit 8-hydroxyquinoline were designed and synthesized using 2-methyl-quinolin-8-ol, ferrocenecarboxaldehyde and 2,3,6,7-tetramethoxy phenanthrene-9-carbaldehyde as starting materials and two synthetic routs were performed. Method one: 2-methyl-quinolin-8-ol reacted respectively with ferrocenecarboxaldehyde and 2,3,6,7-tetramethoxy phenanthrene-9-carbaldehyde using Perkin-type reaction to yield 8-hydroxyquinoline, ferrocene and phenanthrene Cross-Coupling complexes. As a result, long time and high temperature were favor to the reaction. Second method: in order to gain the wittig reagent in 2-position of 8-hydroxyquinoline, the Blanc reaction was selected which contained the operation of chloromethylation, hydroxylation, halogenations and Alkylidenetriphenylphosphoranes. when the wittig reagent reacted with 2,3,6,7-tetramethoxy phenanthrene-9-carbaldehyde, different solvent conditions were examined and finally afforded the targe molecule of 2- large conjugated substituent 8-hydroxyquinoline complexes. These novel compounds were characterized by IR and NMR spectra.