Oxidative Coupling Of 2-Naphthol Derivatives Catalyzed By The Imidazoles -Cu(Ⅰ) Complexes

Binaphthol and its derivatives have been extensively used in theasymmetric synthesis, molecular recognise and new materials.Exploration of high effective catalyst which oxidative coupling of2-naphthol to binaphthol is a highlight in modern synthetic chemistry. Inthis paper, we reported a novel and effective aerobic oxidative couplingsystem of N-alkylimidazole-Cu(Ⅰ) complexes. Then we applied thesecatalytic system to oxidative coupling 2-naphthol and its derivatives,good yields were achieved. Among these catalytic system of N-alkylimidazole-Cu(Ⅰ or Ⅱ )complexes, the N-methylimidazole-CuCl complex is the best catalyst.The yield of oxidative coupling 2-naphthol to binaphthol is up to 90% in0 ℃ , 88% in room temperature. The yields of oxidative coupling3-hydroxy-2-naphthoic acid ester to the corresponding binaphthalene areup to 99% in room temperature. In the experiment, we obtained the crystal structure ofN-methylimidazole-CuCl2 · 2H2O complex. The crystal structure wasconfirmed by X-ray analysis. According to the achieved data, weinvestigated the catalytic oxidative process and supposed a mechanism ofthe oxidative reaction. i陈丽 四川大学硕士学位论文 2004 年 In this paper, we synthesized the (S)-diphenyl(α-pyrrolidyl)methanol and applied the (S)-diphenyl(α-pyrrolidyl)methanol-CuClcomplex as chiral catalyst to asymmetric oxidative coupling of2-naphthol and its derivatives. The ee values were up to 50.4%, theyield were up to 44%.