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Copper-catalyzed oxidative coupling of diphenylmethanimine promoted by some monodentate pyridines*1

1976; Elsevier BV; Volume: 41; Issue: 3 Linguagem: Inglês

10.1016/0021-9517(76)90237-2

1090-2694

H. Hayashi,

Catalytic C–H Functionalization Methods

Aerial oxidation of diphenylmethanimine to benzophenone azine was carried out at room temperature in the presence of cuprous chloride and a monodentate pyridine, such as pyridine, γ-picoline, isoquinoline, or quinoline. Cupric chloride, hydroxide, and nitrate were inactive in the reaction, whereas CuCl2KOH and Cu(OH)2HCl were active in the presence of excess pyridine. Bidentate ligands, such as ethylenediamine and monoethanolamine, inhibited the oxidative coupling of imine. Using isoquinoline for the direct synthesis of azine from benzophenone, ammonia and molecular oxygen, the reaction temperature can be lowered and the catalysts recycled.