Ruthenium complex containing carboryl benzimidazole structure and its preparation method and application
A technology containing carboboryl benzimidazole and carboryl benzimidazole is applied in the field of semi-sandwich ruthenium complexes and their preparation, and can solve the problems of environmental impact, high price of iridium complexes, toxic large selenium compounds and the like , to achieve the effects of high stability, high catalytic activity and yield, and simple synthesis process
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Embodiment 1
[0031] Synthesis of half-sandwich ruthenium complexes containing ortho-carboryl benzimidazole structures:
[0032]
[0033] Among them, "·" represents the boron-hydrogen bond B-H.
[0034] At -78°C, n-BuLi (1.6M) in n-hexane (1.00 mL, 1.6 mmol) was slowly added dropwise to the o-C 2 B 10 h 10 (92.0mg, 0.64mmol) in tetrahydrofuran solution, stirred at this temperature for 30 minutes, slowly rose to room temperature and continued to react for 1 hour, then added bromobenzimidazole (126.7mg, 0.64mmol), and continued to react at room temperature for 6 Hour. Then the binuclear ruthenium compound [(p-cymene)RuCl 2 ] 2 (256.0 mg, 0.32 mmol) was added to the reaction system for an additional 3 hours. After the reaction, stand and filter, and dry the solvent under reduced pressure. The crude product obtained is separated by column chromatography (petroleum ether / tetrahydrofuran=6:1) to obtain the orange-red target product ruthenium (II) complex Ru (254.4 mg, Yield 75%).
[00...
Embodiment 2
[0038] Ruthenium(II) complexes catalyze the autoxidative coupling reaction of primary amines:
[0039]
[0040] The ruthenium complex prepared in Example 1 was used as a catalyst to catalyze the autoxidative coupling reaction of primary amines: in benzylamine (1mmol, 107mg), add a compound containing ortho carborane o-C 2 B 10 h 10 The divalent ruthenium complex (0.001mmol, 1.3mg) in toluene (toluene) solution, and pass into air as an oxidant to react, the reaction temperature is 60°C, and the reaction time is 180 minutes. After the end, the concentrated reaction solution is directly passed through the silica gel column Chromatographic separation, drying to constant mass, to obtain the corresponding imine compound C 14 h 13 N (yield 87%), 1 H NMR (400MHz, CDCl 3):δ=8.32(s,1H),7.72-7.69(m,2H),7.35-7.33(d,J=1.8Hz,3H),7.27-7.26(d,J=4.4Hz,4H),7.20- 7.17 (m, 1H), 4.75 (s, 2H), elemental analysis: C 86.12, H 6.71, N 7.17 (theoretical); C 86.06, H 6.68, N 7.12 (actual).
Embodiment 3
[0042] Ruthenium(II) complexes catalyze the autoxidative coupling reaction of primary amines:
[0043]
[0044] The ruthenium complex prepared in Example 1 was used as a catalyst to catalyze the autoxidative coupling reaction of primary amines: in 4-methylbenzylamine (1mmol, 137mg), add an ortho carborane o-C 2 B 10 h 10 Divalent ruthenium complex (0.001mmol, 1.3mg) in toluene solution, and air was introduced as an oxidant to react, the reaction temperature was 80°C, and the reaction time was 60 minutes. After the end, the concentrated reaction solution was directly separated by silica gel column chromatography , dried until the mass remains unchanged, and the corresponding imine compound C 16 h 17 N (yield 96%), 1 H NMR (400MHz, CDCl 3 ):δ=8.38(s,1H),7.70-7.64(d,J=6.8Hz,2H),7.39-7.36(d,J=4.0Hz,2H),7.30-7.18(m,4H),4.75( s, 2H), 2.41 (s, 3H), 2.35 (s, 3H), elemental analysis: C86.05, H 7.67, N 6.27 (theoretical); C 86.14, H 7.65, N 6.32 (actual).
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