A kind of phosphine ligand of benzimidazole-indole skeleton and its preparation method and application
A technology of benzimidazole and phosphine ligands is applied in the field of organic compounds and synthesis, which can solve the problems of high catalytic activity, low dosage of transition metal catalysts, can not meet the requirements of easy preparation and the like, and achieves good selectivity, simple method, and changes in coordination. performance effect
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[0029] And, the embodiment of the present invention also provides a 2-(3-(disubstituted phosphino)-N-alkyl-1H-indol-2-yl)-N-alkyl-benzimidazole skeleton phosphine complex The preparation method of body, comprises the following steps:
[0030] S01. Dissolve indole-2-carboxylic acid, o-phenylenediamine and sulfuric acid in ethylene glycol, and stir for 2-36 hours under heating and reflux to obtain (1H-indol-2-yl)-1H- Benzo[d]imidazole intermediate;
[0031] S02. Dissolve the (1H-indol-2-yl)-1H-benzo[d]imidazole intermediate, sodium hydride or potassium hydroxide in tetrahydrofuran or dimethylformamide at 0°C or room temperature Stir at room temperature for 0.5-2 hours, then add dimethyl sulfate or alkyl bromide or alkyl tosylate, and stir at room temperature for 2-36 hours to obtain 2-(N-alkyl-1H-indol-2-yl )-N-alkyl-benzimidazole;
[0032] S03. Dissolve the 2-(N-alkyl-1H-indol-2-yl)-N-alkyl-benzimidazole in tetrahydrofuran, and add N-bromosuccinyl at a temperature of 0°C Am...
Embodiment 1
[0054] An indole imidazolyl phosphorus ligand, its structure is 2-(3-(diphenylphosphino)-1-methyl-1H-indol-2-yl)-N-methyl-benzene And imidazole,
[0055]
[0056] The preparation method of the 2-(3-(diphenylphosphino)-1-methyl-1H-indol-2-yl)-N-methyl-benzimidazole is:
[0057] In a 500 ml round bottom flask, add 8.30 g of indole-2-carboxylic acid (52 mmol), then add 5.40 g of o-phenylenediamine (50 mmol), slowly add 50 ml of ethylene glycol, and heat slowly until the reactant is completely dissolved , and then slowly add 2.8 ml of sulfuric acid (53 mmol) at room temperature, and heat to reflux for 2-36 hours. The mixture was poured into ice water to terminate the reaction, then 100 ml of ammonium hydroxide was added to the system to neutralize the pH value, and then 150 ml of ether was added for three times for extraction and separation. The organic phases were combined and dried over anhydrous magnesium sulfate. After the organic phase was concentrated, 10.0 g of brown ...
Embodiment 2
[0062] An indole imidazolyl phosphorus ligand, its structure is 2-(3-(diphenylphosphino)-1-ethyl-1H-indol-2-yl)-N-ethyl-benzene And imidazole,
[0063]
[0064] The preparation method of the 2-(3-(diphenylphosphino)-1-ethyl-1H-indol-2-yl)-N-ethyl-benzimidazole is:
[0065] In a 100 ml three-neck flask pumped by nitrogen, weigh 3.96 g of (1H-indol-2-yl)-1H-benzo[d]imidazole (17 mmol), add 70 ml of dimethylformamide, and stir well . Then add 5.63 grams of potassium hydroxide (100mmol) and stir completely at room temperature to react evenly for 2-36 hours. Along with most of the potassium hydroxide dissolves, a thick and turbid solution is formed. Add 5.0 milliliters of ethyl bromide (67mmol), React at room temperature for 18-24 hours. Spot plate monitoring, when the reaction of the raw materials is complete, stop the reaction, add 70 ml of water and 40 ml of dichloromethane to the system, then add 40 ml of dichloromethane for three times for extraction, combine the organic...
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