A method for synthesizing tetraaryl-substituted vinyl derivatives with electron-deficient groups
An ethylene derivative and electron-deficient technology, which is applied in the field of synthesizing tetraaryl-substituted ethylene derivatives with electron-deficient groups, can solve problems such as expensive catalysts, and achieve the effects of single product, easy separation and simple synthesis method.
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Embodiment 1
[0021] Embodiment 1: the preparation of tetrakis (2-pyridine) ethylene
[0022]
[0023] Add bis(2-pyridyl)methane (142 mg, 0.83 mmol), anhydrous copper acetate (377 mg, 2.08 mmol), potassium carbonate (287 mg, 2.08 mmol) and anhydrous N,N-Dimethylacetamide (14mL) and 18-crown-6 (44mg, 0.17mmol), the reaction mixture was stirred at 120°C for 12h under a nitrogen atmosphere, after the reaction mixture was cooled, the solvent was removed by an oil pump, and the mixture was poured into Ethylenediamine aqueous solution (150 mL, 1M) was added, and the aqueous phase was extracted three times with dichloromethane (50 mL each time). The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed in vacuo, followed by column chromatography to obtain tetrakis(2-pyridyl)ethene (105 mg) with a yield of 75%. 1 H NMR (400 MHz, Chloroform-d) δ 8.50 (ddd, J = 4.9, 1.8, 1.0 Hz, 1H), 7.42 (td, J = 7.7, 1.9 Hz, 1H), 7.10 (dt, J = 7.9,1.1 Hz, 1H), 7.09 – 7...
Embodiment 2
[0024] Embodiment 2: the preparation of tetrakis (4-cyanophenyl) ethene
[0025]
[0026] In a dry Schlenck tube, bis(4-cyanophenyl)methane (65 mg, 0.3 mmol), anhydrous copper acetate (136 mg, 0.75 mmol), potassium phosphate (150 mg, 0.75 mmol) and 18-Crown-6 (16mg, 0.06mmol), then added anhydrous N,N-dimethylacetamide (5 mL) under nitrogen atmosphere and heated for 12 hours with the tube locked. After the reaction mixture was cooled, 50 mL of dilute hydrochloric acid (3 M) was added, the aqueous phase was extracted three times with ethyl acetate (50 mL), and the combined organic phases were washed once with saturated sodium carbonate and saturated brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed in vacuo, and separated by silica gel column chromatography to obtain 62 mg of tetrakis (4-cyanophenyl) ethylene with a yield of 96%. 1 H NMR (400 MHz, Chloroform-d) δ 7.46 (d, J = 8.2 Hz, 1H), 7.07 (d, 8.2H).
Embodiment 3
[0027] Embodiment 3: Preparation of tetrakis (4-pyridyl) ethylene
[0028]
[0029] In a dry three-necked flask, bis(4-pyridyl)methane (5.1 g), anhydrous copper acetate (13.6 g, 75 mmol), and potassium tert-butoxide (8.4 g, 75 mmol, 2.5 eq) were added in one portion. , 18-crown-6 (1.3 g, 6 mmol), followed by the addition of anhydrous hexamethylphosphoric triamide (150 mL, dried over calcium hydride and stored in 4A molecular sieves) under a nitrogen atmosphere. 2 Heated to 120°C under atmosphere and stirred for 12 hours. After the reaction mixture was cooled, the solvent was removed by an oil pump. After adding concentrated ammonia water and dichloromethane in the middle of the reaction mixture, the mixture was transferred to a separatory funnel to separate and remove the water phase, and the organic phase was washed with water twice. After three times, it was dried with anhydrous sodium sulfate, filtered, concentrated in vacuo and separated by column chromatography to obta...
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