A method for the preparation of arylamines by semiconductor photocatalytic c-h activation
A photocatalysis, C-H technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., to achieve the effects of mild conditions, simple and easy-to-obtain catalysts, and safe operation
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Embodiment 1
[0024] In the reactor, add 100 mg of naphthalene, 20 mg of boron-nitrogen-carbon photocatalyst, 100 mg of ammonium chloride as the source of amine groups, 3ml of acetonitrile and 1.2 equivalents of potassium carbonate (adjust the pH value of the initial reaction solution to 8-10), Stir the reaction under light in an oxygen atmosphere at room temperature for 48 hours. After the reaction, extract with ethyl acetate, combine the organic phases to dry, filter, and concentrate under reduced pressure to obtain the crude product. The eluent used in column chromatography is 20:1 volume ratio Petroleum ether: ethyl acetate mixed solvent, yield 53%.
[0025] product:
[0026] Naphthalen-1-amine
[0027] Colorless oil, 15.2 mg, 53% yield. 1 H NMR (400 MHz, CDCl 3 ) δ = 7.83(s, 2H), 7.48 (s, 2H), 7.30 (dd, J =17.9, 10.2, 2H), 6.80 (d, J =6.2, 1H), 4.06(s, 2H). 13 C NMR (101 MHz, CDCl 3 ) δ = 142.08, 134.39, 128.58, 126.37, 125.89, 124.90, 123.65, 120.82, 119.01, 109.72. MS: 143. ...
Embodiment 2
[0029] In the reactor, add 100 mg anisole, 20 mg boron-nitrogen-carbon photocatalyst, 100 mg ammonium chloride as the source of amine groups, 3 ml of dichloroethane and 1.2 equivalents of cesium fluoride (regulate the pH value of the initial reaction solution 8-10), in an oxygen atmosphere and at room temperature, the reaction was stirred under light for 48h, after the reaction was completed, it was extracted with ethyl acetate, the combined organic phase was dried, filtered, concentrated under reduced pressure to obtain the crude product, and the column chromatography eluent used was volume The ratio of petroleum ether: ethyl acetate mixed solvent is 20:1, and the yield is 41%.
[0030] product:
[0031] 4-Methoxyaniline and 2-methoxyaniline
[0032] Colorless oil, 10.1 mg, 41% yield. 1 H NMR (400 MHz, CDCl 3 ) δ = 6.82 –6.71 (m, 2H), 6.66 (d, J =8.2, 2H), 3.85 (s, 1H), 3.45 (N-H, 2H). 1 H NMR (400MHz, CDCl 3 )δ = 6.82 – 6.71 (m, 2H), 6.66 (d, J =8.2, 2H), 3.75 (s, 3...
Embodiment 3
[0034] In the reactor, add 100 mg 1,3,5-trimethoxybenzene, 20 mg boron nitrogen carbon photocatalyst, 100 mg ammonium chloride as the amine source, 3ml dimethyl sulfoxide and 1.2 equivalents of cesium fluoride (Regulate the pH value of the initial reaction solution to be 8-10), stir the reaction in an oxygen atmosphere at room temperature for 48 hours, extract with ethyl acetate after the reaction, combine the organic phases to dry, filter, and concentrate under reduced pressure to obtain the crude product. The chromatographic eluent was petroleum ether: ethyl acetate mixed solvent with a volume ratio of 10:1, and the yield was 41%.
[0035] product:
[0036] 2,4,6-Trimethoxyaniline
[0037] Colorless oil, 15.0 mg, 41% yield. 1 H NMR (400 MHz, CDCl 3 ) δ 6.18 (d, J = 1.7 Hz, 2H), 3.83 (s, 6H), 3.76 (s, 3H), 3.27 (s, 2H). 13 C NMR (101 MHz, CDCl 3 ) δ = 152.58, 148.08, 118.97, 91.48, 55.86.
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