Novel method for using Carbene coupling reaction of palladium-catalyzed sulfur ylide and bromide to synthesize trisubstituted olefin
A sulfur ylide and bromide technology, which is applied in the preparation of organic compounds, organic chemistry, chemical instruments and methods, etc., can solve the problems of explosive diazo compounds and carbene precursor instability, etc., and achieve broad application prospects and easy raw materials. Obtained, the raw material is stable and the effect
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment example 1
[0020] Implementation Case 1: Synthesis of Compound 1
[0021]
[0022] (1) Under argon atmosphere, α-phenyl-α'-ethoxycarbonylthio ylide (24 mg, 0.1 mmol), benzyl bromide (25.4 mg, 0.15 mmol), palladium acetate ( 0.6 mg, 0.0025 mmol), tris(2-furyl)phosphine (0.58 mg, 0.0025 mmol) and lithium tert-butoxide (16 mg, 0.2 mmol), triethylamine (5.0 mg, 0.05 mmol), toluene (1 ml ), placed in an 80°C oil bath and stirred for 24h.
[0023] (2) After the reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain a colorless liquid with a yield of 87%. 1 H NMR (400 MHz, Chloroform- d ) δ 7.84 (s, 1H), 7.41 – 7.33 (m, 3H),7.25 – 7.13 (m, 5H), 7.08 – 7.03 (m, 2H), 4.28 (q, J = 7.1 Hz, 2H), 1.30 (t, J = 7.1 Hz, 3H); 13 C NMR (101 MHz, Chloroform- d ) δ 167.94, 140.20, 136.07, 134.87, 133.02, 130.68, 129.94, 129.05, 128.67, 128.29, 127.86, 61.30, 14.41. HRMS (ESI): m / z Calculated value C 17 h 17 o 2 + :...
Embodiment example 2
[0024] Implementation Case 2: Synthesis of Compound 2
[0025]
[0026] (1) Under argon atmosphere, α-p-tolyl-α'-ethoxycarbonylthio ylide (25.4 mg, 0.1 mmol), benzyl bromide (25.4 mg, 0.15 mmol), bis( Dibenzylideneacetone)palladium(0) (1.43 mg, 0.0025 mmol), 2-dicyclohexylphospho-2,4,6-triisopropylbiphenyl (2.38 mg, 0.005 mmol) and lithium tert-butoxide ( 16mg, 0.2 mmol), triethylamine (5.0 mg, 0.05 mmol), toluene (1 ml), placed in an 80°C oil bath and stirred for 24h.
[0027] (2) After the reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain a colorless liquid with a yield of 64%. 1 H NMR (400 MHz, Chloroform- d ) δ 7.80 (s, 1H), 7.22 – 7.13 (m, 5H),7.12 – 7.04 (m, 4H), 4.26 (q, J = 7.1 Hz, 2H), 2.38 (s, 3H), 1.30 (t, J = 7.1Hz, 3H); 13 C NMR (101 MHz, Chloroform- d ) δ 168.18, 139.95, 137.59, 135.03, 132.96, 132.94, 130.68, 129.79, 129.45, 128.97, 128.28, 61.29, 21.51, 14.44. HRMS (ES...
Embodiment example 3
[0028] Implementation Case 3: Synthesis of Compound 3
[0029]
[0030] (1) Under argon atmosphere, add α-p-tolyl-α'-isobutoxycarbonylthio ylide (26.8 mg, 0.1 mmol), benzyl bromide (25.4 mg, 0.15 mmol), acetic acid Palladium (0.6 mg, 0.0025 mmol), tris(2-furyl)phosphine (0.58 mg, 0.0025 mmol) and potassium carbonate (27.6 mg, 0.2 mmol), triethylamine (5.0 mg, 0.05 mmol), toluene (1 ml ), placed in an 80°C oil bath and stirred for 24h.
[0031] (2) After the reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain a colorless liquid with a yield of 65%. 1 H NMR (400 MHz, Chloroform- d) δ 7.84 (s, 1H), 7.42 – 7.28 (m, 4H),7.23 – 7.10 (m, 4H), 7.05 (d, J = 7.0 Hz, 2H), 3.98 (d, J = 6.4 Hz, 2H), 1.99– 1.86 (m, 1H), 0.88 (d, J = 6.8 Hz, 6H); 13 C NMR (101 MHz, Chloroform- d ) δ167.96, 140.18, 136.14, 134.80, 133.00, 130.72, 129.83, 129.08, 128.63,128.29, 127.79, 71.31, 27.90, 19.18. HRMS (ESI):...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More