Simple method for synthesizing polysubstituted arylketone compound under catalysis of palladium metal
A metal catalysis and synthesis method technology, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of increased reaction difficulty, narrow substrate range, harsh reaction conditions, etc., and achieves low cost and stable properties. , the effect of mild reaction conditions
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Embodiment 1
[0032] Embodiment 1, (E)-3-(2-benzoyl-6-methylphenyl) butyl acrylate ( image 3 ).
[0033] In the 25ml Schlenk reaction tube, add reactant 2a (0.8mmol), catalyst [PdCl(C 3 h 5 )] 2 (2.5mol%), ligand TFP (10 mol%), base Cs 2 CO 3 (0.6 mmol), evacuate and change nitrogen three times, then reactant 1a (0.2mmol, 1.0 equiv.), reactant 3a (1.5 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2 mL) was added, and the reaction was at 90 o C for 10 hours. The progress of the reaction was monitored by TLC. After the reaction was completed, silica gel was directly added, spin-dried and subjected to column chromatography to obtain pure target product 4a (53.5 mg, 83%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.30-7.69 (m, 3H), 7.54 (t, J = 7.2 Hz, 1H), 7.40 (t, J = 7.6 Hz,2H), 7.34 (t, J = 7.2 Hz, 2H), 7.27 (d, J = 6.8 Hz, 1H), 5.88 (d, J = 16 Hz,1H), 4.06 (t, J = 6.4 Hz, 2H), 2.42 (s, 3H), 1.61-1.53 (m, 2H), 1.37-1.27 (m,2H), 0.91 (t, J = 7.6Hz, 3H). ...
Embodiment 2
[0034] Embodiment 2, (E)-3-(2-benzoyl-6-methylphenyl) butyl acrylate ( Figure 4 ).
[0035] In the 25ml Schlenk reaction tube, add reactant 2a (0.8mmol), catalyst Pd(OAc) 2 (5 mol%), ligand TFP (10 mol%), base Cs 2 CO 3 (0.6 mmol), vacuum three times for nitrogen, then reactant 1a (0.2 mmol, 1.0equiv.), reactant 3a (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL) was added, and the reaction was at 90 o C for 10 hours. The progress of the reaction was monitored by TLC. After the reaction was completed, silica gel was directly added, spin-dried and subjected to column chromatography to obtain pure target product 4a (50.2 mg, 78%). Analysis data is with embodiment 1.
Embodiment 3
[0036] Embodiment 3, (E)-3-(2-benzoyl-6-isopropylphenyl) butyl acrylate ( Figure 5 ).
[0037] In the 25ml Schlenk reaction tube, add reactant 2a (0.8mmol), catalyst [PdCl(C3 h 5 )] 2 (2.5mol%), ligand TFP (10 mol%), base Cs 2 CO 3 (0.6 mmol), evacuated and changed nitrogen three times, then reactant 1b (0.2mmol, 1.0 equiv.), reactant 3a (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2 mL) was added, and the reaction was at 90 o C for 10 hours. The progress of the reaction was monitored by TLC. After the reaction was completed, silica gel was directly added, spin-dried and subjected to column chromatography to obtain pure target product 4b (63%). 1 H NMR (400 MHz, CDCl 3 ): δ7.740 (d, J = 16 Hz, 1H), 7.62 (d, J = 7.6 Hz, 2H), 7.46 (t, J = 7.6 Hz, 1H), 7.40 (d, J = 7.6 Hz, 1H), 7.34 (q, J = 6.8 Hz, 3H), 7.20 (d, J = 7.6 Hz, 1H), 5.75 (d, J = 16.4 Hz, 1H), 3.98 (t, J = 6.8 Hz, 2H), 3.15-3.08 (m, 1H), 1.53-1.46 (m, 2H), 1.29...
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