Chiral organic, inorganic polymer assembled catalyst, synthesis method and use
A technology of catalysts and compounds, which is applied in a class of chiral organic-inorganic polymer assembly catalysts, synthesis and applications, and can solve the problems of complex synthesis of polymer ligands and low loading of catalytically active species
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Embodiment 1
[0073] Example 1: In a dry 25mL standard Schlenk bottle, under argon protection, compound 7a (0.57g), hexamethylphosphinetriamine (0.46mL), and anhydrous toluene (5mL) were added, stirred and heated to reflux for 9h, Heating was stopped and cooled to room temperature, the solvent was evaporated under reduced pressure, and column chromatography (n-hexane:ethyl acetate=10:1) gave a white foamy solid, which was recrystallized from ether to give compound 8a (0.6g). 83.5% yield.[α] D 20=650.1°(c 1.0, CHCl3).IR(KBr): 3055, 2800, 1621, 1588, 1504, 1462, 1330, 1293, 1232, 1207, 1189, 1076, 983, 944, 821, 780, 749, 692 , 678 cm-1.1H NMR (300MHz, CDCl3): δ8.24-8.26 (m, 2H), 7.94-8.08 (m, 6H), 7.64-7.71 (m, 2H), 7.39-7.58 (m, 10H) , 7.29-7.37 (m, 2H), 2.58-2.62 (m, 12H).31P NMR (121MHz, CDCl3) δ149.87 ppm. MS (ESI): (M+H), 717.35; HRMS (MALDI): calcd .forC44H35N2O4P2: 717.2072; Found: 717.2053.
Embodiment 2
[0074] Example 2: In a dry 25mL standard Schlenk bottle, under argon protection, compound 7b (0.65g), hexamethylphosphinetriamine (0.46mL) and anhydrous toluene (5mL) were added, stirred and heated to reflux for 12h, Heating was stopped and cooled to room temperature, the solvent was evaporated under reduced pressure, and column chromatography (n-hexane: ethyl acetate = 10:1) gave a white foamy solid, which was recrystallized from ether to give compound 8b (0.62 g). 78.5% yield.[α] D 20 =500.6° (c 1.0, CHCl 3 ).IR(KBr): 3054, 2799, 1590, 1494, 1464, 1333, 1292, 1232, 1208, 1047, 984, 945, 819, 790, 749, 693cm -1.1 H NMR (300MHz, CDCl 3 ): δ8.18(s, 2H), 7.91-8.06(m, 6H), 7.82(s, 4H), 7.26-7.62(m, 14H), 2.55-2.59(m, 12H). 31 P NMR (121MHz, CDCl 3 )δ149.87ppm. MS (ESI): (M+H), 793.55; HRMS (MALDI): calcd.for C 50 h 39 N 2 o 4 P 2 : 793.2385; Found: 793.2379.
Embodiment 3
[0075] Example 3: In a dry 25mL standard Schlenk bottle, under argon protection, compound 7c (0.65g), hexamethylphosphinetriamine (0.46mL), anhydrous toluene (5mL) were added, stirred and heated to reflux for 12h, Heating was stopped and cooled to room temperature, the solvent was evaporated under reduced pressure, and column chromatography (n-hexane:ethyl acetate=10:1) gave a white foamy solid, which was recrystallized from ether to give compound 8c (0.67g). 85.0% yield.[α] D 20 =485.0°(c 1.0, CHCl 3 ).IR (KBr): 3054, 2799, 1621, 1588, 1505, 1463, 1332, 1292, 1232, 1207, 1188, 1155, 1075, 984, 945, 884, 820, 796, 749, 693cm -1.1 HNMR (300MHz, CDCl 3 ): 8.18-8.19(m, 2H), 7.91-8.05(m, 7H), 7.69-7.71(m, 2H), 7.41-7.65(m, 13H), 7.29-7.34(m, 2H), 2.55-2.59 (m, 12H). 31 P NMR (121MHz, CDCl 3 )δ149.48 ppm. MS (ESI): (M+H), 793.35; HRMS (MALDI): calcd.forC 50 h 39 N 2 o 4 P 2 : 793.2385; Found: 793.2379.
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