Method for catalytically synthesizing alpha-aryl vinyl sulphone by aid of Pd
A technology of aryl vinyl and sulfone, which is applied in the field of Pd-catalyzed synthesis of α-aryl vinyl sulfone, which can solve the problems of limited use and achieve the effects of mild reaction conditions, strong functional group compatibility, and good substrate universality
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Embodiment 1
[0022] Add 0.3mmol of α-bromovinylphenyl sulfone, 0.45mmol of phenylboronic acid, 0.015mmol of palladium acetate, 0.6mmol of cesium carbonate, and 0.03mmol of SPhos into the Schlenk reaction tube (10mL), and cycle three times with vacuum and nitrogen release. Under the protection of nitrogen, add 2.0 mL of anhydrous toluene and stir at 50°C for 15 hours; after TLC confirms that the reaction is complete, use 15.0 mL of ethyl acetate as eluent, and pass through a 2 cm silica gel short column to remove inorganic salts; then the organic phase is rotary evaporated After removing the solvent (namely ethyl acetate and toluene), use the mixture of petroleum ether and ethyl acetate with a volume ratio of 5:1 as eluent for column chromatography separation, and finally obtain α-phenylethylene by rotary evaporator distillation 62.2 mg of phenyl sulfone, and the yield was 85%. The analysis data is as follows:
[0023] 1 HNMR (500MHz, CDCl 3 ):δ5.96(s,1H),6.63(s,1H),7.25-7.28(m,5H),7.39-...
Embodiment 2
[0025] Add 0.3mmol of α-bromovinylphenyl sulfone, 0.45mmol of p-fluorophenylboronic acid, 0.015mmol of palladium acetate, 0.6mmol of cesium carbonate, and 0.03mmol of SPhos into the Schlenk reaction tube (10mL), and vacuumize and release nitrogen for three times. Under the protection of nitrogen, add 2.0 mL of anhydrous toluene and stir at 50°C for 15 hours; after TLC confirms that the reaction is complete, use 15.0 mL of ethyl acetate as eluent, and pass through a 2 cm silica gel short column to remove inorganic salts; then the organic phase is rotary evaporated After removing the solvent, the mixture of petroleum ether and ethyl acetate with a volume ratio of 5:1 was used as the eluent for column chromatography separation, and finally 72.3 mg of α-p-fluorophenylvinylphenyl sulfone was obtained by distillation with a rotary evaporator , the yield was 92%. The analysis data is as follows:
[0026] 1 HNMR (500MHz, CDCl 3 ):δ5.94(s,1H),6.63(s,1H),6.96(t,J=8.7Hz,2H),7.29-7.33(...
Embodiment 3
[0028] Add 0.3mmol of α-bromovinylphenylsulfone, 0.45mmol of 4-methoxycarbonylphenylboronic acid, 0.015mmol of palladium acetate, 0.6mmol of cesium carbonate, and 0.03mmol of SPhos into the Schlenk reaction tube (10mL), and cycle three times with vacuum and nitrogen release . Under the protection of nitrogen, add 2.0 mL of anhydrous toluene and stir at 50°C for 15 hours; after TLC confirms that the reaction is complete, use 15.0 mL of ethyl acetate as eluent, and pass through a 2 cm silica gel short column to remove inorganic salts; then the organic phase is removed by rotary evaporation. After the solvent, a mixture of petroleum ether and ethyl acetate with a volume ratio of 5:1 was used as an eluent for column chromatography separation, and finally α-(4)-methoxycarbonylphenylvinylbenzene was obtained by distillation with a rotary evaporator The base sulfone was 77.9 mg, and the yield was 86%. The analysis data is as follows:
[0029] 1 HNMR (500MHz, CDCl 3 ): δ3.91(s,3H)...
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