Method for synthesizing alpha-arylvinyl phosphonate in the presence of catalyst Pd
A technology of aryl vinyl phosphonate and bromovinyl phosphonate is applied in the field of Pd-catalyzed α-aryl vinyl phosphonate synthesis, which can solve the problem of lack of enlarged application prospects, severe reaction conditions, low reaction efficiency, etc. problem, to achieve the effect of high reaction efficiency, low catalyst dosage, and strong functional group compatibility
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Embodiment 1
[0029] Add 0.4 mmol of diethyl α-bromovinylphosphonate, 0.6 mmol of phenylboronic acid, 0.02 mmol of palladium acetate, 2.0 mmol of potassium carbonate, and 0.04 mmol of tri-tert-butylphosphine tetrafluoroborate into a Schlenk reaction tube (10 mL). mmol, put N in vacuum 2 Cycle three times. in N 2 Under air protection, add 2.0 mL of anhydrous toluene, and stir at room temperature for 15 h; after TLC confirms that the reaction is complete, the reaction mixture uses ethyl acetate as eluent, and passes through a 2 cm silica gel short column to remove inorganic salts to obtain an eluent. The eluate is distilled by a rotary evaporator to remove ethyl acetate and toluene, and then the mixture of petroleum ether and ethyl acetate with a volume ratio of 3:1 is used as an eluent to separate by column chromatography and distilled by a rotary evaporator to obtain α- Diethyl phenylvinylphosphonate 95.0 mg, yield 99%. The analysis data is as follows:
[0030] 1 H NMR (500 MHz, CDCl ...
Embodiment 2
[0032] To a Schlenk reaction tube (50 mL), add 5.0 mmol of diethyl α-bromovinylphosphonate, 7.5 mmol of phenylboronic acid, Pd(OAc) 2 0.05mmol, K 2 CO 3 10.0 mmol, t -Bu 3 P?HBF 4 0.25 mmol, evacuated into N 2 Oxygen removal, at N 2 Under air protection, add 10.0 mL of anhydrous toluene, and stir at room temperature for 15 h; The liquid is distilled to remove ethyl acetate and toluene, and then the mixed solution of petroleum ether and ethyl acetate with a volume ratio of 3:1 is used as an eluting agent, separated by column chromatography, and distilled to obtain α-phenylvinylphosphonic acid diethyl The ester was 1.18 g, and the yield was 98%.
Embodiment 3
[0034] To a Schlenk reaction tube (10 mL), add 0.5 mmol of diethyl α-bromovinylphosphonate, 0.8 mmol of phenylboronic acid, Pd(OAc) 2 0.02 mmol, K 2 CO 3 1 mmol, t -Bu 3 P?HBF 4 0.02 mmol, evacuated into N 2 Oxygen removal, at N 2 Under air protection, add 4.0 mL of anhydrous toluene, and stir at room temperature for 15 h; The liquid is distilled to remove ethyl acetate and toluene, and then the mixed solution of petroleum ether and ethyl acetate with a volume ratio of 3:1 is used as an eluting agent, separated by column chromatography, and distilled to obtain α-phenylvinylphosphonic acid diethyl Esters, the yield is 98.5%.
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