A kind of branched allyl compound, preparation method and application
A technology of compound and branched alkenes, which is applied in the field of branched allyl compounds, can solve the problems of low construction rate of multichiral center compounds, few branched allyl products, complex ligand skeletons, etc., and achieve high Good selectivity, environmental friendliness, and atom economy
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Embodiment 1
[0201] Under argon atmosphere, add propiophenone (0.4mmol) and 2.0mL toluene into a 10mL reaction tube, add 0.4mL lithium hexamethyldisilazide (1.0M in THF) at 0°C, return to room temperature and stir for 30min , in another 5mL reaction tube, add allylpalladium(II) chloride dimer (1.9mg, 0.005mmol), SIPr.HCl (its structural formula is The system name is 1,3-bis(2,6-diisopropylphenyl)imidazolium hydrochloride, cas 258278-25-0) (4.4mg, 0.006mmol) and toluene (1.0mL), at 0°C Add 25 μL of potassium tert-butoxide (1.0M in THF), stir at room temperature for 30 min, combine the two reaction tubes and add tert-butyl cinnamyl carbonate (0.2 mmol), stir the reaction at room temperature for 24 h, add 0.5 mL of water to quench , dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the product was obtained by column chromatography Total yield 99%, 1 The purity by H NMR is greater than 95%.
[0202] 1 H NMR (400MHz, CDCl 3 ):(taken as a mixture of...
Embodiment 2
[0204] Under argon atmosphere, add butyrophenone (0.4mmol) and 2.0mL toluene into a 10mL reaction tube, add 0.4mL lithium hexamethyldisilazide (1.0M in THF) at 0°C, return to room temperature and stir 30min, in another 5mL reaction tube, add allylpalladium(II) chloride dimer (1.9mg, 0.005mmol), SIPr.HCl (4.4mg, 0.006mmol) and toluene (1.0mL), 0 ℃ Add 25 μL of potassium tert-butoxide (1.0M in THF) at room temperature and stir for 30 min at room temperature. Then, combine the two reaction tubes and add tert-butyl cinnamyl carbonate (0.2 mmol). After the reaction is stirred at room temperature for 24 h, add 0.5 mL of water to quench extinguished, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the product was obtained by column chromatography Total yield 99%, 1 The purity by H NMR is greater than 95%.
[0205] 1 H NMR (400MHz, CDCl 3 ):(taken as a mixture of diastereomers): δ(major diastereomer)7.74(d,J=7.8Hz,2H),7.56-7.01(m,8H),...
Embodiment 3
[0207] Under argon atmosphere, the (0.4mmol) and 2.0mL toluene were added to a 10mL reaction tube, and 0.4mL lithium hexamethyldisilazide (1.0M in THF) was added at 0°C, and stirred at room temperature for 30min, and in another 5mL reaction tube Add allylpalladium(II) chloride dimer (1.9mg, 0.005mmol), SIPr.HCl (4.4mg, 0.006mmol) and toluene (1.0mL), add 25μL potassium tert-butoxide (1.0 M in THF), after stirring at room temperature for 30 min, the two reaction tubes were combined and added tert-butyl cinnamyl carbonate (0.2 mmol), and the reaction was stirred at room temperature for 24 h, quenched by adding 0.5 mL of water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the product was obtained by column chromatography Total yield 99%, 1 The purity by H NMR is greater than 95%.
[0208] 1 H NMR (400MHz, CDCl 3 ): δ(major diastereomer) 7.88(d, J=7.2Hz, 2H), 7.51(t, J=7.2Hz, 1H), 7.41(t, J=7.6Hz, 2H), 7.30-7.22(m, 5H ),7.20-...
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