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In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below.
[(2Z)-3-(benzenesulfonyl)-2-phenylprop-2-en-1-yl]oxy}(tert-butyl)dimethylsilane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
26%; 64%
In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below.
[(2Z)-3-(benzenesulfonyl)-2-phenylprop-2-en-1-yl]oxy}(tert-butyl)dimethylsilane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
15%; 80%
In an N2 charged glove box with oxygen and water levels ?0.1 ppm, to an oven-dried screwed vial were added complex 8 (51 mg, 0.05 mmol), K2CO3 (13.8 mg, 0.1 mmol, 2 eq.), boronic acids 3a (9 mg, 0.05mmol, 1 eq.) and THF (3 mL), then phenyl iodide 2a (10 mg, 0.05 mmol, 1 eq.) were also charged into the reaction mixture. The joint position between the vial and cap was sealed with black electric tape to save the nitrogen in the vial and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13 hours on the IKA electric stirring machine. After 15 hours, imidazole (17 mg, 0.25 mmol, 5 eq.) and TBSCl (22 mg, 0.15 mmol, 3 eq.) were added into the vial under air and stirred for another 2 hours at room temperature, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the formation of TBS protected allyl alcohol 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a (7 mg, 80%). The spectrum was same as above. The biphenyl product 4aa is also formed with about 1.6 mg (15% yield). There is no reaction occur without the presence of phenyl iodide, which was confirmed by the analysis of 31P NMR of crude reaction mixture.
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