* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: Under nitrogen atmosphere, a sealable reaction tube equipped with a magnetic stirrer bar was charged with azole (0.50 mmol), sodium arylsulfinate (1.0 mmol), Pd(OAc)2 (0.025 mmol), Cu(OAc)2 (1.0 mmol), CF3COOH (0.50 mmol), and dimethylglycol (2.0 mL). The rubber septum was then replaced by a Teflon-coated screw cap, and the reaction vessel placed in an oil bath at 120 C for 24 h. After the reaction was completed, it was cooled to room temperature and the mixture was treated with K2CO3 solution (1.0 mol/L, 3.0 mL), then extracted with ethyl acetate. The resulting solution was dried by Na2SO4 then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluant: petroleum ether/ethyl acetate=12:1, v/v) to give the desired product.
3-(4-methylphenylsulfanyl)propionic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%Chromat.
With silver(I) acetate; palladium dichloride; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation;
General procedure: Aryl sulfinate metal salt (0.36 mmol or 0.18 mmol), PdCl2 (0.06 mmol), AgNO3(0.6 mmol), DMF/DMSO (v/v = 19/1, 2 mL), and thiol (0.3 mmol) were added to the microwave tube. The tube was sealed and stirred for 5 min at ambient temperature. The tube was then heated at 40W for 10 min at 120 °C. After cooling down, the resulting suspensions were filtered off and washed with CH2Cl2. A small amount of silica gel was added into the filtrate, and then evaporated. The residue was purified by flash chromatography on silica with hexane/EA to provide the desired product.
3-(4-methylphenylsulfanyl)propionic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
37%Chromat.
With silver nitrate; palladium dichloride; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation;
General procedure: Aryl sulfinate metal salt (0.36 mmol or 0.18 mmol), PdCl2 (0.06 mmol), AgNO3(0.6 mmol), DMF/DMSO (v/v = 19/1, 2 mL), and thiol (0.3 mmol) were added to the microwave tube. The tube was sealed and stirred for 5 min at ambient temperature. The tube was then heated at 40W for 10 min at 120 °C. After cooling down, the resulting suspensions were filtered off and washed with CH2Cl2. A small amount of silica gel was added into the filtrate, and then evaporated. The residue was purified by flash chromatography on silica with hexane/EA to provide the desired product.
3-(4-methylphenylsulfanyl)propionic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%Chromat.
With silver carbonate; palladium dichloride; In tetrahydrofuran; at 120℃; for 0.166667h;Microwave irradiation;
General procedure: Aryl sulfinate metal salt (0.36 mmol or 0.18 mmol), PdCl2 (0.06 mmol), AgNO3(0.6 mmol), DMF/DMSO (v/v = 19/1, 2 mL), and thiol (0.3 mmol) were added to the microwave tube. The tube was sealed and stirred for 5 min at ambient temperature. The tube was then heated at 40W for 10 min at 120 °C. After cooling down, the resulting suspensions were filtered off and washed with CH2Cl2. A small amount of silica gel was added into the filtrate, and then evaporated. The residue was purified by flash chromatography on silica with hexane/EA to provide the desired product.
3-(4-methylphenylsulfanyl)propionic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%Chromat.
With silver nitrate; palladium dichloride; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 120℃; for 0.166667h;Microwave irradiation;
General procedure: Aryl sulfinate metal salt (0.36 mmol or 0.18 mmol), PdCl2 (0.06 mmol), AgNO3(0.6 mmol), DMF/DMSO (v/v = 19/1, 2 mL), and thiol (0.3 mmol) were added to the microwave tube. The tube was sealed and stirred for 5 min at ambient temperature. The tube was then heated at 40W for 10 min at 120 °C. After cooling down, the resulting suspensions were filtered off and washed with CH2Cl2. A small amount of silica gel was added into the filtrate, and then evaporated. The residue was purified by flash chromatography on silica with hexane/EA to provide the desired product.
ethyl 4-bromo-1-tosyl-1H-pyrazole-3-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
94%
With N-Bromosuccinimide; In ethyl acetate; at 25℃; for 12h;
In the drying tube was added 70mg of 3-pyrazolylEthyl acetateAnd 178mg of methyl benzene sulfinateSodium, added 267mg of NBS. 2mL ethyl acetate was then added to dissolve the solid, the reaction solution was stirred at 25 12 hours. After completion of the reaction, ethyl acetate and water extraction, the resulting organic phase was concentrated on a rotary evaporator, silica gel column (ethyl acetate and petroleum ether, the volume ratio of 1: 3) to give 175 mg of product, 94percent yield , the following reaction formula:
72%
With N-Bromosuccinimide; In ethyl acetate; at 25℃; for 12h;
General procedure: Pyrazoles 4 (0.5 mmol), sodium sulfinate 2 (1.0 mmol) and NBS or NIS (1.5 mmol) were dissolved in 2 mL of EtOAc solvent. the reaction mixture was stirred at room temperature under air for 12 h. After the reaction, the resulting mixture was extracted with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and the solvent was then removed under vacuum. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate, 3:1) to afford the corresponding product.
With [bis(acetoxy)iodo]benzene; at 20℃; for 0.25h;
General procedure: Iodobenzene diacetate (DIB, 0.24 mmol, 1.2 equiv) was added at room temperature to avigorously stirred solution of dichloromethane (0.5 mL), alcohol (0.5 mL), sulfinate (0.2mmol, 1 equiv) and acetic acid (0.01 to 0.05 mL) or TBAC (55.5 mg, 0.2 mmol, 2 equiv) tosolve the sulfonate salt. The mixture was then stirred for 15 min (followed by TLC with amixture of acetic acid/ethyl acetate/hexane) and then filtered on silica with ethyl acetate.The residue was purified by silica gel chromatography with a mixture of ethylacetate/hexane to give sulfonate product 4, 6 and 8.
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