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CAS No. : | 34176-08-4 | MDL No. : | MFCD09065037 |
Formula : | C6H4BrNaO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FJSOUHVHPWODGS-UHFFFAOYSA-M |
M.W : | 243.05 | Pubchem ID : | 23670685 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper diacetate In acetonitrile at 60℃; for 3 h; | General procedure: A mixture of the sodium arylsulfinate (1 mmol), Cu(OAc)2 (0.5 mmol)and CH3CN (1 mL) was stirred at 60 °C in air for 3 h. After this, themixture was cooled to room temperature and filtered through a filterpaper. The organic phases were evaporated under reduced pressure andthe residue was subjected to flash column chromatography (silica gel,ethyl acetate/petroleum ether = 1/10) to obtain the desired product.All products are known compounds and were characterised by 1HNMR, 13C NMR and HRMS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With acetic acid In water at 100℃; for 1.5h; | 7.1 To a suspension of sodium 4-bromophenylsulfinate (130 g, 0.53 mol) in water (600 mL) was added acrylonitrile (70 mL, 1.07 mol) and acetic acid (62 mL, 1.07 mol). The reaction was stirred for 1.5 hours at 1000C then cooled to room temperature. The solid was filtered off, washed thoroughly with water and dried over P2O5 to give 3-[(4-bromophenyl)sulfonyl]propanenitrile (125 g. 85%). δH (400 MHz, CDCl3): 7.27-7.22 (4 H, m), 2.85 (2 H, t, J = 7.6 Hz), 2.30 (2 H, t, J = 7.6 Hz). |
With sodium dihydrogenphosphate; hydroquinone In water | ||
With acetic acid In water at 100℃; for 1.5h; | 1.1 To a suspension of sodium 4-bromophenylsulfinate dihydrate (130 g, 0.53 mol) in water (600 mL) was added acrylonitrile (70 mL, 1.07 mol) and acetic acid (62 mL, 1.07 mol). The reaction was stirred for 1.5 h at 100 °C then cooled to room temperature. The solid was filtered off, washed thoroughly with water and dried over P205 to give 3-[(4-bromophenyl)sulfonyl]propanenitrile (125 g). δH (400 MHz, CDCI3): 7.27-7.22 (4H, m), 2.85 (2H, t, J 7.6), 2.30 (2H, t, J 7.6). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 8h; | |
68% | With sodium dihydrosulfite; anhydrous sodium carbonate In lithium hydroxide monohydrate at 40℃; for 2h; | |
With potassium dihydrogen orthophosphate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 30 - 60℃; for 18h; |
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 100℃; for 0.42h; Microwave irradiation; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 8h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 70 - 80℃; for 4h; | General procedure for the preparation of sodium sulfinates General procedure: 4-Methoxybenzenesulfinic acid sodium salt (1j) was prepared by heating 2.5 g of sodium sulfite, 2.06 g of 4-methoxybenzenesulphonyl chloride, and 1.68 g of sodium bicarbonate in 9.6 mL of water at 70-80 °C for 4 h. After cooling to room temperature, water was removed under vacuum and the residue was extracted by ethanol, recrystallization as a white solid, the yield was 67% (1.34 g). Similarly, other sodium arenesulfinates were prepared from their corresponding sulphonyl chlorides. | |
With lithium hydroxide monohydrate; Sodium hydrogenocarbonate; anhydrous sodium sulphite at 80℃; for 4h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 8h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 4h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 4h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 8h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 4h; | General procedure for the synthesis of compound 3 General procedure: Sulfonyl chloride 1 (0.2 mmol) was added into a solution of Na2SO3 (2.0 equiv) and NaHCO3 (2.0 equiv) in H2O (1.0 mL). The mixture was stirred at 80°C for 4h. After evaporation of water, PhNHSCF3 2 (0.3 mmol), 4-methylbenzenesulfonic acid (0.5mmol) and DCE (2 ml) were added. The mixture was stirred at room temperature. After completion of the reaction as indicated by TLC, the reaction mixture was filtered by sand core funnel with silica gel and washed by CH2Cl2. The volatiles were removed and the residue was purified by flash column chromatography (SiO2) to provide the final products 3. | |
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 4h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 8h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 70 - 80℃; for 4h; Inert atmosphere; | 3.2. General Procedure for the Preparation of Sodium Sulfinates General procedure: 4-Methoxybenzenesulfinic acid sodium salt (2e) was prepared by heating 2.5 g of sodium sulfite,2.06 g of 4-methoxybenzenesulphonyl chloride, and 1.68 g of sodium bicarbonate in 9.6 mL of waterat 70-80 C for 4 h. After cooling to room temperature, water was removed under vacuum and theresidue was extracted by ethanol, recrystallization as a white solid, the yield was 67% (1.34 g). Similarly,other sodium arenesulfinates were prepared from their corresponding sulfonyl chlorides. | |
With sodium hydrogen sulphite; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 4h; | ||
With anhydrous sodium sulphite | ||
With sodium dihydrosulfite | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 12h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 3h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 70 - 80℃; for 4h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 10h; | ||
With Sodium hydrogenocarbonate; anhydrous sodium sulphite In lithium hydroxide monohydrate at 80℃; for 3h; | 2) Typical procedure of the preparation for sodium arylsulfinates General procedure: The ethyl 4-(chlorosulfonyl)benzoate (20 mmol, 1.0 equiv, 4.98 g) was dissolved in water (50 mL). Sodium sulfite (40 mmol, 2.0 equiv, 5.04 g) and sodium bicarbonate(40 mmol, 2.0 equiv, 3.4 g) were added, and the reaction mixture was stirred at 80 oCfor 3 h. The solvent was evaporated and ethanol (100 mL) was added to the residue.The suspension was heated to 80 oC for 10 min, refluxed and filtered. The filtrate wasevaporated, and then ethanol (100 mL) was added and heated to 80 oC for 10 min,refluxed and filtered at the second time. The solvent was evaporated under vacuum togive sodium 4-(ethoxycarbonyl)benzenesulfinate (1c, 2.7 g, 58%) as white powders. | |
With Sodium hydrogenocarbonate; Na2S2O3 In lithium hydroxide monohydrate at 80℃; for 4h; | ||
With Sodium hydrogenocarbonate In lithium hydroxide monohydrate at 80℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With 1,4-diaza-bicyclo[2.2.2]octane; palladium(II) hydroxide; trifluoroacetic acid In 1,4-dioxane; water at 120℃; for 20h; Inert atmosphere; | 4-(4-bromophenyl)-4-phenylbutan-2-one (3q) (CAS: 1005497-31-3)[6] The reaction was conducted with Pd(OH)2 (1.4 mg, 0.01 mmol), DABCO (2.3 mg, 0.02 mmol),sodium 4-bromobenzenesulfinate (1g, 96.8 mg, 0.4 mmol), (E)-4-phenylbut-3-en-2-one (2a, 29.2mg, 0.2 mmol) and charged with argon (1 atm). TFA (0.1 mL, 6.7 equiv) and 1,4-dioxane (0.2 mL),H2O (0.2 mL) were added to the sealed reaction vessel by syringe. The resulting solution wasstirred at 120 °C for 20 h. After cooling to room temperature, the volatiles were removed undervacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethylacetate = 30:1) to give 3q as pale yellow oil; yield 70%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With scandium tris(trifluoromethanesulfonate) In water at 30℃; for 2h; Ionic liquid; | General procedure for the synthesis of thiosulfonates General procedure: To a solution of 1 (0.3 mmol) and 2 (0.36 mmol) in [BMIM]PF6 (3 mL) and H2O (1 mL), Sc(OTf)3 was added at 30 °C. The mixture solution was stirred at 30 °C for respective time. After the completion of the reaction, as monitored by TLC and GC-MS analysis, the mixture was washed with water and extracted with diethyl ether. The organic phase was concentrated and the resulting residue was purified by column chromatography on silica gel (300-400 mesh) with petroleum ether-EtOAc as eluent to provide the desired thiosulfonates 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With di-tert-butyl peroxide; palladium diacetate In acetonitrile at 60℃; for 12h; | Synthesis of the products; general procedure General procedure: A mixture of the sodium arylsulfinate (1 mmol), Pd(OAc)2 (1 mol%) and DTBP (0.5 mmol) was stirred at 60 °C for 12 h in CH3CN (1 mL). Afterwards, the reaction solution was filtered through a filter paper and the organic phase was evaporated under reduced pressure at 40 °C. The residue was purified on a SiO2 column (ethyl acetate/hexane = 1:20) to afford the desired product. |
77% | With copper(I) oxide; oxygen; palladium dichloride In water at 100℃; for 30h; Sealed tube; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In N,N-dimethyl-formamide at 90℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper dichloride; palladium dichloride In 1,4-dioxane at 90℃; for 8h; regioselective reaction; | α-Benzyl-β-keto Esters 3 from Baylis-Hillman Adducts; General Procedure General procedure: A mixture of sulfinic acid sodium salt 2 (0.60 mmol), PdCl2 (0.10 equiv), Baylis-Hillman adduct 1 (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10-mL round- bottomed flask. The mixture was vigorously stirred at 90°C for 8 h. After cooling to r.t., the mixture was partitioned between EtOAc (25.0 mL) and H2O (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel, and the organic layer was washed with H2O and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient, hexane-EtOAc) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With copper dichloride; palladium dichloride In 1,4-dioxane at 90℃; for 8h; regioselective reaction; | α-Benzyl-β-keto Esters 3 from Baylis-Hillman Adducts; General Procedure General procedure: A mixture of sulfinic acid sodium salt 2 (0.60 mmol), PdCl2 (0.10 equiv), Baylis-Hillman adduct 1 (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10-mL round- bottomed flask. The mixture was vigorously stirred at 90°C for 8 h. After cooling to r.t., the mixture was partitioned between EtOAc (25.0 mL) and H2O (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel, and the organic layer was washed with H2O and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient, hexane-EtOAc) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With copper dichloride; palladium dichloride In 1,4-dioxane at 90℃; for 8h; regioselective reaction; | α-Benzyl-β-keto Esters 3 from Baylis-Hillman Adducts; General Procedure General procedure: A mixture of sulfinic acid sodium salt 2 (0.60 mmol), PdCl2 (0.10 equiv), Baylis-Hillman adduct 1 (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10-mL round- bottomed flask. The mixture was vigorously stirred at 90°C for 8 h. After cooling to r.t., the mixture was partitioned between EtOAc (25.0 mL) and H2O (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel, and the organic layer was washed with H2O and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient, hexane-EtOAc) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With copper dichloride; palladium dichloride In 1,4-dioxane at 90℃; for 8h; regioselective reaction; | α-Benzyl-β-keto Esters 3 from Baylis-Hillman Adducts; General Procedure General procedure: A mixture of sulfinic acid sodium salt 2 (0.60 mmol), PdCl2 (0.10 equiv), Baylis-Hillman adduct 1 (0.50 mmol), and CuCl2 (1.0 equiv) was dissolved in 1,4-dioxane (3.0 mL) in a 10-mL round- bottomed flask. The mixture was vigorously stirred at 90°C for 8 h. After cooling to r.t., the mixture was partitioned between EtOAc (25.0 mL) and H2O (25.0 mL) and filtered through a celite pad. The filtrate was transferred to a separatory funnel, and the organic layer was washed with H2O and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient, hexane-EtOAc) to afford the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrinatoiron(III) chloride; D-glucose; water monomer; oxygen; glucose oxidase at 20℃; for 2h; | General procedure for the synthesis of β-ketosulfones General procedure: To a mixture of alkenes/alkynes (0.5 mmol), sodium benzenesulfinate(0.5 mmol), glucose (1.1 mmol) in water (2 ml), hemoproteins(heme concentration: 0.06 mol%), GOX (42 U/ml), was added. The reaction mixture was then stirred at room temperature in a round bottom flask for 2 h, with oxygen added at a rate of 1 mL/min. The reaction was monitored by TLC. When the reaction was complete, the crude mixture was extracted with ethyl acetate. Then the organic phase was dried over sodium sulfate and concentrated under reduced pressure. Finally, the desired product was obtained by flash column chromatography with petroleum ether/ethyl acetate (4/1) as an eluent. All the isolated products were well characterized by their 1H spectral analysis. |
81% | With potassium peroxodisulfate; water monomer at 20℃; for 18h; | |
81% | With tetra-n-butylammonium hexafluoridophosphate In acetonitrile at 20℃; for 8h; Electrochemical reaction; |
13% | With hydrogenchloride In water monomer; N,N-dimethyl-formamide at 30℃; for 14h; Sealed tube; | 17 Example 17 Weigh styrene (20.8 mg, 0.2 mmol), p-bromobenzenesulfinic acid sodium salt (97.3 mg, 0.4 mmol), and 36% concentrated hydrochloric acid (33.9 μL, 0.4 mmol).Using N,N-dimethylformamide (2.0 mL) as a solvent, the reaction tube (25 mL) was sealed in a 30° C. oil bath and stirred magnetically. React for 14 hours. Subsequently, the reaction mixture was cooled to room temperature and then transferred to a separatory funnel. The reaction mixture was adjusted to pH = 11 with saturated sodium carbonate solution and 20 mL of water was added. The mixture was extracted with ethyl acetate (4×10 mL), and the organic phases were combined and used again. Saturated brine (4×15 mL) was washed with water, and the combined organic phase was dried over anhydrous Na2SO4. Filter, concentrate the solvent under reduced pressure, and finally obtain pure product 2-((4-bromophenyl)sulfonyl)-1-phenylethyl-1 by thin layer chromatography (petroleum ether/ethyl acetate=3:1) -ketone. Yellow solid, the yield is 13%. |
13% | With hydrogenchloride In water monomer; N,N-dimethyl-formamide at 30℃; for 14h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With dihydrogen peroxide; iodine; phosphonic acid diethyl ester for 0.166667h; Sealed tube; Heating; Microwave irradiation; Green chemistry; | |
91% | With Diethyl phosphonate; iodine; dimethyl sulfoxide at 100℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction; | |
71% | With bis(trichloromethyl) carbonate In acetonitrile for 2h; Cooling with ice; |
70% | With ammonium iodide In N,N-dimethyl-formamide at 135℃; for 20h; Sealed tube; regioselective reaction; | |
66% | With bis(trichloromethyl) carbonate In acetonitrile Schlenk technique; Inert atmosphere; | Electrophilic Thiolation of Indoles or N-Methylpyrrole; General Procedure General procedure: A 10 mL Schlenk tube equipped with a magnetic stirring barwas charged with RSO2Na (0.4 mmol) and the appropriateindole or N-methylpyrrole (0.2 mmol). The tube was then evacuatedand backfilled with dry N2 (this operation was repeatedthree times), and the mixture was stirred at -78 °C for theinitial time. A solution of triphosgene (0.4 mmol) in MeCN (1mL) was added slowly from a syringe, and the mixture wasstirred at -78 °C for 1 h. When the reaction was complete, themixture was warmed to rt and diluted with CH2Cl2 (20 mL). Themixture was then washed with 5% aq NaHCO3 (10 mL), and thecombined organic phase was dried (Na2SO4) and concentratedunder reduced pressure. The residue was purified by columnchromatography (silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With iron(III) chloride; dipotassium peroxodisulfate; oxygen In water at 20℃; for 7h; Green chemistry; | General procedure for the one-pot synthesis of β-keto sulfones 3a-w General procedure: A mixture of alkyne 1 (0.25 mmol), sodium sulfinate 2 (0.375 mmol), FeCl3 (20 mol %),K2S2O8 (20 mol %), and water (3 mL) was stirred at rt in an open flask for 6-9 h(Table 2). After completion of the reaction (monitored by TLC), the mixture was extracted with EtOAc (3 5 mL). The combined organic phases were dried over anhyd. Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a mixture of EtOAc-n-hexane (1:4) as eluent to afford an analytically pure sample of β-keto sulfones 3 (Table 2). |
78% | Stage #1: sodium 4-bromobenzenesulfinate With 2-Picolinic acid; copper(l) iodide; trimethylsilylazide In methanol for 0.0833333h; Green chemistry; Stage #2: phenylacetylene With oxygen In methanol at 25 - 28℃; Irradiation; Green chemistry; | |
59% | With heme b; D-glucose; water; oxygen; glucose oxidase at 20℃; for 2h; | General procedure for the synthesis of β-ketosulfones General procedure: To a mixture of alkenes/alkynes (0.5 mmol), sodium benzenesulfinate(0.5 mmol), glucose (1.1 mmol) in water (2 ml), hemoproteins(heme concentration: 0.06 mol%), GOX (42 U/ml), was added. The reaction mixture was then stirred at room temperature in a round bottom flask for 2 h, with oxygen added at a rate of 1 mL/min. The reaction was monitored by TLC. When the reaction was complete, the crude mixture was extracted with ethyl acetate. Then the organic phase was dried over sodium sulfate and concentrated under reduced pressure. Finally, the desired product was obtained by flash column chromatography with petroleum ether/ethyl acetate (4/1) as an eluent. All the isolated products were well characterized by their 1H spectral analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper(l) iodide; sodium acetate In 1,2-dichloro-ethane at 25℃; for 3h; | Synthesis; typical procedure General procedure: A mixture of potassium arylfluoborate (1 mmol), sodium aryl sulfinate (1 mmol), CuI (0.1 mmol), sodium acetate (1.2 mmol) and DCE (2 mL) was stirred at 25 °C under air for 3 h. After filtration, the organic phases were evaporated under reduced pressure, and the residue was subjected to flash column chromatography [silica gel, ethyl acetate/petroleum ether (60-90 °C) = 1/8] to obtain the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With p-nitrobenzenesulfonic acid; palladium diacetate; In tetrahydrofuran; water; at 80℃; for 48h;Inert atmosphere; Schlenk technique; | General procedure: Under a N2 atmosphere, a Schlenk tube was charged with 2-aminobenzonitrile 1 (0.3 mmol),sodium arylsulfinate 2 (0.6 mmol), Pd(OAc)2 (10 mol percent), bpy (20 mol percent), p-NBSA (10 equiv), THF (2 mL), and H2O (1 mL) at room temperature. The reaction mixture was stirred vigorously at 80 °C for 48 h. The mixture was poured into ethyl acetate, which was washed with saturated NaHCO3 (2 × 10 mL) and then brine (1 × 10 mL). After the aqueous layer was extracted with ethyl acetate, the combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane/ethyl acetate) to afford the desired products 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper diacetate; In acetonitrile; at 60℃; for 3h; | General procedure: A mixture of the sodium arylsulfinate (1 mmol), Cu(OAc)2 (0.5 mmol)and CH3CN (1 mL) was stirred at 60 C in air for 3 h. After this, themixture was cooled to room temperature and filtered through a filterpaper. The organic phases were evaporated under reduced pressure andthe residue was subjected to flash column chromatography (silica gel,ethyl acetate/petroleum ether = 1/10) to obtain the desired product.All products are known compounds and were characterised by 1HNMR, 13C NMR and HRMS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: sodium 4-bromobenzenesulfinate; propargyl bromide With tetrabutyl ammonium fluoride In tetrahydrofuran; water; toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With palladium 10% on activated carbon In tetrahydrofuran; water; toluene at 20℃; for 8h; Reflux; Inert atmosphere; | A representative synthetic procedure of skeleton 1 is as follows General procedure: n-Bu4NF (1.0 M in THF, 0.2 mL, 0.2 mmol) was added to a solution of propargyl bromide (2a) (80% in toluene, 150 mg, 1.0 mmol)or 1-bromopent-2-yne (2b) (150 mg, 1.0 mmol) in 1,4-dioxane (5 mL) at rt. Then, RSO2Na (3a-k) (3.0 mmol) in hot water (1 mL) was slowly added to the reaction mixture. The reaction mixture was stirred at rt for 10 min. Next, Pd/C (10% in carbon, 11 mg, 0.1 mmol) was added to the stirred solution at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled, filtered, washed, and concentrated under reduced pressure. The residue was diluted with water (10 mL) and the mixture was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc = 6/1~2/1) afforded skeleton 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper diacetate; palladium diacetate In 1,4-dioxane; diethylene glycol dimethyl ether at 120℃; for 24h; regioselective reaction; | General Procedure for the Synthesis of 3 and 4 General procedure: A reaction vessel was charged with thiazolo[3,2-b]-1,2,4-triazoles 1 (0.5 mmol), sodium arylsulfinates 2 (1 mmol),Pd(OAc)2 (5 mol%), Cu(OAc)2 (2 equiv), and dioxane-diglyme (1:2; 1 mL). The mixture was stirred at 120 °C andmonitored by TLC. After the completion of the reaction, themixture was poured into H2O (10 mL), and extracted withEtOAc (3 × 10 mL). The combined extract was dried withanhyd MgSO4. The solvent was removed and the crudeproduct was separated by column chromatography (elutedwith petroleum ether-EtOAc) to give the desired products 3and 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With copper diacetate; palladium diacetate In 1,4-dioxane; diethylene glycol dimethyl ether at 120℃; for 24h; regioselective reaction; | General Procedure for the Synthesis of 3 and 4 General procedure: A reaction vessel was charged with thiazolo[3,2-b]-1,2,4-triazoles 1 (0.5 mmol), sodium arylsulfinates 2 (1 mmol),Pd(OAc)2 (5 mol%), Cu(OAc)2 (2 equiv), and dioxane-diglyme (1:2; 1 mL). The mixture was stirred at 120 °C andmonitored by TLC. After the completion of the reaction, themixture was poured into H2O (10 mL), and extracted withEtOAc (3 × 10 mL). The combined extract was dried withanhyd MgSO4. The solvent was removed and the crudeproduct was separated by column chromatography (elutedwith petroleum ether-EtOAc) to give the desired products 3and 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With tert.-butylhydroperoxide; iodine In water; toluene at 90℃; for 12h; | 4.2. General procedure for preparation of iodine-mediateddecarboxylation between cinnamic acid and sodium benzenesulfinate General procedure: A 25 mL tube was charged with cinnamic acid (0.3 mmol), sodiumbenzene sulfinate (1.2 mmol), iodine (2 equiv), TBHP in H2O(0.6 mmol) and toluene (2 mL). The resulting reaction mixture waskept stirring at 90 C for 12 h. Upon completion of the reaction, thereaction mixturewas cooled to room temperature. After removal ofthe solvent, the residue was subjected to column chromatographyon silica gel using ethyl acetate and petroleum ether mixtures toafford the desired product in high purity. |
81% | With potassium carbonate In dimethyl sulfoxide at 100℃; for 10h; Green chemistry; | |
81% | With iodine; potassium carbonate In water at 60℃; for 10h; Green chemistry; |
70% | With tert.-butylhydroperoxide In water; dimethyl sulfoxide at 20℃; for 12h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With manganese (II) acetate tetrahydrate In dimethyl sulfoxide at 110℃; for 12h; | 1. General Procedure: General procedure: To a 25 ml round bottom flask were added cinnamic acid (0.5 mmol) , aromatic sulfinic acidsodium salt (1.5 mmol), Mn(OAc)2•4H2O(6.13 mg, 0.025 mmol) and DMSO (2ml). The round bottom flask was stirred under air at 110 °C for 12 h. The reaction mixture was cooled to roomtemperature and washed three times with saturated sodium chloride, extracted with EtOAc, andconcentrated in vacuo. The resulting residue was purified by flash column chromatography usinghexanes:EtOAc (8:1) as the eluent. All compounds are characterized by 1H NMR, 13C NMR,LRMS and their comparison to literature values |
56% | With palladium diacetate; silver carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 75℃; for 6h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With {(Pd{Fe(η5-C5H5)(η5-C5H3C(CH3)=NC6H4CH3-4)}(μ-Cl))2}; potassium carbonate In dimethyl sulfoxide at 110℃; for 12h; Inert atmosphere; | 4.3. General procedure for the first palladium-catalyzed denitrated coupling of nitroarenes with aryl sulfinates General procedure: Under N2 atmosphere, a reaction vessel was charged with a mixture of sodium sulfinates 1 (0.6 mmol), nitroarenes 2 (0.3 mmol), palladacycle I (0.75 mol%) and K2CO3 (1.0 equiv) in DMSO (2 ml) at room temperature. After that, the mixture was heated to 110 °C and incubated in an oil bath for 12 h under N2 atmosphere. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with brine three times. The combined organic solution was dried with Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by thin-layer chromatography on silica gel GF 254 (ethyl acetate/petroleum ether) to give the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | Stage #1: sodium 4-bromobenzenesulfinate With iodine at 20℃; for 0.333333h; Green chemistry; Stage #2: morpholine In ethanol at 20℃; for 3h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium hydrogen sulfite; iron(II) chloride In dimethyl sulfoxide at 60℃; for 12h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With tert.-butylhydroperoxide; 1,10-Phenanthroline; copper(II) perchlorate hexahydrate In decane; acetonitrile at 110℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With ammonium iodide In dimethyl sulfoxide at 20℃; for 7h; Electrolysis; | 4.23 A typical procedure for the electrosynthesis of β-keto sulfones General procedure: In a typical experiment, 1,3-dicarbonyl compounds (1 mmol), sodium sulfinates (1.2 mmol), DMSO (8 mL) and NH4I (4 mmol) were added to the undivided cell. The electrosynthesis was carried out in the undivided cell fitted with a Ni sheet cathode (2 cmx2.5 cmx0.02 cm) and a graphite rod anode at a constantcurrent (50 mA) at room temperature under magnetic stirring for 2 h and then continuously stirring for 5 h. After the reaction was finished, the electrolyte solution was decolorized with Na2S2O3, and then washed with distilled water (50 mL) and extracted withethyl acetate (10 mLx3). The solvent was removed under reduced pressure, and the crude product was purified by column chromatography on silica gel using petroleum ether-ethyl acetate (5:1) as eluent. |
16% | With iron(III) perchlorate hydrate In water; isopropyl alcohol at 78℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: 4-(benzoyloxy)morpholine; sodium 4-bromobenzenesulfinate In 1,2-dichloro-ethane at 30℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: With copper(ll) bromide In 1,2-dichloro-ethane for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium iodide In water; acetonitrile at 20℃; for 7h; Electrochemical reaction; | |
63% | With potassium iodide In water; acetonitrile at 20℃; for 7h; Electrolysis; | 4 Phenylacetylene was added toa three-necked flask (25mL)equipped with a stir bar and dried in an oven in advance.(0.3mmol), sodium p-bromobenzenesulfinate (0.9mmol), KI(1.0 equivalent), H2O (0.1mL) andCH3CN(10.0mL) are mixedThe mixture is obtained. The three-neck flask is equipped with platinum electrodes (1.0cmX1.0cm X0.2mm) as anode and cathode.Stir and electrolyze with a constant current of10mA at room temperaturefor 7h. After the reaction, transfer the reaction system to a 25mLeggplant-shaped flask and useHeidolphrotary evaporator (rotating speed 80-100rpm, temperature of 38C, vacuum degree of 0.1Mpa) rotary steaming treatment for 3min,The residue was then subjected to column chromatography using 200 mesh column chromatography silica gel (the developing solvent for column chromatography was petroleum ether and ethyl acetate, and petroleumThe volume ratio of ether: ethyl acetate is 20:1), the target compound (60.7mg, the yield is 63%) was isolated, and the alkynyl sulfone compound of the above structure was obtained by [[analytical purity of 98%]]. |
17% | With tert.-butylhydroperoxide; iodine In tetrahydrofuran; water at 30 - 32℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With iodine In water; acetonitrile at 70℃; for 12h; Green chemistry; regioselective reaction; | General procedure for the synthesis of β-keto sulfones 3 General procedure: A mixture of enol acetate 1 (1 mmol), sodium sulfinate 2 (1.2 mmol), I2 (1 mmol) and CH3CN + H2O (4:1,3 mL) was taken in a flask and stirred at 70 °C for 10-12 h (Table 2). After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with ethyl acetate (3 x 5 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated unde rreduced pressure. The resulting crude product was purified by column chromatography using a mixture of hexane/ethyl acetate (4:1) as eluent to afford an analytically pure sample of product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With p-toluenesulfonyl chloride In water at 20℃; for 0.666667h; Sealed tube; Green chemistry; regioselective reaction; | 2.1 General Procedure for the Synthesis of 3 General procedure: A solution of heterocyclic N-oxide (0.2 mmol), sodium sulfinate (0.2 mmol) and TsCl (49 mg, 0.26 mmol) in H2O (0.5 mL) was stirred under an air atmosphere at ambient temperature for a desired time (monitored by TLC). After the reaction was finished, the mixture was extracted with EtOAc (2 mL x 3) and the organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to obtain product 3. |
83% | With pyridine; tert.-butylhydroperoxide; iron(III) chloride hexahydrate In water; acetonitrile at 80℃; for 12h; Schlenk technique; | Typical synthetic procedure of 2-sulfonyl quinolines 3 General procedure: A Schlenk tube (35 ml) equipped with a magnetic bar was loaded with the solution of quinoline N-oxide 1 (0.5 mmol), sodium sulfinate 2 (1.0 mmol) and FeCl3*6H2O (20 mol%) in a mixture of CH3CN and H2O (5.0 ml, ca. 9:1 by volume). Then, TBHP (70% in decane, 1.0 mmol) and pyridine (1.0 mmol) were added to the solution dropwise via a syringe and the reaction mixture was stirred at 80 °C for 12 h. After the completion of the reaction (monitored by thin layer chromatography), the mixture was washed with brine (15 ml) and then was extracted with dichloromethane (15 ml * 3). The organic phase was combined and then concentrated. The oily crude product was purified by column chromatography using silica gel (-200-300 mesh) as stationary phase and a mixture of petroleum and ethyl acetate as eluent to give the desired product in the noted yields. |
76% | With dipotassium peroxodisulfate; copper(ll) bromide In nitromethane; water; 1,2-dichloro-ethane at 40℃; for 15h; Schlenk technique; Inert atmosphere; |
75% | With fluorosulfonyl fluoride; triethylamine In dimethyl sulfoxide at 40℃; for 16h; regioselective reaction; | 2. General procedure for synthesis of 3 General procedure: To a 25 mL double-necked flask was added 0.3 mmol of quinoline N-oxide, 0.9 mmol of sodium sulfonate, 1.5 mmol of Et3N, 2.5 mL of DMSO, and bubble SO2F2 into the mixture using a balloon combined with syringe needle. The mixture stirred for 16 h at 40 °C. The reaction mixture was diluted with 5 mL of water, and extracted with CH2Cl2 (3*20 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was further purified through flash column chromatography using the mixture of petroleum ether and ethyl acetate as eluent (PE : EA=10 : 1 - 4 : 1). |
70% | With tert.-butylhydroperoxide; iodine In water; N,N-dimethyl-formamide at 20℃; for 2h; | |
66% | With tetrabutylammonium tetrafluoroborate; acetic acid In water; acetonitrile at 20℃; for 2h; Inert atmosphere; | |
53% | With ferric nitrate In dimethyl sulfoxide at 120℃; for 0.333333h; Microwave irradiation; regioselective reaction; | Synthesis of 2-arylsulfonyl quinolines (3a-c); general procedure General procedure: Quinoline N-oxides 1 (0.3 mmol), sodium arylsulfinates 2 (0.45 mmol) and Fe(NO3)3 (0.09 mmol) in DMSO (3.0 mL) were added to a microwave reaction tube (5.0 mL). The reaction mixture was heated at 120 °C for 20 min under microwave irradiation. After reaction completion, the solvent was distilled under vacuum. Ethyl acetate (10 mL) was added to the residue, and washed with saturated sodium chloride solution (3 × 30 mL). The organic phase was dried over anhydrous NaSO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired products 3 using ethyl acetate/petroleum ether (1:10 to 1:5) as the eluent. All compounds were confirmedby IR, 1H NMR, 13C NMR and MS. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With copper(l) iodide; 1,10-Phenanthroline; potassium <i>tert</i>-butylate In dimethyl sulfoxide at 140℃; for 3h; Schlenk technique; Sealed tube; | 5 Example 5: Preparation of 4-bromobenzoic acid (4-Br-C6H4C00H) In a 20 mL dehydrated deoxygenated Schlenk tube, sodium p-bromobenzenesulfinate (0.2 mmol,(0 · 02 mmol, 3.81 mg), l, 10-o-phenanthroline (0.06 mmol, 10.8 mg), potassium tert-butoxide (0.6 mmol) , 67.3 mg), 2.5 mL of dimethyl sulfoxide (DMS0), and finally into the reaction tube into 0.1 MPa of C02.The sealed reaction tube was placed in a 140 ° C oil bath and heated and stirred for about 3 hours. Use 2 mL of 1 M hydrochloric acid to dissolve.The reaction solution was acidified and the system was extracted with ethyl acetate (4 mL x 5). The organic phase was collected and finally passed through a columnThe product was purified by chromatography and then dried to give a white solid powder 31.7 mg in 77% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: phenyl bromide With Aluminum Chloride; 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct In 1,2-dichloro-ethane at 25℃; for 4h; Stage #2: With Sodium hydrogenocarbonate In water monomer; 1,2-dichloro-ethane at 25℃; | |
91% | With Aluminum Chloride; 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct; Sodium hydrogenocarbonate In chloroform; water monomer at 20 - 30℃; | 4 Example 4: Preparation of sodium 4-bromobenzenesulfinate Under normal pressure, to a 100 mL three-necked flask with mechanical agitation,25 mL of trichloromethane, 2.1 mmol of bromobenzene,18.8 mmol of aluminum trichloride, 6.3 mmol of the above-mentioned self-made DABSO,And then heated to 30 , the reaction 12-14h, liquid chromatography to the reaction solution bromine content of less than 5%, and no longer lower, the reaction is over. The post-treatment operation was the same as in Example 1 to obtain 0.46 g of sodium 4-bromobenzenesulfinate as a white solid in 91% yield. |
75% | Stage #1: phenyl bromide With sulfur(IV) oxide at 50℃; for 2h; Inert atmosphere; Stage #2: With Sodium hydrogenocarbonate In water monomer Cooling with ice; | 2.2.2 2.2 Preparation of sodium p-bromobenzene sulfinate Accurately weigh bromobenzene (1mol, 112.5g) and acetamide-aluminum trichloride liquid coordination complex (0.5AA-AlCl ) (6 equiv.) into the three-necked flask with nitrogen protection and turn on stirring, wait until After the bromobenzene was completely dissolved, sulfur dioxide (1.5 equiv.) was introduced, and the reaction was carried out at 50° C. to the end of the reaction. The whole reaction was monitored by high performance liquid chromatography (HPLC). The reaction was stopped when the content of bromobenzene in the system was less than 5% and did not change with time after 2h of reaction by liquid chromatography. The post-processing operation was the same as that of Example 1, and dried to obtain sodium p-bromobenzene sulfinate (187.9 g, purity 97%) as a white solid powder |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With ammonium iodide In methanol at 40℃; for 2h; Schlenk technique; | 9 General experimental procedure for the synthesis of arylsulfonylated quinone derivatives (3) General procedure: Quinone 1 (0.2mmol), sodium arylsulfinate 2 (0.4mmol), and NH4I (0.8 mmol, 116 mg) in methanol (3.0 mL) were added to a 25mL Schlenk tube. The mixture was heated at 40 °C for 2.0 h (monitored by TLC). After completion of the reaction, the solvent was distilled under vacuum. 10mL ethyl acetate was added to the residuum, and 20 mL saturated sodium chloride solution washed two times. The organic phase was dried over anhydrous NaSO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired products 3 using ethyl acetate/petroleum ether (1:5 to 1:1) as eluant. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With water at 110℃; for 12h; Sealed tube; Green chemistry; | A typical procedure for the synthesis of aryl methyl sulfones General procedure: Sodium benzenesulfinate (0.5 mmol), 2-(tert-butylperoxy)-2-methylpropane (1 mmol), and H2O (2.5 mL) were added into a 10 mL sealed tube successively. Then, the reaction was carried out at 110 C under magnetic stirring for 12 h. After the reaction was finished, the reaction mixture was extracted with ethyl acetate for three times (5 mL × 3). The obtained organic layer was dried with anhydrous MgSO4. The solvent was removed under vacuum, and the obtained crude product was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10:1) as eluent to afford the desired pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With iodine In ethyl acetate at 20℃; for 16h; Schlenk technique; regioselective reaction; | General Procedure-1 (GP-1) for synthesis of N2-sulfonyl triazoles General procedure: A heat gun-dried Schlenk tube was charged NH-1,2,3-triazoles (1a-t, 5a and 5b, 0.4 mmol, 1 equiv.), sodium sulfinates (2a-d, 0.8 mmol, 2.0 equiv.) and I2 (111.7 mg, 0.44 mmol, 1.1 equiv.) in EtOAc (2.0 mL). The reaction mixture was stirred at room temperature for 8-24 h and monitored by TLC either complete or appeared to be proceeding no further progress. The mixture was quenched by addition of std. aqueous Na2S2O3 (10 mL) followed by extraction with EtOAc (3*10 mL). The combined organic layers was washed with H2O (2*10 mL), dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The resulting residue was subjected to flash chromatography (silica gel, eluted with 20% then 30% ethyl acetate/petether) to afford desired N-sulfonylated triazoles. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With iodine In ethyl acetate at 20℃; for 16h; Schlenk technique; regioselective reaction; | General Procedure-1 (GP-1) for synthesis of N2-sulfonyl triazoles General procedure: A heat gun-dried Schlenk tube was charged NH-1,2,3-triazoles (1a-t, 5a and 5b, 0.4 mmol, 1 equiv.), sodium sulfinates (2a-d, 0.8 mmol, 2.0 equiv.) and I2 (111.7 mg, 0.44 mmol, 1.1 equiv.) in EtOAc (2.0 mL). The reaction mixture was stirred at room temperature for 8-24 h and monitored by TLC either complete or appeared to be proceeding no further progress. The mixture was quenched by addition of std. aqueous Na2S2O3 (10 mL) followed by extraction with EtOAc (3*10 mL). The combined organic layers was washed with H2O (2*10 mL), dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The resulting residue was subjected to flash chromatography (silica gel, eluted with 20% then 30% ethyl acetate/petether) to afford desired N-sulfonylated triazoles. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With silver nitrate In ethanol at 80℃; for 12h; Inert atmosphere; | |
65% | With silver nitrate In ethanol at 80℃; for 12h; Schlenk technique; Inert atmosphere; | 16 Example 16 Synthesis of 3-(4-bromobenzenesulfonyl)-2-((4-(4-bromobenzenesulfonyl)phenyl)(phenyl)methyl)-1H-indole 0.3 mmol of 1H-indol-2-yldiphenylmethanol (the compound corresponding to the number (1), 0.0897 g) was weighed. 0.9 mmol of sodium 4-bromobenzenesulfinate (the corresponding compound of No. (17), 0.2177 g) and 0.6 mmol of silver nitrate (0.1019 g) in a 20 mL schlenk reaction tube. Add 2 mL of absolute ethanol as a solvent, protect with argon gas, and stir the reaction at 80 ° C for 12 hours; After the reaction is completed, column chromatography separation (column chromatography separation conditions: The stationary phase was 200-300 mesh silica gel, the mobile phase was ethyl acetate (A) and petroleum ether (B), and the mobile phase change procedure (A:B) was 1:5) to obtain 0.1400 g of the reaction product. According to the characterization data, the obtained reaction product is pure 3-(4-bromobenzenesulfonyl)-2-((4-(4-bromobenzenesulfonyl)phenyl)(phenyl)methyl)-1H-indole (purity > 95) %); Calculated for product yield, the result is 65%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dichloro bis(acetonitrile) palladium(II); silver(I) acetate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Schlenk technique; | General procedure for the synthesis of 3 General procedure: Under the argon atmosphere, a Schlenk tube (15 mL) equipped with a magnetic bar was loaded with the sulfonamide 1 (0.5 mmol), sodium arylsulfinates 2 (0.6 mmol, 1.2 equiv.), Pd(MeCN)2Cl2 (6.5 mg, 5 mol%) and AgOAc (166.9 mg, 1.0 mmol) in one portion. Then, the mixture of 1,4-dioxane/DMSO (3.5 mL in a 9:1 ratio) was added to obtain a clear solution and the reaction mixture was allowed to stir at 120 °C for 24 h. After cooling to room temperature, the mixture was filtered through a short celite pad and washed with dichloromethane (15 mL 3). The filtrate was concentrated and the oily crude product was purified by column chromatography using silica gel (200-300 mesh) as stationary phase and a petroleum ether and ethyl acetate (3/1) as eluent to give the N-aryl sulfonamides 3 in noted yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Stage #1: N,N-dimethyl-formamide With potassium <i>tert</i>-butylate In acetonitrile at 50℃; for 0.5h; Schlenk technique; Green chemistry; Stage #2: sodium 4-bromobenzenesulfinate With N-iodo-succinimide In acetonitrile at 50℃; for 12h; Schlenk technique; Green chemistry; | 2. General procedure for synthesis of sulfonamides from sodium sulfinates and formamides General procedure: An oven-dried Schlenk tube equipped with a magnetic stir bar was charged with formamide 1 (2.0 mmol), KO-t-Bu (2.0 mmol) and CH3CN (2.0 mL). The mixture was stirred at 50 °C for 30 min and then a CH3CN (2.0 mL) solution containing sodium sulfinates 2 (0.5 mmol) and NIS (1.0 mmol) was slowly added dropwise. The resulting solution stirred at 50 °C for 12 h under air. The mixture was then cooled to room temperature, diluted with 30 mL of H2O, and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium phosphate; N-Bromosuccinimide In dichloromethane at 20℃; for 24h; Schlenk technique; chemoselective reaction; | 17 4.2. General procedure for the decarboxylative sulfonylation reaction General procedure: A 25 mL Schlenk tube was charged with β-keto acids 2 (0.75 mmol), sodium sulfinates 3 (0.5 mmol), NBS (0.75 mmol), K3PO4 (0.75 mmol) and CH2Cl2 (3 mL). The mixture was stirred at room temperature for 24 h. After completion of the reaction, the solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography on silica gel to provide the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With bis(tri-tert-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; | 6 Embodiment 6This embodiment preparation of aryl three butyl tin compound as 4 - bromophenylacetic base three butyl tin, its synthetic method comprises the following steps: To 10 ml of the added long tubular reaction bottle 73 mg (namely 0.3 mmol) 4 - bromophenylacetic sulfinyl sodium, 3 mg (namely 0.006 mmol) b (tri-[...]) palladium, 83 mg (namely 0.3 mmol) silver carbonate and 2.0 ml N, N - dimethyl acetamide, then adding 116 mg (i.e. 0.2 mmol) six-butyl two Sn, in 140 °C lower reaction 1 h, concentration after the reaction, petroleum ether as eluant agent (mobile phase total 200 ml) column chromatography purification to obtain 4 - bromophenylacetic base three butyl tin.4 - Monobromo-benzene asia sodium sulfonate as the reactant, its structural formula is: B (tri-[...]) palladium as catalyst, its structural formula is: Pd (PtBu3)2, 4 - Bromophenylacetic base three butyl tin is the structural formula of:This embodiment the obtained product is colorless liquid, and the yield is 54%, |
54% | With bis(tri-t-butylphosphine)palladium(0); silver carbonate In N,N-dimethyl acetamide at 140℃; for 1h; Inert atmosphere; | 4) Typical procedure of desulfitative stannylation reactions General procedure: In nitrogen atmosphere, sodium benzenesulfinate (1a, 0.3 mmol, 1.5 equiv, 49 mg), Ag2CO3 (0.3 mmol, 1.5 equiv, 83 mg) and Pd(PtBu3)2 (0.006 mmol, 3 mol %, 3 mg) were weighed in a 10 mL reaction tube. N,N-Dimethylacetamide (2 mL), hexabutyldistannane (2a, 0.2 mmol, 1 equiv, 116 mg, 101 μL) were then added in succession. The resulting reaction solution was stirred for 1 h at 140 °C. The reaction system was filtered by siliga gel to remove the insoluble precipitate. The solution was concentrated under reduced pressure to evaporate the solvent, and then the crude product was purified by silica gel column chromatography (petroleum ether) to obtain tributyl(phenyl)stannane (3a) in 97% isolated yield (71 mg) as colorless liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With water; iodine; Dimethyl phosphite In ethyl acetate at 100℃; for 6h; Sealed tube; | |
71% | With water; iodine; Dimethyl phosphite In ethyl acetate at 100℃; for 6h; | 12 Example 12 Sodium p-bromobenzenesulfinate (0.2 mmol), iso-acetonitrile ethyl acetate (0.4 mmol), water (0.6 mmol), ethyl acetate (1.5 mL), molecular iodine ( 0.02 mmol), and dimethyl phosphite (0.4 mmol), mixed uniformly, and then stirred and reacted under a condition of 100 ° C for 6 h, and then detected by TLC. After completion of the reaction, 2 mL of water was added, followed by ethyl acetate. (4mL) extraction 3 times, the extract was concentrated under vacuum at 0.08Mpa under vacuum to give a crude product, then washed with a mixture of petroleum ether and ethyl acetate in a volume ratio of 5:1, silica gel column Chromatography gave thiocarbamate 71%, 44.9 mg white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dipotassium peroxodisulfate In water at 20℃; for 10h; Inert atmosphere; regioselective reaction; | II General Procedure for the Synthesis of 2-(phenyl sulfonyl) tetrahydrofuran 3: General procedure: A mixture of tetrahydrofuran 1 (1.0 mmol), sodium sulfinate 2 (1.0 mmol), K2S2O8 (1.5 equiv), and H2O (3 mL) was taken in a flask and stirred at rt for 8-12 h (Table 2). After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with ethyl acetate (3 × 5 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The resulting crude product was purified by silica gel chromatography using a mixture of hexane/ethyl acetate (4:1) as eluent to afford an analytically pure sample of product 3. Characterization data of compounds 3 are given below: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With copper(l) chloride In 1-methyl-pyrrolidin-2-one; water at 120℃; for 40h; Inert atmosphere; | 3.3. General Procedure for the Synthesis of N-Arylsulfonamides General procedure: A pressure tube (10 mL) was charged with CuCl (1.0 mg, 0.01 mmol), p-toluenesulfinic acid sodium salt (2a, 107.2 mg, 0.6 mmol), p-methyl nitrobenzene (1a, 27.4 mg, 0.2 mmol) and purged withargon three times. NMP (0.6 mL) and H2O (7.2 L) were added by syringe. The resulting solution was stirred at 120 C for 40 h. After cooling to room temperature, the crude product mixture was diluted with ethylacetate (15 mL) and washed with a saturated solution of NaCl (3 15 mL) and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 6:1) to give 3a as whitesolid; yield: 40.3 mg (77%) (NMR spectra for all compounds shown in Supplementary Materials). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dipotassium peroxodisulfate; oxygen In N,N-dimethyl-formamide at 100℃; for 12h; | General procedure for the synthesis of compounds 3: General procedure: A mixture of cinnamic acid 1 (1.0 mmol), K2S2O8 (1.5 mmol) and sodium sulfinate 2 (1.5 mmol) in DMF (5 mL) was stirred at 100 oC under ambient air for 12 h. Upon completion of the reaction (monitored by TLC), the mixture was extracted with EtOAc (3 x 15 mL). The combined organic phase was dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (EtOAc/n-hexane, 1:4) to afford an analytically pure sample of β-keto sulfones 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With hydrogen iodide In toluene at 75℃; for 15h; | 3.1 1) Preparation method of compound 3: 0.3 mmol (0.0541 g) of 1,1-diphenylethylene , 0.45 mmol (0.1094 g) of sodium p-bromobenzenesulfinate, and 0.2558 g of a 45% aqueous hydroiodic acid solution (containing 0.9 mmol of hydroiodic acid) Disperse in 2mL of toluene, conduct coupling reaction at 75 ° C for 15h, add saturated sodium thiosulfate aqueous solution for quenching, extract with dichloromethane (15mL × 3), separate the layers, and dry the organic with anhydrous sodium sulfate Layer, spin-dried under reduced pressure, and passed through the column to obtain 0.0895 g of distyryl sulfide compound (white solid, yield 81%, |
81% | With hydrogen iodide In toluene at 75℃; for 15h; | 7 Example 7 A method for preparing a distyryl sulfide compound, comprising the steps of:0.3mmol (0.0541g)1,1-stilbene, 0.45 mmol (0.1094 g) of sodium p-bromobenzenesulfinate and 0.2558 g of a 45% by mass aqueous solution of hydroiodic acid (containing 0.9 mmol of hydroiodic acid) were dispersed in 2 mL of toluene. The coupling reaction was carried out at 75 ° C for 15 h, quenched with a saturated aqueous solution of sodium thiosulfate, and extracted with dichloromethane (15 mL×3).The liquid layer was separated, and the organic layer was dried over anhydrous sodium sulfate.Dry under reduced pressure, and the column was passed to give 0.0895 g of distyryl thioether compound (white solid, yield 81%, |
81% | With hydrogen iodide In water; toluene at 75℃; for 15h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Sealed tube; | 15 Example 1 General procedure: (1) 1 mmol of a polyfluoro-substituted peroxy compound (0.4123 g), 3 mmol of an organic sulfinate (0.4925 g), and 5.5 mmol of an alkali promoter (1.7920 g) are added to a 10 mL test tube reaction tube. Add 2 mL of tert-butanol as a solvent to the reaction tube, seal it tightly, and stir the reaction at 50 ° C for 24 hours. Among them, the polyfluoro substituted peroxy compound is 1- (tert-butylperoxy) -2-perfluorobutyl ethyl Benzene, organic sulfinate is sodium benzenesulfinate; base accelerator is cesium carbonate;(2) After the reaction in step (1), the reaction solution is sequentially dried with water, ethyl acetate, anhydrous sodium sulfate, and column chromatography (column chromatography separation conditions: the stationary phase is 300-400 mesh silica gel powder, The mobile phase was ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A: B) was 1: 20 → 1: 3. 0.4014 g of reaction product 1 was obtained.Characterization of the above reaction products, the results were: white solid;According to the characterization data, it can be known that the prepared reaction product 1 is 2- (perfluoroethyl) -5-phenyl-3,4-bisphenylsulfone furan (purity> 95%); the product yield is calculated. The result was 74%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With lithium hydroxide In <i>tert</i>-butyl alcohol at 50℃; for 24h; Sealed tube; | 28 Example 1 General procedure: (1) 1 mmol of a polyfluoro-substituted peroxy compound (0.4123 g), 3 mmol of an organic sulfinate (0.4925 g), and 5.5 mmol of an alkali promoter (1.7920 g) are added to a 10 mL test tube reaction tube. Add 2 mL of tert-butanol as a solvent to the reaction tube, seal it tightly, and stir the reaction at 50 ° C for 24 hours. Among them, the polyfluoro substituted peroxy compound is 1- (tert-butylperoxy) -2-perfluorobutyl ethyl Benzene, organic sulfinate is sodium benzenesulfinate; base accelerator is cesium carbonate;(2) After the reaction in step (1), the reaction solution is sequentially dried with water, ethyl acetate, anhydrous sodium sulfate, and column chromatography (column chromatography separation conditions: the stationary phase is 300-400 mesh silica gel powder, The mobile phase was ethyl acetate (A) and petroleum ether (B), and the mobile phase change program (A: B) was 1: 20 → 1: 3. 0.4014 g of reaction product 1 was obtained.Characterization of the above reaction products, the results were: white solid;According to the characterization data, it can be known that the prepared reaction product 1 is 2- (perfluoroethyl) -5-phenyl-3,4-bisphenylsulfone furan (purity> 95%); the product yield is calculated. The result was 74%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With dipotassium peroxodisulfate; silver nitrate In water; dimethyl sulfoxide at 100℃; for 24h; Sealed tube; Inert atmosphere; | 2. Typical procedure for the synthesis of 3-((phenylsulfonyl)methyl)chroman-4-one General procedure: A sealable reaction tube equipped with a magnetic stirrer bar was charged with 2-(allyloxy)benzaldehyde (0.2 mmol), Sodium benzene sulfinate (2.0 equiv.), AgNO3 (20 mol%), K2S2O8 (3.0 equiv.), DMSO:H2O=1:1 (2 ml). The reaction vessel was carried 100. After completion, it was diluted with ethyl acetate, washed with water. After the solvent was removed under reduced pressure, the residue was purified by column chromatography on silica gel to afford the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; copper(II) bis(trifluoromethanesulfonate); dibutyl phosphate In 1,2-dimethoxyethane; acetonitrile at 20℃; for 12h; Inert atmosphere; Sealed tube; Glovebox; Irradiation; | Typical procedure for decarboxylative sulfonylation General procedure: An oven-dried 15 mL sealed tube equipped with a Teflon-coated magnetic stir bar was sequentially charged with 1,3-dioxoisoindolin-2-yl 4-phenylbutanoate (1a) (62mg, 0.20 mmol), sodium p-toluenesulfinate (71 mg, 0.40 mmol), 4CzIPN (3.2 mg,0.004 mmol), Cu(OTf)2 (14.5 mg, 0.04 mmol) in a glove box. Next, DME (1.0 mL),MeCN (1.0 mL) and (BuO)2P(O)OH (84 mg, 79 uL, 0.40 mmol) was added into the tube under nitrogen atmosphere. The tube was then placed 3 cm away from a 3 W blue LED and the mixture was stirred at room temperature for 12 h. An electric fan was placed close to the tube (see Figure S2) to cool down the reaction mixture (the internal temperature of the tube was measured to be around 30 oC). After the removal of solvent, the residue was purified by column chromatography on silica gel with a gradient eluent of petroleum ether and ethyl acetate to provide the pure product 1-methyl-4-((3-phenylpropyl)sulfonyl)benzene (3a) as a white solid. Yield: 50 mg (92%yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 25℃; for 0.5h; | General procedure for the preparation of sulfoxides 4. General procedure: The mixture of asodium arylsulfinate (0.2 mmol, 1.0 equiv), a pyrrole/thiophene (0.3 mmol, 1.5equiv) and TMSOTf (0.4 mmol, 2.0 equiv) in (ClCH2)2 (1.0 mL) was stirred at25 °C for 0.5 h, then water (5 mL) and dichloromethane (10 mL) were added.The two layers were separated, and the aqueous phase was extracted withdichloromethane (3 × 10 mL). The combined organic extracts were washed bybrine, dried over anhydrous Na2SO4, filtered, and concentrated. The residuewas purified by flash chromatography on silica gel (ethyl acetate : petroleumether = 1:1) to afford the desired sulfoxides 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(I) oxide; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h; Sealed tube; | General Procedure for synthesis of non-chiral benzylic sulfones General procedure: To an oven-dried 25 mL test tube with standard ground joint equipped with a stir bar were added a quaternary ammonium salt of benzyl tertiary amine, Cu2O (0.1 mmol), K2CO3 (1.0 mmol), Sodium sulfinate (2.0 mmol), and dmf (4 mL) were added to the test tube. After the test tube was sealed with a sleeve rubber stopper, the mixture was stirred at 120 °C for 24h. After cooled to room temperature, the reaction mixture was quenched by the addition of saturated NaCl solution (10 mL). The reaction mixture was extracted with ethyl acetate (15 ml×3). The combined organic phase was dried over MgSO4, filtered and concentrated in vacuum on a rotary evaporator. The resulting residue was purified by silica gel flash chromatography, eluting with petroleum ether/EtOAc (5%-40% EtOAc), to afford the corresponding products 3 as a white or yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With iron(II) chloride In N,N-dimethyl-formamide at 80℃; for 8h; | 16 Example 16 Add 0.5 mmoles of 3-methylbenzisoxazole,0.6 mmol sodium 4-bromobenzenesulfinate, 0.05 mmol ferrous chloride and 2 mL DMF were sequentially added to a 25 mL screw test tube, stirred at 80°C for 8 hours, and cooled to room temperature after the reaction. Filter, take the filtrate, and remove the solvent by rotary evaporation under reduced pressure to obtain the crude product. The crude product is purified by column chromatography to obtain the product 3ap with a yield of 73% and a purity of 98%. |
64% | With water; iron(II) chloride at 80℃; for 8h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sulfuric acid; triphenylphosphine In water; acetonitrile at 80℃; for 3h; Schlenk technique; Inert atmosphere; | 7 Example 7 Combine 121.0 mg (0.5 mmol) of 4-bromobenzenesulfinate sodium, 176.4 mg (0.6 mmol) of 4-phenylmethylene-2,6-di-tert-butyl-2,5-cyclohexadien-1-one , 1.0 mmol of triphenylphosphine, 1.0 mmol of sulfuric acid, add to the Schlenk tube under nitrogen, add 1.0 mL of acetonitrile and 1.0 mL of water under nitrogen, stir and react at 80 oC for 3 hours. After the reaction is completed, the product is separated and purified by column chromatography, and the yield of the target product is 86%. |
86% | With sulfuric acid; triphenylphosphine In water; acetonitrile at 80℃; for 3h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With dipotassium peroxodisulfate; iodine In water; acetonitrile at 20℃; for 24h; | 3.General procedure for the synthesis of compounds (3a-3q): General procedure: A mixture of 2,9,9-trimethyl-5-methylene-6,7,8,9-tetrahydro-5H-benzo[7]annulene (0.25 mmol, 1.0 equiv.), sodium benzenesulfinate (0.3 mmol, 1.2 equiv.), K2S2O8 (0.62 mmol, 2.5 equiv.), and I2 (0.3 mmol, 1.2 equiv.), in ACN:H2O (1:1) were placed in reaction tube (5 mL) at room temperature for 12 h. After completion of reaction the saturated solution of sodium thiosulfate was added to the reaction mixture and extracted with ethyl acetate (10 X 3 times). The combined organic layer was washed with water and dried over Na2SO4 and vacuum evaporated. The viscous liquid obtained which was purified by column chromatography on silica gel (mesh 60-120) using the mixture of (hexane: EtOAc = 80:20) to obtained the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With 3-chloro-benzenecarboperoxoic acid In toluene at 80℃; for 15h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With copper(II) bis(trifluoromethanesulfonate) In ethanol at 60℃; for 4h; | General procedure for the preparation of b-keto sulfones 3 General procedure: A mixture of vinyl azides 1(0.2mmol), sodium sulfinates 2(0.4mmol) andCu(OTf)2 (20mol%) in EtOH (2 mL) was stirred at 60 C in a reaction tube for 4 h. After the reaction is over, concentrated and purified by chromatography (petroleum ether/ethylacetate = 4:1) on silica gel to afford the desired products β-keto sulfones. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With pentacene-5,7,12,14-tetraone; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 31h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With pentacene-5,7,12,14-tetraone; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 31h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | In dimethyl sulfoxide at 25℃; for 12h; Inert atmosphere; | General synthetic procedure A: General procedure: To a test tube was added 1-(4-ethynylphenyl)ethan-1-one 1(0.2 mmol, 1.0 equiv.), trifluoromethyl thianthrenium triflate 2(0.4 mmol, 2.0 equiv.) and sodium sulfinate 3 (0.4 mmol, 2.0 equiv.).Then the tube was purged with argon for 3 times. DMSO (2.0 mL)was added by a syringe and the tube was stirred at 25 C for 12 h.After the scheduled time, the mixture was quenched with waterand extracted with EtOAc (20 mL * 3). The combined organic phaseswere washed with brine and dried over anhydrous Na2SO4. The solvent was then evaporated under reduced pressure and the residuewas purified directly by flash column chromatography toafford the corresponding product 4 as white solids. |
Tags: 34176-08-4 synthesis path| 34176-08-4 SDS| 34176-08-4 COA| 34176-08-4 purity| 34176-08-4 application| 34176-08-4 NMR| 34176-08-4 COA| 34176-08-4 structure
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