| 98% |
With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.75h; |
General procedure: In this step, to mixture of sulfide (1mmol) and H2O2 (0.4mL), SBA-15(at)serine(at)Pd catalyst (0.004g) was added and the reaction mixture was stirred at room temperature under solvent-free condition for appropriate time. Then, the completion of the reaction progress monitored by TLC with n-hexane solvent. Then, catalyst was filtered and washed with ethyl acetate to give the pure sulfoxides in good to high yields. |
| 97% |
With urea hydrogen peroxide adduct; In ethanol; at 20℃; for 2.33333h; |
General procedure: To the mixture of sulfide (1 mmol) and catalyst (20 mg) in ethanol (4 mL), UHP was added (7 mmol). The reaction mixture was stirred at room temperature for the appropriate time until TLC indicated the reaction was complete. The product was extracted with ethanol (10 mL), dried over anhydrous Na2SO3, and then concentrated to get an analytically pure product. |
| 97% |
With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.25h;Green chemistry; |
General procedure: A mixture of sulfide (1 mmol), hydrogen peroxide (1.2 mmol) and Br3-Fe3O4 (0.005 g, 0.01 mmol) was stirred at room temperature under solvent-free condition and the progress of the reaction was monitored by TLC. After completion of the reaction, catalyst was separated by external magnet and washed with ethyl acetate, and next, the product was extracted with ethyl acetate (5 mL × 4). The organic layer was dried over anhydrous Na2SO4 (1.5 g). Finally, the organic solvents were evaporated, and products were obtained in good to high yield. |
| 97% |
With dihydrogen peroxide; In ethyl acetate; at 20℃; for 0.416667h; |
General procedure: A mixture of sulfide (1 mmol), H2O2 (0.4 mL) and boehmite-SSA (0.003 g) in ethyl acetate (2 mL) was stirred at room temperature (the progress of the reaction was monitored by TLC). After completion of the reaction, catalyst was separated using filtration and washed with ethyl acetate,and the product was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 (1.5 g).Finally, ethyl acetate was evaporated, and product obtained in good to high yield. |
| 97% |
With dihydrogen peroxide; In water; at 20℃; for 0.833333h;Catalytic behavior; |
General procedure: In a typical reaction, organic substrate (5 mmol) was added to a solution of catalyst [PAMo (3.44 mg) or PSMo (4.9 mg), containing 0.005 mmol of Mo] and 30% H2O2 (2.26 mL, 20 mmol) in 5 mL of water. The molar ratio of substrate: H2O2 and that of catalyst (Mo): substrate was maintained at 1: 4 and 1: 1000, respectively. The reaction was conducted at room temperature under magnetic stirring. The reaction progress was monitored by thin layer chromatography (TLC) and GC. After completion, the product and unreacted organic substrates were extracted with diethyl ether, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove excess solvent. The crude product obtained was purified by column chromatography on silica gel with ethyl acetate- hexane (1: 9 v/v) as the eluent. |
| 97% |
With dihydrogen peroxide; at 20℃; for 0.25h;Green chemistry;Catalytic behavior; |
General procedure: 0.008 g of Ni-dithizoneboehmite was added to a solutionof sulfide (1.0 mmol) and 0.4 mL of H2O2(33%). Theobtained mixture was stirred under solvent-free conditions at room temperature for the specified times (Table 4) andthe progress of the reactions was monitored by TLC inn-hexane:acetone solution (volume ratio, 8:2). After completionof the reaction, the catalyst was separated by simplefiltration. The products were extracted with water and ethylacetate, and dried over anhydrous Na2SO4.Then, the solvent was evaporated and pure products were obtained in high toexcellent yields. |
| 97% |
With dihydrogen peroxide; In water; at 0℃; for 1.5h;Green chemistry;Catalytic behavior; |
General procedure: In a representative procedure, to a solution of a catalyst(0.002 mmol) in water (5 mL) organic substrate (5 mmol)was added maintaining a catalyst:substrate molar ratio of1:2500. The oxidant, 30% H2O2 (1.13 mL, 10 mmol) was then added to it (substrate:H2O2 ratio of 1:2). The reactionwas conducted at 0C in an ice bath under continuous magneticstirring. The progress of the reaction was monitored bythin-layer chromatography (TLC) and GC. After completionof the reaction, the products were extracted with diethyl etherand dried over anhydrous Na2SO4 and distilled under reducedpressure to remove excess diethyl ether. The correspondingsulfoxide obtained was purified by column chromatographyon silica gel using ethyl acetate and n-hexane(1:9). The products obtained were characterized by IR, 1HNMR, and 13C NMR spectroscopy, and in the case of solidsulfoxides products, in addition to the above spectral analysis,we have also carried out melting point determination [seeText S1 (Supplementary information)]. |
| 95% |
With urea hydrogen peroxide adduct; In ethanol; at 20℃; for 23h; |
General procedure: To examine the catalytic activity of Cr-MCM-41 and Mn-MCM-41, we studied catalytic oxidation of several types of alkyl and aryl sulfides to corresponding sulfoxides at room temperature (Scheme 2). A mixture of sulfides (1 mmol), UHP (5 mmol), and Cr- or Mn-MCM-41 (25 mg) was stirred in ethanol at room temperature, and the progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the catalyst was separated by simple filtration and washed with dichloromethane (3 9 10 mL). The results arepresented in Table 4. |
| 95% |
With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane; In tetrahydrofuran; at 20℃; for 0.2h;Green chemistry; |
General procedure: To a stirred solution of sulfde (1 mmol) and THF (4 mL),THPDPE (1 up to 5.5 mmol (0.310 up to 1.70 g) dependingon the substrates and products) was added and the mixture wasstirred at room temperature for an appropriate time. After completion of the reaction, as monitored by TLC, a saturated aqueous solution of Na2SO3 (2 mL of 1 M solution) was added toquench the excessive oxidant that was remained in the mixture.Water (10 mL) was added to the mixture and extracted usingchloroform (3 × 5 mL) and dried over anhydrous MgSO4. Afterevaporation of solvent under reduced pressure chromatographyon silica gel was used to give pure products. |
| 95% |
With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.0333333h; |
General procedure: A mixture of sulfide (1 mmol), H2O2(0.5 mL) and MCM-41(at)Tryptophan-M (Cd or Hg) (0.005 g) was stirred underneat conditions at room temperature for appropriate time andthe progress of the reaction was monitored by TLC. Aftercompletion of the reaction, the catalyst was separated byfiltration and washed with ethyl acetate. Finally, ethyl acetatewas evaporated, and then pure product with excellent yieldwas obtained by crystallization from ethanol (Scheme 2). |
| > 95% |
With dihydrogen peroxide; In water; at 20℃; for 0.0833333h; |
General procedure: The sulfide (1 mmol) was added to a mixture of 30% H2O2 (3.6 mmol) and MNPs-PhSO3-Sc(OTf)2 (25 mg), and the mixture was then stirred at room temperature for the time specified. The progress of reaction was monitored by TLC (EtOAc/n-hexane, 3/10). After completion of the reaction, the catalyst was separated from the reaction mixture by an external magnet and the mixture was decanted. The product was extracted with Et2O (2×5 mL) and the combined organic phases were washed with brine (10 mL) and dried over anhydrous Na2SO4. The evaporation of solvent under reduced pressure gave the pure products in 90-98% yields. All the products were known and characterized by comparison of their 1H NMR spectra and physical properties (melting point) with those of authentic samples [19-22]. |
| 95% |
With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.166667h;Green chemistry;Catalytic behavior; |
General procedure: 0.008 g (0.17 mol %) of Cu-Adenineboehmite was added to asolution of sulfide (1 mmol) and 0.4 mL of H2O2 (33%), the mixturewas stirred under solvent free conditions at room temperature forthe specified time (Table 6) and the progress of the reaction wasmonitored by TLC. After completion of the reaction, the catalystwas separated by simple filtration. The product was extracted withwater and ethyl acetate and dried over anhydrous Na2SO4 (1.5 g).Then, the solvent was evaporated and pure products were obtainedin high yields. |
| 94% |
With (pyridinium)H3PMo11VO40; dihydrogen peroxide; In water; acetonitrile; at 20℃; for 0.5h; |
General procedure: The oxidation of methyl phenyl sulfide to methyl phenyl sulfoxide or methyl phenyl sulfone (Scheme 1) was typically carried out bystirring a solution of 0.7 mmol of the substrate and 0.01 mmol of the catalyst in 5 mL of acetonitrile, at 20 or 40 C, respectively. Theoxidant used was H2O2 35% in aqueous solution (2 or 20 mmol,respectively). The sample was collected from the reaction mixtureduring the reaction at time intervals. About 20 muL of the reactionmixture was taken for each sample, which was then diluted in amixture of water-dichloromethane (2 mL). The dichloromethanelayer was dried with anhydrous sodium sulfate and filtered. GC/MSanalyses were performed on an HP 5971 mass detector coupled to anHP gas chromatograph fitted with a 30 m×0.25 mm DB5 capillarycolumn. The percentages of each compound in the reaction mixturewere directly estimated from the corresponding chromatographicpeak areas. The yield (%) of pure sulfoxide or sulfone, the turnovernumber (TON: product mol×catalyst mol-1) and turnover frequency(TOF: product mol×catalyst mol-1×h-1) were also calculated. Under these optimum conditions and using M11PV1Py1 ascatalyst, different sulfides were oxidized to sulfoxides (for 30 min)and to sulfones (for 2.5 and 3.5 h) depending on the substrate. |
| 94% |
With dihydrogen peroxide; In neat (no solvent); at 35℃; for 0.0833333h;Green chemistry; |
General procedure: A mixture of sulfide (1 mmol), H2O2 (0.4 mL) and M-Salen-MNPs (0.02 g) was stirred at 35 C under solvent-free conditionand the progress of the reaction was monitored by TLC. After completion of the reaction, catalyst was separated using external magnet and washed with ethyl acetate, and next, the product wasextracted with ethyl acetate. The organic layer was dried overanhydrous Na2SO4 (1.5 g). Finally, the organic solvents were evaporated,and products were obtained in good to high yield. |
| 94% |
With urea-2,2-dihydroperoxypropane; In tetrahydrofuran; at 20℃; for 0.216667h;Green chemistry; |
General procedure: To a stirred solution of sulfide (1 mmol, 0.124 g) and THF (4 mL), urea-2,2-dihdroperoxypropane (2 or 6 mmol, 0.336-1.00 g pending to products) was added and the mixture was stirred at room temperature for an appropriate time. After completion of the reaction as monitored by TLC, saturated aqueous solution of Na2SO3 (2 mL of 1 M solution) was added to quench the excessive oxidant remaining in the mixture. Then water (10 mL) was added to the mixture and extracted using chloroform (3 × 5 mL) and dried over anhydrous MgSO4. After evaporation of solvent under reduced pressure, chromatography on silica gel was used to give pure products. |
| 94% |
With dihydrogen peroxide; In water; at 20℃; for 0.8h;Green chemistry; |
General procedure: In this study, as a typical procedure, hydrogen peroxide solution (0.5 mL) was added to suspension of sulfide (1 mmol) and Fe3O4/AMPD/Ni (0.005 g) in a round-bottomed flask, and the mixture was stirred under solvent-free condition at room temperature for an appropriate time period. After completion of the reaction [monitored by thin-layer chromatography (TLC)], the catalyst was removed by means of a magnet to be reused in subsequent reactions and washed with ethyl acetate to obtain the pure sulfoxides. |
| 94% |
With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.666667h;Green chemistry; |
General procedure: Sulfide (1 mmol), H2O2 (0.4 mL) and SBA-15atAMPD-Co nanocatalyst (7 mg) were vigorously stirred in a round-bottomed flask at room temperature in solvent-free conditions for an appropriate time. To investigate the completed reaction, TLC (EtOAc/nhexane,1:10) was used. When the reaction was finished, the catalyst was separated by filtration and the products were extractedwith H2O and CH2Cl2. Afterward, the combined organics were dried over anhydrous Na2SO4. Evaporation of the solvent gave the pure corresponding sulfoxides in good to high yield (86-97%). |
| 94% |
With dihydrogen peroxide; In water; at 20℃; for 1.25h;Catalytic behavior; |
General procedure: In a representative procedure, the organic substrate MPS (5mmol) was added to the reaction mixture consisting of the catalyst (21.00mg, containing 0.005mmol of V) in 5mL of H2O. Then 30% H2O2 (2.82mL, 25mmol) was added to the reaction system, contained in a round bottom flask. The molar ratio of V:substrate and that of substrate:H2O2 was maintained at 1:1000 and 1:5, respectively. For the reaction conducted in acetonitrile, the V:substrate and the substrate:H2O2 ratios were adjusted to 1:1000 and 1:2, keeping the other reaction conditions identical to the reaction conducted in water. The reaction was conducted at ambient temperature under continuous magnetic stirring. The progress of the reaction was monitored by thin layer chromatography (TLC) and GC. After completion of the reaction, the catalyst was separated by filtration and washed with acetone. The product and the unreacted substrates were extracted with diethyl ether from the filtrate, dried over anhydrous sodium sulphate and distilled under reduced pressure to remove excess solvent. The obtained product was purified by column chromatography on silica gel using ethyl acetate-hexane (1:9) as the eluent. The product was characterized by IR, 1H NMR, 13C NMR and melting point determination for solid products [Text S1 (Supplementary Information)]. |
| 94% |
With dihydrogen peroxide; In water; at 20℃; for 1.16667h;Green chemistry;Catalytic behavior; |
General procedure: In a typical procedure, the sulfide oxidation reaction was carried out by placing organic substrate (5 mmol), catalyst containing 0.005 mmol of Ti [PATi (1.40 mg) or PMATi (1.88 mg)], 30% H2O2 (2.26 mL, 20 mmol) in 5 mL of water in a round bottom flask. The molar ratio of Ti: substrate was maintained at 1:1000 and substrate: H2O2 at 1:4. Reaction was conducted at ambient temperature under magnetic stirring. The progress of the reaction was monitored by thin layer chromatography (TLC) and GC. After completion of the reaction, the oxidized product along with unreacted organic substrate were extracted with diethyl ether, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove excess diethyl ether. The product was then purified by column chromatography on silica gel with ethyl acetate-hexane (1: 9 v/v) as the eluent. The product obtained was characterized by IR, 1H NMR, 13C NMR spectroscopy and melting point determination (for solid products) [Text S1 (Supporting Information)]. |
| 93% |
With urea hydrogen peroxide adduct; In ethanol; at 20℃; for 18h; |
General procedure: To a mixture of sulfides (1 mmol) and the catalysts (25 mg) inEtOH(4 mL),UHP (5 mmol) was added, and the resulting reactionmixture was stirred at room temperature for the specifiedtime (Table 4). After completion of the reaction, the catalyst wasremoved by simple filtration and the resulting products were filteredand washed with dichloromethane (3 × 10 mL). |
| 93% |
With dihydrogen peroxide; In neat (no solvent); at 20℃; for 1h;Green chemistry; |
General procedure: A mixture of sulfide (1 mmol) and H2O2(0.4 mL) in solvent-free conditions was stirred for an appropriate time atroom temperature in the presence of MCM-41XANi(II)(0.01 g). After completion of the reaction, ethylacetate wasadded to the reaction mixture and the insoluble catalyst wasfiltered. The filtrate washed with water (5 mL) and dried over anhydrous Na2SO4.Then, the organic medium wasremoved under reduced pressure to give the correspondingpure sulfoxide in high to excellent yield. |
| 93% |
With 1,1?-(butane-1,4-diyl)bis(1,4-diazabicyclo[2.2.2]octane-1,4-diium) bis(hydrogen sulfate) dinitrate; potassium bromide; In neat (no solvent); at 20℃; for 0.283333h;Green chemistry; |
General procedure: A mixture of an sulfide (1 mmol), [C4(DABCO-H)2]·[HSO4]2[NO3]2(0.5 mmol) and KBr (0.05 mmol) was vigorously grind using a mortarand pestle at roomtemperature. After completion of the reaction (monitoredby TLC), 5 mL water was added to the mortar and the mixturewas filtered to separate the nitrated product. The products were purifiedwith short column chromatography. |
| 93% |
With dihydrogen peroxide; In water; at 20℃; for 0.333333h; |
General procedure: A mixture of Fe3O4MCM-41VO-SPATB (10 mg), sulfide (1 mmol) and 33 % H2O2 (0.4 mL) was stirred atambient temperature under solvent-free conditions for the specified time, and the progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, water was added to the reaction mixture, the catalyst was separated by an external magnet and the product was extracted with ethyl acetate (3 × 10 mL), and then dried over anhydrous Na2SO4(1.5 g). Finally organic solvent was evaporated, and sulfoxides were obtained in good-to-high yields |
| 91% |
With dihydrogen peroxide; In water; acetonitrile; at 20℃; for 0.416667h; |
General procedure: A mixture of benzyl phenyl sulfide (1 g, 5.0 mmol), silica vanadic acid (5 mg, 0.039 mmol of V) and H2O2 30% (6 mmol) in CH3CN (3 mL) was stirred for 10 min. After completion of the reaction, solvent was evaporated and the product was extracted with ether (2× 10 mL), dried with anhydrous Na2SO4, filtered and evaporated to afford the crude sulfoxide product. Finally, the product was purified by column chromatography using ethyl acetate/hexane (1.5:8.5) as eluent to give benzyl phenyl sulfoxide as a white solid in 93% yield. |
| 91% |
With dihydrogen peroxide; In neat (no solvent); at 20℃; for 0.5h; |
General procedure: To prepare the sulfoxide from the desired sulfide, 1 mmol ofsulfide, 0.3 mL of hydrogen peroxide 33% and 0.005 g of synthesized nanocatalyst were added to the test tube. The mixture was stirred until the sulfoxide was produced. The reaction completion was monitored by thin layer chromatography (TLC). The magnetic nanocatalyst was separated from the reaction by a magnetic field, and then the reaction mixture was washed with EtOAc. After evaporation of the excess solvent, the yields of the synthesized products were measured. |
| 91% |
With dihydrogen peroxide; In water; at 20℃; for 0.75h;Green chemistry; |
General procedure: In order to examine the catalytic activity of catalyst, Fe3O4MCM-41Ni-P2C (10 mg) were added to solution of sulfide (1 mmol) and 33% H2O2 (0.4 mL) under solvent free conditions, the mixture was stirred at room temperature for the specified time, and the progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, water was added to the reaction mixture, the catalyst was separated by an external magnet and the product was extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 (1.5 g), then organic solvents were evaporated, and sulfoxides were obtained in good to high yield. |
| 90% |
With tert.-butylhydroperoxide; [Mo2(O)4[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2]; In 1,2-dichloro-ethane; for 0.0833333h;Reflux; |
General procedure: In a 25 mL round-bottom flask equipped with a magnetic stirring bar, a solution of sulfide (1 mmol), catalyst (6 mg, 0.008 mmol, 0.016 mmol Mo) in 1,2-dichloroethane (4 mL) was prepared. TBHP (2 mmol) was added to this solution and the reaction mixture was stirred under reflux conditions. The reaction progress was monitoredby TLC. After the reaction was completed, the isolation and purification of the products were done as described above. |
| 90% |
With choline chloride; dihydrogen peroxide; toluene-4-sulfonic acid; In ethanol; at 40℃; for 1h;Green chemistry; |
General procedure: A mixture of benzyl phenyl sulfide (0.2 g, 1 mmol), 30% H2O2 (2 mmol), ethanol (3 mL) and ChCl/p-TsOH (20 mol%, four drops) was stirred at 40C for 1 h (monitored by TLC). After completion of the reaction, the reaction mixture was extracted with EtOAc (3×5 mL). The organic layer was concentrated and the resulting crude product was further purified by column chromatography on silica gel with petroleum ether/EtOAc as eluent, providing the sulfoxide 2a in 95% yield. The DES was then readily recovered via evaporation under vacuum at 80C and reused for the next cycle. All the products are known compounds and fully characterised. |
| 90% |
With dihydrogen peroxide; In acetonitrile; at 20℃; for 2h; |
General procedure: To a solution of sulfide (1 mmol) and 30% H2O2 (3 equivalent) in CH3CN (10 mL), catalyst I (0.189 g, 3 mol% Mo) was added and the mixture was stirred at room temperature for the time specified. Completion of the reaction was indicated by Thin Layer Chromatography (TLC) (n-hexane/ethylacetate 3.5:1) and GC. After completion of the reaction, Et2O was added and the catalyst was separated by a small magnet placed at the bottom of the flask. Finally, the excess of solvent was removed under reduced pressure to give the corresponding pure sulfoxide. Further purification was achieved by chromatography on silica gel with n-hexane/ethylacetate. All reaction products were identified by GC chromatogram, IR spectra and melting point as compared with authentic samples. |
| 89% |
With dihydrogen peroxide; In neat (no solvent); at 20℃; |
General procedure: In order to examine the catalytic activity of the catalyst, asolution of sulfide (1 mmol) and MCM-41SerineCu(II)(3 mg) was added to the round-bottomed flask containinghydrogen peroxide solution (0.5 mL) under solvent-free condition.The mixed reaction was stirred at room temperaturefor a time period. After completion of the reaction (monitoringby TLC), MCM-41SerineCu(II) catalyst was easilyseparated by filtration, and then the product extracted withethyl acetate and dried over anhydrous Na2SO4to give thepure sulfoxide. |
| 88% |
With phosphovanadomolybdic acid; dihydrogen peroxide; In acetonitrile; at 25℃; for 0.916667h; |
General procedure: A solution of sulfide (1 mmol) and catalyst (0.01 mmol), in acetonitrile, was addedto 35% (w/v) H2O2 (2 mmol). The mixture was stirred at 25C for a time period (seeTables 1 and 2). The solvent was evaporated and then H2O (5 mL) was added. The substratewas extracted with toluene (2 × mL) and dried with anhydrous Na2SO4; filtration andevaporation afforded the corresponding crude sulfoxides. The solids were purified byrecrystallization to afford the pure sulfoxides. The products were confirmed by 1H NMRand 13C NMR analyses |
| 87% |
With 2C8H15N2(1+)*Mo6O19(2-); dihydrogen peroxide; In methanol; at 25℃; for 0.75h;Schlenk technique; Inert atmosphere; |
General procedure: Catalyst (20 mmol) and sulfide (2 mmol) were dissolved in MeOH (1 mL), followed by dropwise addition of H2O2 (35%) (0:19 mL, 2:1 mmol) at room temperature. The progress of the reaction was followed by TLC. After completion of the reaction, 3 mL of ethyl acetate was added to the mixture to obtain the catalyst by filtration. The solvent was removed under vacuum for 4 h and then the crude products were analyzed by GLC or 1H NMR using internal standard technology The sulfoxides were purified by column chromatography (silica gel using hexane-ethyl acetate 90 : 10v=v). For the recycling experiment, ethyl acetate was added to the reaction mixture after the reaction was completed and the catalyst precipitated, filtered off, washed with ethyl acetate, and dried in high vacuum at room temperature. All products were characterized by melting point, 1H NMR, 13CNMR and IR spectroscopy (see Supporting Information). |
| 87% |
With dihydrogen peroxide; In ethanol; at 20℃; for 0.166667h;Green chemistry; |
General procedure: The catalyst (0.010 g) was added to solution of sulfide (1 mmol) and H2O2 (0.5 mL) in ethanol (2 mL). The reaction mixture was stirred at room temperature, and the progress of the reaction was monitored by TLC (acetone:n-hexane, 2:8). After completion of the reaction, catalyst was separated by an external magnet and washed with ethyl acetate; next, the product was extracted with ethyl acetate (5 mL 9 4). The organic layer was dried over anhydrous Na2SO4 (1.5 g). Finally, the organic solvents were evaporated, and the corresponding sulfoxides were obtained in high to excellent yields (88-99%). |
| 86% |
With dihydrogen peroxide; In methanol; at 20℃; for 1.25h; |
General procedure: To a stirred suspension of the selected sulfide (1 mmol) and the heterogeneous catalyst PW12(at)Al-MCF (3 mol%) in methanol (5 ml), H2O2 (8 mmol) was added in one portion. The slurry was stirred at room temperature for 20 min. The catalyst was filtered off and washed with methanol (5 ml). Ethyl acetate (5 ml) was added and resulting solution was dried with anhydrous sodium sulfate and evaporated in vacuo to afford the crude product which was purified by column chromatography on silica gel (10% EtOAc in hexane) to afford the pure sulfoxide. |
| 86% |
With C26H56P(1+)*C32H12BF24(1-); dihydrogen peroxide; In water; at 25℃; for 5h; |
General procedure: Typical procedure for the oxidation of the sulfides in [P4;4;4;14][B{C6H3-3,5-(CF3)2}4]: To a stirred solution of the sulfide (2 mmol, 0:24 mL) in 6b (0:50 mL), an aqueous solution of hydrogen peroxide (30% in water) (0:51 mL, 5 mmol) was added in 2 to 3 portions at room temperature. The progress of the reaction was followed by TLC. The reaction mixture was extracted with n-hexane-diethyl ether 2:1 v/v (5 x 5 mL), and the extract was dried over anhydrous MgSO4. The crude product was obtained by rolling evaporation and purified by column chromatography separation (silica gel using n-hexane-ethyl acetate 90:10 v/v). The yield and selectivity of methyl phenyl sulfoxide in kinetic and recycle experiments was calculated from calibration curves (r2 > 0:999) recorded using 3-methylanisole and 1,4-diacetylbenzene as internal standard. The WCCWCA was extracted with CH2Cl2 and then treated with MnO2 to destroy the excess peroxide. The obtained liquid was dried over anhydrous MgSO4 and then dried for 4 h in vacuo at 50C to remove CH2Cl2. Fresh substrate and hydrogen peroxide were then added for a new reaction cycle. All products were characterized by melting point, 1H NMR, 13C NMR and IR spectroscopy (see the Supporting Information). |
| 85% |
With dihydrogen peroxide; In water; acetonitrile; at 20℃; for 6h; |
General procedure: A solution of sulfide (1 mmol) and catalyst (100 mg), in acetonitrile (9 mL), was added to H2O2 35% (w/v) (2 mmol). The mixturewas stirred at 20C for a time period (see Tables 1 and 2). The solvent was evaporated and then H2O (5 mL) was added. The substrate was extracted with toluene (2 × mL) and dried with anhydrous Na2SO4; filtration and evaporation afforded the corresponding sulfoxides. The solid crude sulfoxides were purified by recrystallization to afford the pure sulfoxides |
| 80% |
With tert.-butylnitrite; water; pyridinium hydrobromide perbromide; In acetonitrile; at 25℃; for 4h; |
General procedure: Dissolve PyHBr3 (0.3 mmol) in water (1 ml). Transfer the solution into a 100 mlround bottom flask with substrate (10 mmol), CH3CN (20 ml), and TBN(0.4 mmol). The reaction mixture was stirred at room temperature (25 C)and air condition. Progress of the reaction was monitored by TLC and GC. Uponcompletion, the mixtures were removed and dissolved with CH2Cl2. Wash themixtures with HCl (1 10 ml), saturated sodium bicarbonate ((2 10ml), andwater (10 ml). The organic layer was dried over anhydrous Na2SO4. The yieldwas calculated on the basis of 10 mmol of substrate. Products are determinedby GC, 1H NMR, and 13C NMR. |
| 79% |
With C28H12Br4N12OV(4+)*4CBr3(1-); dihydrogen peroxide; In water; acetonitrile; at 20℃; for 22h; |
General procedure: A mixture of methyl phenyl sulfide (0.124 g, 1 mmol), [VO(TPPABr)]CBr3 (10 mg), and H2O2 (30 % aqueous, 6 mmol, 0.204 g,0.183 mL) in CH3CN (3 mL) was stirred for 120 min at room temperature.At the end of reaction, the catalyst was filtered and thesolvent was evaporated to afford the crude sulfoxide product.Finally, the product was purified by column chromatography usingethyl acetate/hexane (1.5:8.5) as eluent to give methyl phenyl sulfoxide as a white solid in 93% yield. |
| 58% |
With pyridine; methanol; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper(II) sulfate; at 65℃; under 760.051 Torr; for 48h;Schlenk technique; Green chemistry; |
General procedure: TEMPO (3.1mg, 0.02mmol), Methanol (1mL), CuSO4 (4.0mg, 0.03mmol), pyridine (8.1muL, 0.1mmol), and sulfides (0.5mmol), were added into the Schlenk tube (100mL). The reaction mixture was stirred at 65 and under O2 conditions for the given time. After the completion of the reaction, the reaction mixture was cooled to the room temperature, ethyl acetate (10mL) was added. And some solid was precipitated. Then, the mixture was filtered, and the solid was washed with petroleum ether and dried which was used directly in recycle experiments. The filtrate was concentrated under reduced pressure. The crude product was purified by column chromatography (silica 300-400, petroleum ether/ethyl acetate mixture = 5/1 and 2/1) to afford the product. |
| 24% |
With 1,3-dihydroxy-1H-1lambda3-benzo[d][1,2]iodoxol-1-yl trifluoromethanesulfonate; In acetonitrile; at 20℃; for 0.166667h;Inert atmosphere; |
General procedure: Sulfide 3 (0.125 mmol) was added to a solution of 2 (62 mg, 0.15 mmol) in acetonitrile (1 mL). The reaction was stirred at room temperature for 10 min to 1 h (reaction completion was controlled by TLC). After completion of the reaction, 5% aqueous Na2S2O3 (5 mL) and saturated NaHCO3 (5 mL) were added, and the mixture was extracted with dichloromethane. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification using short chromatographic column (hexane-ethyl acetate = 3 : 1) afforded analytically pure sulfoxide 4. |
| 88%Chromat. |
With dihydrogen peroxide; zinc dibromide; In methanol; water; at 20℃; for 6h;Air atmosphere; |
General procedure: In a 25 mL reaction tube, ZnBr2 (10 mol %), pyridine-2,6-dicarboxylic acid (10 mol %) and a stirring bar were added, followed by the addition of sulfides (1 mmol) and MeOH (2 mL) with syringe. At the end H2O2 (4 mmol; 30% aq) was added in one pot to the solution. The resulting solution was kept at room temperature for 6 h. Then hexadecane (100 mg) and ethyl acetate (3 ml) were injected, a part of the solution was taken for GC and GC-MS analysis after properly mixed. All the products are commercially available. The GC yields were calculated based on the calibration with commercially available products, and GC-MS spectroscopies were also compared. |
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With Ru2(3-hydroxybenzoate)4Cl; dihydrogen peroxide; In 1,2-dichloro-benzene; acetonitrile; for 0.33h;Catalytic behavior; |
General procedure: To a solution of 1.25mmol of methyl phenyl sulfide in 25mL CH3CN, 1% catalyst A, B, or C was dissolved along with 1.0mmol 1,2 dichlorobenzene for internal standard. Initiating the reaction with 8.0equivalents of hydrogen peroxide was carried out by adding the hydrogen peroxide drop wise over about 30s. Samples were taken at the indicated times by removing 300muL of reaction mixture and quenching the hydrogen peroxide with about 5mg of MnO2. From this sample, 2muL of solution was injected into GC for analysis under the conditions described above. For catalyst D, the reactions were completed in the same fashion, except that water: acetone (3:2, v/v) was used as solvent. Reactions with other sulfides were carried out at the same concentrations as the MPS reactions above. However these reactions were scaled down to 10mL MeCN, 0.50mmol sulfide, 0.4mmol 1,2-dichlorobenzene, and 8equiv hydrogen peroxide. The reactions were sampled at the indicated times by quenching the unreacted hydrogen peroxide with MnO2 as above. Samples were analyzed via gas chromatography and percentages determined via standard curves for purchased sulfides and synthesized sulfoxides and sulfones. |
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With dihydrogen peroxide; In water; at 20℃; for 0.05h;Green chemistry; |
General procedure: A round-bottomed flask was charged with sulfide (1 mmol), H2O2 (30% aqueous, 0.5 mL) and Fe3O4-AMPD-Cu (0.005 g). The mixture was stirred at room temperature until reaction completion, as monitored by TLC. The catalyst was removed with a magnet, and the residue was extracted with ethyl acetate. The organic extract was dried over anhydrous Na2SO4 and then evaporated to give the desired product without further purification. |
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With oxone; In water; acetonitrile; at 20℃; |
General procedure: To a well-stirred solution of thioether (1 mmol) in aqueous-acetonitrile (3:1, 4 mL)was added dropwise a solution of Oxone (0.7 mmol) in water (6 mL). Stirring wascontinued and the reaction was monitored by TLC. Upon completion of the reaction,the mixture was diluted with chilled water. The resultant sulfoxide, if solid, wasfiltered, washed with water and dried, or otherwise the reaction mixture wasextracted with ethyl acetate. The organic extract was washed with water, dried overanhydrous sodium sulfate and the solvent was removed. The resultant residue wasfiltered through a short column of silica gel. Elution with petroleum ether-ethylacetate (98:2%, v/v) afforded the pure sulfoxide. |
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