| 99% |
With 1-n-butyl-3-methylimidazolium methylselenite at 100℃; for 3h; |
General procedure for the oxidation of thiols with [bmim][SeO2(OCH3)]:
Method A: In a Schlenk tube under open atmosphere and at room temperature, the corresponding thiol (1.0 mmol) was added to [bmim][SeO2(OCH3)]10 (1.0 mL). The reaction mixture was allowed to stir at 60 °C for the time indicated in Table 1. The progress of the reaction was monitored by TLC. Method B: In a 10 mL glass vial equipped with a small magnetic stirring bar, containing 1.0 mL of [bmim][SeO2(OCH3)] was added the thiol (1.0 mmol). The vial was tightly sealed with an aluminum/Teflon crimp top. The mixture was then irradiated in a microwave reactor (CEM Explorer) for the time indicated in Table 2 at 30 °C (temperature was measured with an IR sensor on the outer surface of the reaction vial), using an irradiation power of 100 W and pressure of 150 psi. After the reaction was complete, the product was extracted by successive washings with petroleum ether (3 × 5 mL), dried over MgSO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate/hexanes as the eluent. |
| 99% |
With poly(4-vinylpyridinium nitrate) I In acetonitrile at 20℃; for 2.5h; |
|
| 99% |
With poly(4-vinylpyridinium tribromide) In dichloromethane at 20℃; for 0.666667h; |
|
| 99% |
With silica sulfuric acid; potassium iodide at 20℃; for 0.25h; |
General procedure for the oxidative coupling of thiols using PVPP-H2O2/SiO2-OSO3H/KI
General procedure: To a suspension of polyvinylpolypyrrolidone-supported hydrogen peroxide (0.175 g),silica sulfuric acid (0.1 g) and potassium iodide (0.02 mmol) in dichloromethane or ethylacetate (5 mL) was added a thiol (1 mmol), and the mixture was stirred at room temperaturefor the specified time (Table I). The progress of the reaction was monitored by TLC. Aftercompletion of the reaction, the reaction mixture was filtered and the residue washed withCH2Cl2 (20 mL), (the residue of entry 5 was washed with ethanol). Finally, the organicsolvent was evaporated and pure product was obtained as judged by TLC and 1H-NMRspectroscopy. |
| 99% |
With polyvinylpolypyrrolidonium tribromide In ethanol at 20℃; for 0.133333h; Green chemistry; |
General procedure: A 25 mL round-bottom flask was charged with thiol (1 mmol), polyvinylpolypyrrolidoniume tribromide (1.2 gr), and EtOH(5 mL) as solvent. The reaction mixture was stirred at room temperature, and the progressof the reaction was monitored by TLC. After completion of the reaction, corresponding disulfides easily obtained by passing of reaction mixture through a short column using dichlromethane and acetone (95:5) as eluent. |
| 99% |
With dihydrogen peroxide In lithium hydroxide monohydrate; acetonitrile at 20℃; for 0.25h; Green chemistry; chemoselective reaction; |
2.3. Typical procedure for selective oxidation of thiols to disulfides
General procedure: In a typical oxidative coupling reaction, 2 mmol thiophenol was dissolved in acetonitril (3 mL). Then 0.03 g (0.02 mmol) catalyst and 0.25 g hydrogenperoxide (30% aqueous) were added. The reaction mixture was stirred for the various reaction times as indicated in Table 2. After the completion of the reaction (determined by TLC), which is associated with precipitation of disulfide and elimination of thiol odor. The catalyst was separated by filtration, washed with ethyl acetate and heated at 60 °C prior to its reuse in the next reaction. The combined organic filtrates were then washed with water and the organic layer separated and dried over magnesium sulfate. The product was obtained after removal of the solvent. The conversion was determined by isolated yield and compounds were characterized by 1H and 13C NMR. In most cases, the products could be isolated in their pure forms by simple filtration and evaporation of the solvent. |
| 99% |
With salen complex of Cu(II) immobilized on Fe3O4 nanoparticles; dihydrogen peroxide In ethanol at 20℃; for 2h; |
2.6 General procedure for the oxidative coupling of thiols
General procedure: A 25mL round-bottom flask was charged with thiol (1mmol), H2O2 33% (0.5mL), and catalyst (0.01g) in ethanol as solvent. The reaction mixture was stirred at room temperature, and the progress of the reaction was monitored by TLC. After completion of the reaction, the catalyst was separated by an external magnet and the product was extracted with CH2Cl2. The combined organics were washed with water (5mL) and dried over anhydrous Na2SO4. Finally, the solvent was removed to give the corresponding pure disulfides |
| 99% |
With Eosin In ethanol for 16h; Irradiation; |
|
| 99% |
With dihydrogen peroxide In ethanol at 20℃; for 0.5h; Green chemistry; chemoselective reaction; |
2.5. General procedure for the oxidative coupling of thiols into disulfides using H2O2 in the presence of M-Salen-MNPs
General procedure: M-Salen-MNPs (0.01 g) was added to a mixture of thiol (1 mmol) and H2O2 (0.4 mL) in ethanol (5 mL). Then the mixture was stirred for the appropriate time at room temperature. The progress was monitored by TLC. After completion of the reaction, the catalyst was separated by an external magnet and the mixture was washed with ethyl acetate. The product was extracted with ethylacetate. The organic layer was dried over anhydrous Na2SO4 (1.5 g). In some cases, the product was recrystallized from ethanol for further purification and products were obtained in good to high yield. |
| 99% |
With dihydrogen peroxide In dichloromethane at 20℃; for 1.66667h; |
|
| 99% |
With (S)-tetrahydrotellurophen-3-amine hydrochloride; dihydrogen peroxide In dichloromethane at 25℃; Flow reactor; |
|
| 98% |
With calcium hypochlorite; Montmorillonite K10 In hexane at 20℃; for 0.5h; |
|
| 98% |
With aluminum(III) oxide; dimethyl sulfoxide at 40℃; for 0.5h; |
|
| 98% |
With tungstate sulfuric acid; NaNO2 In dichloromethane at 20℃; for 0.116667h; |
|
| 98% |
With trimethylphenylammonium perbromide In ethyl acetate at 20℃; for 0.0833333h; |
|
| 98% |
With aluminum(III) oxide In neat (no solvent) for 0.333333h; Milling; chemoselective reaction; |
|
| 98% |
With potassium bromate; hexaammonium heptamolybdate tetrahydrate In lithium hydroxide monohydrate; acetonitrile at 20℃; for 0.0833333h; |
Typical Procedure
General procedure: 4-chlorothiophenol (0.145 g, 1 mmol) was added to a heterogeneous mixture of KBrO3 (0.167 g, 1 mmol), (NH4)6Mo7O24·4H2O (0.124 g, 10 mmol%), and CH3CN/H2O (7:3) (5 mL) and the mixture was stirred under a hood for 4 min at ambient atmosphere and room temperature. The progress of the reaction was monitored by TLC (eluent: EtOAc/n-C6H14, 1/13). After completion, CH2Cl2 (20 mL) was added and the reaction mixture was filtered. The filtrate was washed with 5% NaOH, water, and dried over anhydrous MgSO4. Finally, evaporation of the solvent gave the product with sufficient purity formost purposes |
| 98% |
With Cu(NO<SUB>3</SUB>)<SUB>2</SUB>3H<SUB>2</SUB>O In lithium hydroxide monohydrate; ethyl acetate at 20℃; for 0.3h; Green chemistry; |
|
| 98% |
With dihydrogen peroxide In ethanol at 20℃; for 2h; |
|
| 98% |
With dihydrogen peroxide In ethanol at 20℃; for 2h; |
|
| 98% |
With titanium(IV) dioxide; oxygen In acetonitrile for 0.0833333h; Irradiation; |
|
| 97% |
With oxygen In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 4h; |
|
| 97% |
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.25h; chemoselective reaction; |
|
| 97% |
With dihydrogen peroxide In ethanol at 20℃; for 3h; Green chemistry; |
General procedure for oxidative coupling of thiols
General procedure: Dopamine sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (DSA(at)MNPs) (0.004 g) were added to solution of thiol (1 mmol) and H2O2 33 % (0.5 mL) in ethanol (10 mL). The reaction mixture was stirred at room temperature, and the progress of the reaction was monitored by TLC. After completion of the reaction, the catalyst was separated using an external magnet, and the product was extracted with CH2Cl2 and dried over anhydrous Na2SO4. Finally, the solvent was removed by simple evaporation to give the corresponding pure disulfides. |
| 97% |
With dihydrogen peroxide In ethanol at 20℃; for 0.333333h; Green chemistry; |
General procedure for the oxidative coupling of thiols to the disulfides
General procedure: A mixture of thiol (1 mmol), hydrogen peroxide (0.5 mL) and the catalyst (0.005 g) in ethanol (2 mL) was stirred at ambient temperature. Reaction progress 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 disulfides were obtained in high to excellent yields (88-98%). |
| 97% |
With dihydrogen peroxide In acetonitrile at 20℃; for 0.583333h; Green chemistry; |
|
| 97% |
With iron phthalocyanine In tetrahydrofuran at 20℃; for 0.333333h; |
|
| 97% |
With dihydrogen peroxide In ethanol; lithium hydroxide monohydrate at 20℃; for 0.333333h; Green chemistry; |
General procedure for the oxidative coupling of thiols into disulfides
General procedure: Fe3O4MCM-41Ni-P2C (10 mg) was added to a mixture of thiol (1 mmol) and 33% H2O2 (0.4 mL) in ethanol (3 mL). The resulting reaction mixture was stirred for the specified time at room temperature (the progress of reaction was monitored by TLC). After completion of the reaction, the catalyst was separated by an external magnet and the product was washed with ethyl acetate. Then organic layer was dried over anhydrous Na2SO4 (1.5 g). Finally, the organic solvent was removed by simple evaporation and disulfides were obtained in very high isolated yields. |
| 97% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol for 1.75h; Sealed tube; Irradiation; chemoselective reaction; |
3.2 Procedure for the oxidation of thiols to disulfides
General procedure: 0.6 mmol of thiol 1 and 90 μL (1/3 mol/L) TEMPO/EtOH (and 1.8 mmol of thiol 3) were combined in a 10 mL Pyrex vessel with 1 mL of EtOH dissolved. Subsequently, O2 was injected into the sealed vessel to reach 0.1 MPa of pressure. Then the reaction mixture was magnetically stirred at 1500 rpm and simultaneously illuminated with 3 W blue LEDs until it came to an end monitored by thin layer chromatography (TLC). The reaction pressure was released and the crude products were purified with column chromatograph (petroleum ether: ethyl acetate = 80:1). Then the target product was obtained. |
| 96% |
With dimethyl sulfoxide at 90℃; for 6h; |
|
| 96% |
With potassium permanganate supported on montmorillonite K10 In dichloromethane at 20℃; for 0.5h; |
|
| 96% |
With nickel(II) ferrite; dihydrogen peroxide In acetonitrile at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction; |
|
| 96% |
With dihydrogen peroxide In ethanol at 20℃; for 2h; Green chemistry; |
|
| 96% |
With dihydrogen peroxide In ethyl acetate at 20℃; for 2.66667h; |
General procedure for the oxidative coupling of thiols
General procedure: Boehmite-SSA (0.002 g) was added to a mixture of thiol(1 mmol) and H2O2 (0.4 mL) in ethyl acetate (2 mL). Then,the mixture was stirred for the appropriate time at room temperature. The progress of reaction was monitored byTLC. After completion of the reaction, the catalyst was separated by filtration and the mixture was washed with ethyl acetate. The product was extracted with ethyl acetate.The organic layer was dried over anhydrous Na2SO4(1.5 g). The products were obtained in good to high yield. |
| 96% |
With dihydrogen peroxide In ethanol at 20℃; for 0.5h; Green chemistry; |
|
| 96% |
With dihydrogen peroxide In ethanol at 20℃; for 0.416667h; |
General procedure for the oxidative coupling of thiols to thedisulfdes:
General procedure: A mixture of thiol (1 mmol), hydrogen peroxide (0.5 mL)and Fe3O4 MNPs-DETA/Benzyl-Br3 (12.5 × 10-3 mol%) inethanol (2 mL) was stirred at ambient temperature. Reactionprogress was monitored by TLC (acetone: n-hexane, 2:8). Aftercompletion of the reaction, catalyst was separated by externalmagnet and washed with ethyl acetate, and next, the productwas extracted with ethyl acetate (4 × 5 mL). The organic layerwas dried over anhydrous Na2SO4 (1.5 g). Finally, the organic solvents were evaporated, and the corresponding disulfdeswere obtained in high to excellent yields (89-98%).All the products are known compounds and were characterized by comparison of their IR and NMR spectraldata and physical properties with those reported in theliterature. |
| 95% |
With aluminum(III) oxide; sodium periodate In hexane at 20℃; for 0.5h; |
|
| 95% |
With 1,4-diazabicyclo[2.2.2]octane N,N′-dioxide In acetonitrile for 1h; Heating; |
|
| 95% |
With maleic anhydride; urea-hydrogen peroxide In methanol at 0℃; for 0.166667h; |
|
| 95% |
With 1H-imidazole; [N,N'-bis(salicylidene)-o-phenylenediaminato]manganese(III) chloride; urea hydrogen peroxide In methanol at 0℃; for 0.166667h; |
|
| 95% |
With rosolic acid In methanol at 20℃; for 1h; |
|
| 95% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0℃; for 0.0833333h; |
4.2. General procedure for the synthesis of disulfides
Procedure for symmetrical molecules: DDQ (0.5 mmol) was added to an ice-cooled solution of thiol (1 mmol) in dichloromethane (3.0 mL). The reaction mixture stirred for 5 min at 0 °C and monitored by TLC analysis. The reaction mixture was concentrated under reduced pressure and directly purified by column chromatography by gradient elution of ethyl acetate in hexanes to give the title compounds. |
| 95% |
With dihydrogen peroxide; trichlorophosphate In diethyl ether; lithium hydroxide monohydrate at 0℃; for 0.0833333h; |
|
| 95% |
With dihydrogen peroxide In ethanol; lithium hydroxide monohydrate at 20℃; for 2h; |
|
| 95% |
With silica gel-supported iodine monochloride In chloroform at 20℃; for 0.666667h; |
|
| 95% |
With dihydrogen peroxide; N,N,N-tributyl-1-butanaminium iodide In lithium hydroxide monohydrate at 20℃; for 1.08333h; Large scale reaction; |
|
| 95% |
With urea hydrogen peroxide addition compound In ethanol at 20℃; for 0.433333h; |
Typical procedure for the synthesis of disulfides catalyzed by Co(at)MCM-41 or Fe(at)MCM-41: as a typical procedure
General procedure: A mixture of thiols (1 mmol), UHP (5 mmol), and Co orFeMCM-41 (20 mg) was stirred at room temperature inethanol and the progress of the reaction was monitored by TLC.After completion of the reaction, the catalyst was removed andthe products were extracted with CH2Cl2 (3 × 10 mL). Theresults are shown in Table 7. |
| 95% |
With magnetic ion exchanged Montmorillonite-k10 In tetrahydrofuran at 50℃; for 1h; Green chemistry; |
|
| 95% |
With iodine In ethanol at 20℃; for 18h; |
|
| 95% |
With dihydrogen peroxide In neat (no solvent) at 20℃; for 1.33333h; Green chemistry; |
|
| 95% |
With dihydrogen peroxide In ethanol; lithium hydroxide monohydrate at 20℃; for 0.333333h; |
General procedure for the oxidative coupling of thiols into disulfides
General procedure: A mixture of thiol (1 mmol), 33 % H2O2 (0.4 mL) and Fe3O4MCM-41VO-SPATB (10 mg) in ethanol (3 mL) was stirred for the specified time at ambient temperature (the progress of reaction was monitored by TLC). After completion of the reaction, the catalyst was separated by applying an external magnet and the product was washed with ethyl acetate, and then dried over anhydrous Na2SO4 (1.5 g). Finally, Evaporation of the solvent gave the disulfides invery high isolated yields |
| 95% |
With dihydrogen peroxide In ethanol at 20℃; for 1.33333h; Green chemistry; |
|
| 94% |
With butyltriphenylphosphonium dichromate In acetonitrile for 0.025h; Microwave irradiation; |
|
| 94% |
With γ-picolinium chlorochromate In dichloromethane at 20℃; for 0.6h; |
|
| 94% |
With graphite oxide In chloroform at 100℃; for 0.166667h; |
|
| 94% |
With air In ethanol at 20℃; for 4h; |
Thiol coupling reactions for the synthesis of disulfides
General procedure: General procedure (1mM scale): In a 25 mL round bottom flask, a thiol(1; 1.0 mmol) was dissolved in EtOH (1 mL) and the mixture was stirredin the open atmosphere for 4 h (completion of reaction was confirmedby TLC). Then the mixture in the flask was evaporated in vacuo. Theresidue was either directly dried to give pure products 2a-i or subjectedto silica gel column chromatography using petroleum ether as eluent togive pure products 2j-l (see Table 2).General procedure (10 mM scale): In a 50 mL round bottom flask,a thiol (1a, 1b or 1d; 10.0 mmol) was dissolved in EtOH (10 mL) andthe mixture was stirred in the open atmosphere for 6 h (progress ofreaction was followed by TLC). Evaporation of solvent provided thecorresponding pure disulfides 2a, 2b and 2d. |
| 94% |
With dihydrogen peroxide In ethanol at 20℃; for 0.75h; Green chemistry; |
|
| 94% |
With dihydrogen peroxide In ethanol at 20℃; for 0.833333h; |
General procedure for the oxidative coupling of thiols
General procedure: To the mixture of the thiol (1 mmol) and Fe3O4*MCM-41Zn-Arg (15 mg) in ethanol (3 mL), H2O2 (0.4 mL) was added and stirred at room temperature. After completion ofthe reaction (monitored by TLC), the catalyst was separated from the mixture by an external magnet and the product was extracted with ethyl acetate and the solvent was removed by simple evaporation to give pure disulfides. |
| 93% |
With sodium (meta)periodate In lithium hydroxide monohydrate at 20℃; for 0.0333333h; |
|
| 93% |
With nicotinic acid hydrobromide perbromide at 20℃; for 0.0833333h; Neat (no solvent); |
|
| 93% |
With [Mn(III)(BHBPDI)Cl]; oxygen In ethanol at 20℃; for 1h; |
|
| 93% |
With hydrogen bromide; dimethyl sulfoxide In chloroform at 20℃; for 6h; Inert atmosphere; Schlenk technique; |
General procedure for the synthesis of symmetrical disulfides:
General procedure: A mixture of thiols(1.0 mmol) and HX (0.2 mmol) in DMSO-CHCl3 (5 mL, 1:1, v/v) was stirred atroom temperature for respective time (Table 3). After the completion of thereaction, as monitored by TLC, the reaction mixture was diluted with 10 mL ofwater and extracted with CHCl3 (3 15 mL). The combined organic layerswere washed with brine (2 10 mL), dried over anhydrous Na2SO4, andevaporated in a rotary evaporator under reduced pressure. A reasonably pureproduct obtained was further purified by recrystallization using hexane-CHCl3mixture. The purity of the compound was confirmed by melting point andNMR measurements. |
| 93% |
With potassium carbonate; copper chloride (II) In methanol |
|
| 93% |
With H5PV2Mo10O40; oxygen In ethanol; lithium hydroxide monohydrate at 90℃; for 5.5h; Green chemistry; |
|
| 92% |
With calcium hypochlorite; lithium hydroxide monohydrate; mesoporous silica In hexane at 20℃; for 0.333333h; |
|
| 92% |
With air In hexane at 30℃; for 2h; |
|
| 92% |
With ethylenebis(N-methylimidazolium) chlorochromate In acetonitrile at 20℃; for 0.0833333h; |
|
| 92% |
With 1,3-dibromo-5,5-dimethylhydantoin In chloroform at 20℃; for 1h; Inert atmosphere; |
|
| 92% |
With tert.-butylnitrite; oxygen In 1,2-dichloro-ethane at 50℃; for 2h; Sealed tube; Green chemistry; |
Typical procedure for disulfides (2a)
General procedure: A sealed tube (90 mL) equipped with a magnetic stirring bar and an O2 balloon was charged with dichloroethane (DCE, 20 mL), thiophenol (1a, 4 mmol, 0.44 g) and TBN (0.16 mmol, 4 mol%, 19.2 mL). Then the tube was placed in an oil bath, which was preheated to 50°C. The mixture was stirred for 1 h until starting material was completely consumed as monitored by GC and TLC. After removing the solvent, the residue was purified by column chromatography on silica gel to give the desired diphenyl disulfide (2a, 90%, 0.394 g) as a white solid. |
| 92% |
With urea hydrogen peroxide addition compound In ethanol at 20℃; for 0.3h; |
General procedure for oxidative coupling of thiols to disulfides with UHP catalyzed by Cr-MCM-41 and Mn-MCM-41
General procedure: Thiols ((1 mmol), 5 mmol UHP, and 4 mL acetone as solvent along with 25 mg catalyst were added to a 10-mL two-necked flask equipped with a stirrer. The progress of the reaction was monitored by TLC. After completion of the reaction, the catalyst was removed and the pure products were extracted with CH2Cl2(3 9 10 mL). The results are presented in Table 6. |
| 91% |
With urea hydrogen peroxide addition compound In acetonitrile at 20℃; for 0.333333h; |
|
| 91% |
With dihydrogen peroxide In ethanol at 20℃; for 0.916667h; Green chemistry; chemoselective reaction; |
|
| 91% |
With trimethylphenylammonium perbromide In tetrahydrofuran at 30℃; for 4h; |
General experimental procedure (C) for the synthesis of disulfane:
General procedure: To a well stirred solution of Thiols (1equiv.) in THF Phenyl Trimethyl ammonium Tribromide (PTAB) (0.5 equiv) was added and the reaction was stirred at room tempearature for 4-8 hrs. After completion of the reaction which was monitored by TLC, The reaction mixture was quenched with distilled water and extracted with ethyl acetate (3X3ml). The organic fraction was washed with saturated brine solution and dried over oven dried anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. The residual crude mass was subjected to a short silica gel column filtration (petroleum ether/ethyl acetate) afforded the desired disulfane as the pure product. |
| 91% |
With dihydrogen peroxide In ethanol at 20℃; for 0.25h; |
2.5 General Procedure for the Oxidation of Thiolsto Disulfides
General procedure: General experimental procedure for the oxidative couplingof thiols is as following: MCM-41(at)Tryptophan-M (Cd orHg) (0.005) was added to a mixture of thiol (1 mmol) andH2O2(0.5 mL) in ethanol (3 mL). Then the mixture wasmagnetically stirred for the appropriate time at room temperature.The progress of reaction was monitored by TLC.After completion of the reaction, the catalyst was removedby filtration and the mixture was washed with ethyl acetate.The product was extracted with ethyl acetate. After the evaporationof ethyl acetate, the pure product was obtained bycrystallization from ethanol (Scheme 3). |
| 90% |
With p-nitro-α-oxo-benzeneacetaldehyde; glacial acetic acid for 0.333333h; Reflux; |
|
| 90% |
With guanidinium nitrate In dichloromethane at 20℃; for 0.283333h; chemoselective reaction; |
|
| 90% |
With dihydrogen peroxide In lithium hydroxide monohydrate; ethyl acetate at 20℃; for 0.5h; Green chemistry; |
General procedure for the oxidation of thiols to disulfides
General procedure: In another study, a mixture of the VO-AMPD(at)SBA-15 (0.004 g), thiol (1 mmol) and H2O2 (0.4 mL) was stirred at room temperature in ethyl acetate (2 mL). The progress was monitored by TLC. After completion of the reaction, VO-AMPD(at)SBA-15 catalyst was separated from the mixture by filtration. Then products were extracted with ethyl acetate and dried, and the solvent was removed to give the pure disulfides. |
| 90% |
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.5h; Green chemistry; chemoselective reaction; |
|
| 90% |
With urea hydrogen peroxide addition compound In ethanol at 20℃; for 0.75h; |
|
| 89% |
With 10 wtpercent cubic Ag2O nanoparticle incorporated mesoporous silica; air In lithium hydroxide monohydrate for 5h; Reflux; Green chemistry; chemoselective reaction; |
|
| 89% |
With TiO2/MoS2 (10:1 molar ratio of Ti to Mo) nanocomposite; air In ethanol at 20℃; Irradiation; Green chemistry; |
General procedure for the synthesis of disulfides
General procedure: TiO2/MoS2 (10:1 molar ratio, 10 mg) was added to a solution of thiol 1 (1 mmol) in ethanol (1 mL). The reaction mixture was stirred under a 14W CFL irradiation at a distance of 10 cm at room temperature for a certain time. After reaction (monitored by thin-layer chromatography, TLC), ethyl acetate was added, and the solid catalyst was recovered by centrifugation. The reaction mixture was extracted with ethyl acetate and washed with water. The combined organic phase was then dried over Na2SO4 and concentrated under reduced pressure to give the crude residue, which was purified by column chromatography with petroleum ether-ethyl acetate to afford the pure product 2. The recovered catalyst was then washed with ethanol and deionized water, dried under vacuum, and reused for the next run. |
| 89% |
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.916667h; Green chemistry; |
|
| 89% |
With dihydrogen peroxide In neat (no solvent) at 20℃; for 0.916667h; |
2.4. General procedure for the oxidative coupling of thiols to thedisulfides
General procedure: 0.005 g Fe3O4-AMPD-Pd was added to a mixture including1 mmol thiol, 0.4 mL H2O2 33% and free solvent were stirred atroom temperature. The reaction was followed by TLC after completion.The nanocatalyst was isolated by a simple magnet. |
| 89% |
With titanosilicate molecular sieve In cyclohexane at 120℃; for 5h; Inert atmosphere; |
5
Weigh 30 mg of ETS-10 catalyst into a reaction tube, then add 0.22 mmol of p-bromothiophenol and 1 mL of cyclohexane.In a nitrogen atmosphere, the reaction was carried out in a heater at 120 °C for 5 h, and after the experiment was completed, centrifugation was performed.The solid phase product obtained was separated by flash column chromatography (the elution reagent was pure cyclohexane) to obtain a white solid.The product yield can reach 89% |
| 88% |
With urea hydrogen peroxide addition compound In methanol; dichloromethane at 20℃; for 2h; |
General conditions for catalytic oxidation of thiols
General procedure: A typical reaction using the Fe3O4(at)SiO2-NH2Mn(III) nanoparticles as catalyst and thiols as substrate is described as follows. To a solution of thiol (1 mM) and catalyst (0.01 g,containing 0.0002 mM of manganese complex) in a (1 : 1) mixture of CH3OH-CH2Cl2 (2 mL) was added UHP (0.093 g, 1 mM) as the oxidant. The mixture was stirred at room temperature for 2 h. The catalyst particles were then collected at the bottom of the test tube using a magnet, the supernatant was carefully decanted, and the completion of oxidation reaction was followed by TLC (petroleum ether/ethyl acetate, 4 : 1). After the separation of catalyst nanoparticles, the solvent supernatant was removed under vacuum and the remaining was purified by column chromatography using petroleum ether/ethyl acetate, 4 : 1. Isolated products were weighted and also analyzed by 1H NMR. Washing several timeswith methanol and dichloromethane, the catalyst particles were dried in vacuum and could be reused. |
| 88% |
With dihydrogen peroxide In ethanol at 20℃; for 1.5h; |
|
| 87% |
With dihydrogen peroxide In lithium hydroxide monohydrate at 20℃; for 0.416667h; Green chemistry; |
The typical procedure for oxidative couplingof thiols to disulfides with H2O2
General procedure: 1 mmol thiol, 20 mg of γ-Fe2O3 /CuHPECGs, and H2O2(0.4 mL, 3.92 mmol) were stirred at room temperaturein 2 mL of H2Ofor the specified time shown in Table 1.The reaction progress was monitored by TLC (n-hexane/ethyl acetate: 1:4). After completion of the reaction, the heterogeneous catalyst was magnetically separated from themixture and the product was extracted using ethyl acetate.The obtained products dried over anhydrous Na2SO4andorganic solvent evaporation were afforded pure product. |
| 86% |
With oxygen at 60℃; for 12h; Green chemistry; |
|
| 86% |
With 2,2'-(((diselanediylbis(2,1-phenylene))bis(azanediyl))bis(methylene))diphenol In acetonitrile at 20℃; for 7h; |
|
| 86% |
With oxygen; 1-n-hexyl-3-methylimidazol-1-ium bromide at 50℃; for 1.33333h; Green chemistry; |
|
| 86% |
With dihydrogen peroxide In ethanol at 25℃; for 1h; |
|
| 85% |
With sodium hydrogen sulphite; orthoperiodic acid In lithium hydroxide monohydrate at 20℃; for 1h; |
|
| 85% |
With ferric(III) chloride; sodium iodide In acetonitrile for 4h; |
|
| 85% |
With Bromotrichloromethane In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Irradiation; |
9 Example 9
Add 75.6mg (0.4mmol) of p-bromothiophenol and 237.9mg (1.2mmol) of bromotrichloromethane into a 10mL Schlenk container, and then add 2mL of tetrahydrofuran with a syringe, and react for 12h under the irradiation of a 23W energy-saving lamp at room temperature. After the reaction is complete After concentrating to remove the solvent, the crude product was separated by silica gel column chromatography (eluent: petroleum ether) to obtain a colorless liquid: 63.8 mg, yield: 85%. |
| 84% |
With bis(trichloromethyl) carbonate; triethylamine; Triphenylphosphine oxide In chloroform for 8h; Heating; |
|
| 84% |
With tris(2-phenylpyridinato-C<SUP>2</SUP>,N)iridium(III) In propan-2-one at 20℃; for 5h; Inert atmosphere; Sealed tube; Irradiation; Green chemistry; |
|
| 84% |
With Porcine Pancreas Lipase In lithium hydroxide monohydrate at 20℃; for 30h; Green chemistry; Enzymatic reaction; |
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