Efficient one-pot construction of unsymmetrical disulfide bonds with TCCA

We report herein a one-pot synthesis of unsymmetrical disulfides with trichloroisocyanuric acid (TCCA) as an oxidant. Under facile conditions, aromatic-aromatic disulfides and aromatic-aliphatic disulfides were synthesized in good to excellent yields even without base. For the construction of the challenging aliphatic-aliphatic disulfides, good yields of the desired products were also obtained with slightly modified conditions. Additionally, the reactions demonstrated a wide range of substrate scope, very short reaction time (<5 min), and convenient procedures.     

一氟甲基二硫化物的高效合成

以PhSO2SCH2F为一氟甲硫基化试剂,室温下实现了硫酚/硫醇的一氟甲硫基化反应,高收率地合成了一系列一氟甲基二硫化物.该方法具有反应时间短、条件温和、操作简单以及无需外加添加剂等特点,为高效制备一氟甲基二硫化物提供了一条简便的途径.     

N-Trifluoroacetyl arenesulfenamides, effective precursors for synthesis of unsymmetrical disulfides and sulfenamides

N-Trifluoroacetyl arenesulfenamides (3) were effective precursors for the synthesis of unsymmetrical disulfides (4) and sulfenamides (5). Reactions of 3 with a variety of aromatic thiols at room temperature were generally complete within 5 min and gave unsymmetrical diaryl disulfides in high yields. Aralkyl disulfides were isolated in high yields from the reaction of 3 with aliphatic thiols. The nucleophilic substitution reactions of 3 with amines proceeded smoothly and provided N-substituted sulfenamides in good to excellent yields.     

二碘化钐促进的二硫代氨基甲酸酯和硫代氨基甲酸酯的还原断裂反应

室温下SmI2-THF-HMPA-t-BuOH体系可顺利地将二硫代氨基甲酸酯还原断裂得到二硫醚和硫代甲酰胺; 同样条件下, 硫代氨基甲酸酯还原断裂得到二硫醚篅34The reductive cleavage of dithiocarbamic esters are promoted by the SmI2-HMPA-THF-t-BuOH System successfully to give disulfides and thiocarboxamides at room temperature in good yields; The reduction of thiocarbamic esters are also promoted by the same system to give disulfides and carboxamides.     

Versatile Synthesis of Fused Tricyclic 1,2,4-Triazole Derivatives

ABSTRACT

A rapid and general method for the synthesis of symmetrical disulfides involves reaction of sulfur with sodium hydroxide under PTC-microwave irradiation condition to give sodium disulfide, which reacts with alkyl halides to afford the disulfides in good to excellent isolated yields.     

Sulfur Transfer Reactions of Tetrathiomolybdate in Water: Synthesis of Alkyl Disulfides from Alkyl Halides

Abstract: Reaction of a number of alkyl halides with tetrathiomolybdate in water as the solvent affords the corresponding disulfides in good yields.     

H14[NaP5W30O110] as a heterogeneous recyclable catalyst for the air oxidation of thiols under solvent free conditions

The catalytic oxidation of thiols to the corresponding disulfides using Preyssler's catalyst H(14)[NaP(5)W(30)O(110)] has been studied. These highly selective oxidations gave good yields of the target disulfides.     

Rapid and efficient synthesis of symmetrical alkyl disulfides under phase transfer conditions

A one-pot, rapid and general method for the synthesis of symmetrical disulfides based on reaction of sulfur with sodium sulfide in the presence of didecyldimethylammonium bromide (DDAB) as a phase transfer catalyst is reported. Reaction with a variety of alkyl halides, at room temperature, afforded the disulfides in good to excellent isolated yields in a short time.     

Glycerol as a recyclable solvent in a microwave-assisted synthesis of disulfides

Abstract

We present here a clean and fast synthesis of organic disulfides starting from thiols using glycerol as solvent under microwave irradiation. This efficient method is general for aromatic, aliphatic, and functionalized thiols, affording the corresponding disulfides in good to excellent yields after easy work up. Glycerol can be easily recovered and utilized for further oxidation reactions.     

Novel Reductive Cleavage Reaction of Thiobenzoates with Samarium Diiodide: Convenient Synthesis of Disulfides

The reductive cleavage of thiobenzoates promoted by samarium diiodide afforded various kinds of disulfides in good yields under mild and neutral conditions.     

Synthesis of Diaryl Disulfides via Mild Reduction of Arylsulfinates with Hydrazine Monohydrate in DMSO

Arylsulfinates were reduced with hydrazine monohydrate at room temperature in dimethylsulfoxide (DMSO) to afford diaryl disulfides in good yields. A dramatic solvent effect was observed, and DMSO was found to be the best solvent for the reaction.     

The palladium‐catalyzed C‐N cross‐coupling reaction of diheteroaryl disulfides with heterocyclic amines

The Pd‐catalyzed cross‐coupling reaction of 1, 2‐di(pyrimidin‐2‐yl) disulfides with heterocyclic amines including 2‐amino pyrimidines and 1,3,4‐thiadiazol‐2‐amines to deliver symmetrical C‐N coupling products in moderate to good yields is reported. This method provides an opportunity for synthesis of bioactive molecules and pharmaceutically interesting compounds containing heterocycle motifs. The reported protocol shows good functional group compatibility, and provides a new strategy for preparation of C2‐amination pyrimidine derivatives from heterocyclic disulfides.     

EFFICIENT AND SELECTIVE OXIDATION OF THIOLS TO DISULFIDES BY 1,4-DIAZABICYCLO[2.2.2]OCTANE-DI-N-OXIDE-DI-PERHYDRATE UNDER NEUTRAL AND HETEROGENEOUS CONDITIONS

1,4-Diazabicyclo[2.2.2]octane-di-N-oxide-di-perhydrate[3pc] selectively oxidizes thiols to disulfides in acetonitrile in good yields. The method is generally useful for a wide variety of thiols.     

Sulfenylation of nitroalkanes and hydroxyaryls

The sulfenylation of nitroalkanes and hydroxyaryls in DMSO using aryl disulfides as sulfenylating reagents was studied. The corresponding arylthionitroalkanes and arylthiohydroxyaryls were obtained in moderate to good yields in very mild conditions, thus improving the reported procedures for the synthesis of these compounds.     

Reductive Cleavage of S-S Bond by Samarium Diiodide: A Novel Method for the Synthesis of Disulfides

Samarium diiodide reductively cleaves the S-S bond of sodium alkyl thiosulfates to give the corresponding disulfides in moderate to good yields under mild and neutral conditions.     

Metal-Free and NBS-Mediated Direct Thiol-Disulfide Exchange Reaction to Access Unsymmetrical Disulfides

A metal-free and N-Bromosuccinimide (NBS)-mediated direct thiol-disulfide exchange reaction at room temperature is developed. A variety of unsymmetrical disulfides have been prepared with good to excellent yields. Efficient late-stage modification of amino acids and drugs demonstrates the utility of this strategy. In addition, easy to operate, broad substrate scope and good functional group tolerance further demonstrate that this reaction provides an essential complementary route to access unsymmetrical disulfides.     

锡促进的烯丙基硒醚和烯丙基硫醚的合成

在金属锡促进下，烯丙基溴与二硒醚或二硫醚反应，生成烯丙基硒醚或烯丙基硫醚 。     

Preparation of Disulfides by Reduction of Sodium Alkyl Thiosulfates with Metallic Samarium and Catalytic Amount of Iodine

Sm/I₂ reduces sodium alkyl thiosulfates to the corresponding disulfides in good to excellent yields in THF at room temperature.     

A new method for synthesis of S-aryl-O-alkyl thiolcarbonates: selenium-catalyzed reaction of alcohols with carbon monoxide and diaryl disulfides

A unique catalytic ability of selenium has been developed. When alcohols were allowed to react with diaryl disulfides in the presence of a catalytic amount of selenium under a pressurized carbon monoxide, S-aryl-O-alkyl thiolcarbonates were obtained in moderate to good yields.     

Stereoselective Michael Addition and Michael-aldol Tandem Reaction of Diorganyl Diselenides or Disulfides with Conjugated Alkynones Mediated by Samarium Diiodide

Stereoselective Michael addition and Michael-aldol tandem reaction of diorganyl diselenides and disulfides with conjugated alkynones mediated by samarium diiodide were studied. The reaction temperature was critical for the stereoselectivity, β-Organylselenoalkenones or β-organylthioalkenones and γ-organylselenoallylic alcohols or γ-organylthioallylic alcohols were prepared in good yields.