18523-73-4

Upstream product

• 33046-45-6 1-phenyl-2-(p-tolylthio)ethanone 
• 4541-89-3 2-chloro-1,1-diphenylethene 
• 10486-08-5 sodium p-thiocresolate 
• 33453-95-1 lithium p-toluenethiolate 
• 209391-60-6 [2-chloro-2-(p-tolylsulfinyl)ethene-1,1-diyl]dibenzene 
• 530-48-3 1,1-Diphenylethylene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 536-57-2 p-toluene sulfinic acid 
• 64-17-5 ethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 100954-03-8 phenyl 3-phenylprop-2-ynoate 
• 106-45-6 para-thiocresol 
• 98-86-2 acetophenone 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 70312-74-2 1-(2,2-diphenyl-ethenesulfonyl)-4-methyl-benzene 
• 43013-82-7 (2-(`methylsulfonyl)ethene-1,1-diyl)dibenzene 
• 141362-05-2 (2,2-diphenyl-vinyl)-p-tolyl sulfoxide 

Relevant academic research and scientific papers

Reaction of magnesium alkylidene carbenoids with lithium acetylides and lithium thiolates: A novel synthesis of conjugated enynes and vinyl sulfides

Magnesium alkylidene carbenoids were generated from 1-chlorovinyl p-tolyl sulfoxides with i-PrMgCl at -78°C in THF or toluene via the sulfoxide-magnesium exchange reaction. Reaction of the generated magnesium alkylidene carbenoids with lithium acetylides or lithium thiolates gave conjugated enynes or vinyl sulfides, respectively, in moderate to good yields. The intermediate of this reaction was found to be the alkenyl anion and it could be trapped with some electrophiles to give tetra-substituted conjugated enynes and vinyl sulfides.

Sodium iodide-mediated synthesis of vinyl sulfides and vinyl sulfones with solvent-controlled chemical selectivity

Vinyl sulfides and vinyl sulfones are ubiquitous structures in organic chemistry because of their presence in natural and biologically active compounds and are very frequently encountered structural motifs in organic synthesis. Herein we report an efficie

Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates

Herein, we have reported a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis. This protocol uses sulfinates as the sulfur source, and various thioethers could be synthesized under mild conditions. By mechanism exploration, we find that a cascade chemical step is allowed on the electrode interface and could alter the reaction pathway in paired electrolysis, whose findings could help the discovery of novel cascade reactions with unique reactivity.

Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source

We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.

Preparation method of thioether derivative

The invention discloses a preparation method of a thioether derivative, which comprises the following steps: (1) in a nitrogen atmosphere, mixing a sulfoxide compound, an olefin compound/alkyne compound/1, 3-dicarbonyl compound, an organic solvent and trifluoroacetic anhydride/trifluoromethanesulfonic anhydride, and reacting at 0-60 DEG C for 1-24 hours; (2) adding alkali into the material obtained in the step (1), reacting at room temperature for 0.5-1.5 hours, and washing with water to obtain an organic phase; and (3) carrying out post-treatment and purification on the organic phase obtained in the step (2) to obtain the thioether derivative. The method is suitable for constructing alkenyl thioether, alkynyl thioether and alkyl thioether derivatives at the same time, and is high in universality. The method has the advantages of easily available raw materials, high yield, mild reaction conditions, short reaction time, wide substrate range, strong reaction specificity, and simple and green post-treatment.

Direct Allylic C(sp3)?H and Vinylic C(sp2)?H Thiolation with Hydrogen Evolution by Quantum Dots and Visible Light

Direct allylic C?H thiolation is straightforward for allylic C(sp3)?S bond formation. However, strong interactions between thiol and transition metal catalysts lead to deactivation of the catalytic cycle or oxidation of sulfur atom under oxidative condition. Thus, direct allylic C(sp3)?H thiolation has proved difficult. Represented herein is an exceptional for direct, efficient, atom- and step-economic thiolation of allylic C(sp3)?H and thiol S?H under visible light irradiation. Radical trapping experiments and electron paramagnetic resonance (EPR) spectroscopy identified the allylic radical and thiyl radical generated on the surface of photocatalyst quantum dots (QDs). The C?S bond formation does not require external oxidants and radical initiators, and hydrogen (H2) is produced as byproduct. When vinylic C(sp2)?H was used instead of allylic C(sp3)?H bond, the radical-radical cross-coupling of C(sp2)?H and S?H was achieved with liberation of H2. Such a unique transformation opens up a door toward direct C?H and S?H coupling for valuable organosulfur chemistry.

Direct C-H Thiolation for Selective Cross-Coupling of Arenes with Thiophenols via Aerobic Visible-Light Catalysis

An aerobic metal-free, visible-light-induced regioselective thiolation of phenols with thiophenols is reported. The cross-coupling protocol exhibits great functional group tolerance and high regioselectivity. Mechanistic studies reveal that the disulfide

Electrochemical oxidative radical cascade cyclization of olefinic amides and thiophenols towards the synthesis of sulfurated benzoxazines, oxazolines and iminoisobenzofurans

Heterocycles containing N and O are important structures in pharmaceuticals, agrochemicals and functional molecules. The synthesis of these compounds usually requires complex substrates and harsh reaction conditions. Herein, we introduce a mild and efficient electrochemical oxidative strategy to construct benzoxazines, oxazolines and iminoisobenzofurans without the requirement of a transition-metal catalyst and an external oxidant. In a simple undivided cell, various olefinic amides and thiophenols/diselenides react to generate 69 examples of thiolation and selenylation heterocycles in up to 83% yields. Furthermore, this radical cascade reaction provided a facile method for constructing C-S/C-Se and C-O bonds in one step.

Thiol Activation toward Selective Thiolation of Aromatic C-H Bond

Direct C-S bond coupling is an attractive way to construct aryl sulfur ether, a building block for a variety of biological active molecules. Herein, we disclose an effective model for regioselective thiolation of the aromatic C-H bond by thiol activation instead of arene activation. Strikingly, this method has been applied into anisole derivatives that are not available in the arene activation approach to forge a single thioether isomer with high reactivity.

1,1-Diphenylvinylsulfide as a Functional AIEgen Derived from the Aggregation-Caused-Quenching Molecule 1,1-Diphenylethene through Simple Thioetherification

An efficient and readily scalable thioetherification between 1,1-diphenylethene (DPE) and sodium arylsulfinate was developed for the synthesis of 1,1-diphenylvinylsulfide (DPVS) with the yield up to 99 %. The photophysical properties of DPVS show that the introduction of arylsulfenyl groups onto the parent molecule DPE makes DPVS a novel type of aggregation-induced emission (AIE) luminogen (AIEgen) with large Stoke's shift (up to 188 nm). These DPVS possess AIE properties due to restriction of intramolecular motions (RIM), as demonstrated by crystal structure analysis. Importantly, the AIE performance of DPVS can be applied to sense the nitroaromatic explosive picric acid in aqueous systems through a “turn-off” response.