41424-40-2

Upstream product

• 536-74-3 phenylacetylene 
• 882-33-7 diphenyldisulfane 
• 35460-31-2 (2-phenylsulfanylethynyl)benzene 
• 108-98-5 thiophenol 
• 6293-66-9 diphenyliodonium p-toluenesulfonate 
• 66003-76-7 Diphenyliodonium triflate 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 59-88-1 phenylhydrazine hydrochloride 
• 931-59-9 benzenesulfenyl chloride 
• 128787-47-3 (E)-N-(4-nitrophenyl)-S-phenyl-S-<2-(phenylthio)-1-phenylvinyl>sulphimide 
• 133957-59-2 2-(trimethylsilyl)ethyl benzenesulfenate 
• 41424-41-3 (E)-(1-phenylethene-1,2-diyl)bis(phenylsulfane) 

Downstream Products

• 1148025-82-4 (E)-1-(4-dimethylaminoethoxyphenyl)-1,2-diphenyl-2-(4-tolyl)thioethene 
• 10540-29-1 tamoxifen 
• 41796-41-2 (Z)-1-(phenylthio)-2-methylstyrene 
• 6052-46-6 (Z)-(1,2-diphenylvinyl)(phenyl)sulfane 
• 875894-68-1 (Z)-1-(4-(methylphenyl)thio)-2-phenylstyrene 
• 16336-46-2 1-phenylthio-1-phenyl-1-propene 

Relevant academic research and scientific papers

Palladium-catalyzed bisthiolation of terminal alkynes for the assembly of diverse (Z)-1,2-bis(arylthio)alkene derivatives

An efficient and straightforward palladium-catalyzed three-component cascade bisthiolation of terminal alkynes and arylhydrazines with sodium thiosulfate (Na2S2O3) as the sulfur source for the assembly of functionalized (Z)-1,2-bis(arylthio)alkene derivatives is described. Using 0.5 mol% IPr-Pd-Im-Cl2as the catalyst, a wide range of terminal alkynes and arylhydrazines are well tolerated, thus producing the desired products in good yields with good functional group tolerance and excellent regioselectivity. Moreover, this protocol could be readily scaled up, showing potential applications in organic synthesis and material science.

Unconventional Reactivity of Ethynylbenziodoxolone Reagents and Thiols: Scope and Mechanism

1,2-Dithio-1-alkenes are biologically active compounds widely implemented throughout organic synthesis, functional materials, coordination chemistry, and pharmaceuticals. Traditional methods for accessing 1,2-dithio-1-alkenes often demand transition metal

Palladium-Catalyzed Regioselective Three-Component Cascade Bisthiolation of Terminal Alkynes

An efficient and novel NHC(N-heterocyclic carbene)-palladium-catalyzed three-component cascade bisthiolation of terminal alkynes, K2S (potassium sulfide) and diaryliodonium salts for the assembly of functionalized (Z)-1,2-bis(arylthio)alkene derivatives has been accomplished for the first time. This unique observation features a broad substrate scope, excellent functional-group tolerance, and high regioselectivity. Especially, an arylthiolate anion from diaryliodonium salts and potassium sulfide was proposed as the key intermediate in the catalytic cycle. (Figure presented.).

Nickel-Catalyzed Regioselective Cleavage of Csp2-S Bonds: Method for the Synthesis of Tri- and Tetrasubstituted Alkenes

We describe here an efficient route for the synthesis of (Z)-vinylic sulfides 3 via the highly regio- and stereoselective coupling of (Z)-1,2-bis(aryl(alkyl)thio)alkenes and Grignard reagents over a Ni catalyst under mild conditions. (Z)-Vinylic sulfides 3 are important intermediates in the synthesis of tri- and tetrasubstituted alkenes that are important construction blocks for drugs and natural products. The directing organosulfur groups (SR) can be converted to diaryl(alkyl) disulfides (RSSR) using H2O2 as oxidant, hence avoiding the waste of sulfur resources. The protocol provides a general method that is highly regio- and stereoselective for the synthesis of a diversity of tri- and tetrasubstituted alkenes.

CuI/glycerol mediated stereoselective synthesis of 1,2-bis-chalcogen alkenes from terminal alkynes: Synthesis of new antioxidants

(E)-1,2-Bis-chalcogen alkenes were stereoselectively prepared in good yields by the addition of diorganyl dichalcogenides to terminal alkynes using CuI/Zn/glycerol as a recyclable catalytic system. The antioxidant activity in vitro of four (E)-1,2-bis-cha

Highly stereoselective synthesis of 1,2-diorganothio-1-alkenes via hydrothiolation of alkynyl sulfides catalyzed by cesium hydroxide

In the presence of catalytic amount of cesium hydroxide, the hydrothiolation of alkynyl sulfides occurred at room temperature in DMF under nitrogen atmosphere to afford exclusive (Z)-1,2-diorganothio-1-alkene in excellent yields. It could provide a new an

Stereoselective synthesis of (Z)-1,2-diarylthio-1-alkene via the reaction of diaryl disulfides with terminal alkynes catalyzed by cesium hydroxide

In the presence of a catalytic amount of cesium hydroxide under a nitrogen atmosphere, terminal alkynes reacted with diaryl disulfides at room temperature in dimethylformamide to give almost exclusively (Z)-1,2-diarylthio-1-alkene in good yields, but unde

Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes

Novel transition-metal-catalyzed reactions of disulfides and diselenides with acetylenes are described. In the presence of tetrakis(triphenylphosphine)palladium(0), [Pd(PPh3)4], the (1) of diaryl disulfides and diselenides to terminal acetylenes 1 takes place stereoselectively to give high yields of (Z)-1,2-bis(arylthio)-1-alkenes 2 and (Z)-1,2-bis(arylseleno)-1-alkenes 3 respectively A mechanistic proposal includes the following: (1) oxidative addition of (ArY)2 [Y = S, Se] to low-valent palladium species, (2) stereoselective cis-thiopalladation or cis-selenopalladation to acetylenes to form a cis-vinylpalladium intermediate and (3) reductive elimination of the product with retention of the stereochemistry. When the reaction of diaryl disulfides and diselenides with terminal acetylenes is performed under the pressure of carbon monoxide, the carbonylative addition occurs to afford (Z)-1,3-bis(arylthio)-2-alken-1-ones 4 and (Z)-1,3-bis(arylseleno)-2-alken-1-ones 5, respectively. Carbon monoxide is regioselectively incorporated on the side of the terminal carbon of the acetylenes.

Synthesis of 2-(Trimethylsilyl)ethyl Benzenesulfenate and Benzeneselenenate and Their Reaction with Some Electrophiles in the Presence of Tetrabutylammonium Fluoride

2-(Trimethylsilyl)ethyl benzenesulfenate was allowed to react with several halides in the presence of tetrabutylammonium fluoride (TBAF) to afford the corresponding phenyl sulfoxides as the main product.In the reaction of 2-(trimethylsilyl)ethyl benzeneselenenate and several halides with TBAF, the corresponding alcohols were obtained as the main product.

ELECTROPHILIC ADDITION OF 4'-NITROBENZENESULPHENANILIDE TO ALKYNES, EFFECTS OF ARYL AND ALKYL SUBSTITUENTS AT RING CARBONS OF INTERMEDIATE THIIRENIUM IONS

The BF3-promoted addition of 4'-nitrobenzenesulphenanilide, NBSA, to a number of aryl- and alkyl-acetylenes has been investigated in dichloromethane, p-xylene and/or benzene.Diphenylacetylene, 1a, 1-phenylbutyne, 1b, and 1-phenylpropyne, 1c, generally lead to 1,2-bis(phenylthio)alkenes 4a-c, and N-(4-nitrophenyl)-S-phenyl-S-(2-phenylthiovinyl)sulphimides, 6a-c, in fair to good yields with trans stereospecificity.Phenylacetylene, 1d, similarly gives the corresponding bis(phenylthio)adduct 4d and sulphimide 6d in dichloromethane, but in the aromatic solvents these products are essentially suppressed in favour of 1-aryl-1-phenyl-2-(phenylthio)ethylenes 7d.On the other hand, alkyl- and, particularly, dialkyl-substituted acetylenes preferentially afford β-fluorovinyl sulphides, 5, with trans stereospecifity.These findings are interpreted in terms of a different reactivity towards nucleophilic attack of the intermediate aryl- and alkyl-trihirenium ions which would result from electrophilic sulphenylation of the corresponding alkynes.Steric effects of the substituents are believed to play a major role in determining the different reactivity observed.