137540-60-4

Upstream product

• 115-19-5 2-methyl-but-3-yn-2-ol 
• 882-33-7 diphenyldisulfane 
• 13596-95-7 2-methyl-4-(phenylthio)but-3-yn-2-ol 
• 108-98-5 thiophenol 
• 66003-76-7 Diphenyliodonium triflate 
• 59-88-1 phenylhydrazine hydrochloride 

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.

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.).

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

Highly stereoselective one-pot procedure to prepare bis- and tris-chalcogenide alkenes via addition of disulfides and diselenides to terminal alkynes

We present here the reaction of diorganoyl dichalcogenides with terminal alkynes under catalyst-free conditions, by a one-pot procedure, to prepare bis- and tris-chalcogenide alkenes selectively, avoiding the previous preparation of chalcogen alkynes. The reaction proceeded cleanly under mild reaction conditions, and the addition of dichalcogenides to alkynes occurred stereoselectively to give exclusively the corresponding Z isomers. We observed that the selectivity control was governed by the effective participation of the hydroxyl group from propargyl alcohols. In addition, the bis-chalcogenide alkenes were exclusively obtained with propargyl alcohol having the acidic hydroxyl group proton. Conversely, the alkynes with no potentially acidic hydroxyl group proton, at propargyl positons, gave exclusively the tris-chalcogenide alkenes.

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.