137540-64-8Relevant academic research and scientific papers
Palladium-Catalyzed Regioselective Three-Component Cascade Bisthiolation of Terminal Alkynes
Li, Jianxiao,Li, Can,Ouyang, Lu,Li, Chunsheng,Yang, Shaorong,Wu, Wanqing,Jiang, Huanfeng
, p. 1138 - 1150 (2018/02/06)
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.).
Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes
Kuniyasu, Hitoshi,Ogawa, Akiya,Miyazaki, Shin-Ichiro,Ryu, Ilhyong,Kambe, Nobuaki,Sonoda, Noboru
, p. 9796 - 9803 (2007/10/02)
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.
