137540-50-2Relevant academic research and scientific papers
Palladium-Catalyzed Carbonylative Lactonization of Propargyl Alcohols with Organic Dichalcogenides and Carbon Monoxide
Ogawa, Akiya,Kuniyasu, Hitoshi,Sonoda, Noboru,Hirao, Toshikazu
, p. 8361 - 8365 (2007/10/03)
The reaction of propargylic alcohols with diaryl disulfides and carbon monoxide in the presence of tetrakis(triphenylphosphine)palladium leads to a novel thiolative lactonization to afford β-(arylthio)-α,β,-unsaturated lactones in moderate to good yields.
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.
