137540-63-7Relevant academic research and scientific papers
NMR approach for the identification of dinuclear and mononuclear complexes: The first detection of [Pd(SPh)2(PPh3)2] and [Pd2(SPh)4(PPh3)2] - The intermediate complexes in the ca
Ananikov, Valentine P.,Zalesskiy, Sergey S.,Kachala, Vadim V.,Beletskaya, Irina P.
, p. 400 - 405 (2011)
In the present study we have analyzed the nature of palladium complexes in the catalytic system for selective carbon-sulfur bond formation via the addition of S-S and S-H bonds to alkynes. For the first time the mononuclear and dinuclear palladium complex
The first example of polymer-supported palladium catalyst for stereo-selective S-S bond addition to terminal alkynes
Ananikov, Valentine P.,Kabeshov, Michael A.,Beletskaya, Irina P.
, p. 1015 - 1017 (2005)
The polymer-supported recyclable palladium catalyst was prepared for stereoselective diaryl disulphides addition to terminal alkynes with high yields. The 96-98% product purity was achieved after filtering the polymer-supported catalyst without special pu
Addition of diaryl disulfides to terminal alkynes catalysed by an MCM-41-supported bidentate phosphine palladium(0) complex
Li, Jianying,Liu, Jun,Cai, Mingzhong
experimental part, p. 616 - 618 (2011/02/26)
A variety of (Z)-1,2-bis(arylthio)-substituted alkenes have been conveniently synthesised in high yields by the stereoselective addition of diaryl disulfides to terminal alkynes catalysed by an MCM-41-supported bidentate phosphine palladium(0) complex. Th
Highly stereoselective one-pot procedure to prepare bis- and tris-chalcogenide alkenes via addition of disulfides and diselenides to terminal alkynes
Moro, Angelica Venturini,Nogueira, Cristina W.,Barbosa, Nilda B. V.,Menezes, Paulo Henrique,Teixeira Da Rocha, Joao Batista,Zeni, Gilson
, p. 5257 - 5268 (2007/10/03)
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 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.
