134904-99-7Relevant academic research and scientific papers
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 (2005)
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.
Highly stereoselective method to prepare bis-phenylchalcogen alkenes via addition of chalcogenolate to phenylseleno alkynes
Perin, Gelson,Borges, Elton L.,Alves, Diego
experimental part, p. 2066 - 2069 (2012/07/14)
The preparation of bis-phenylchalcogen alkenes starting from phenylseleno alkynes is described. The nucleophilic species of selenium, tellurium and sulfur were generated in situ from the reaction of the respective diphenyl dichalcogenide with NaBH4 in PEG-400 as solvent. The chalcogenolate anions were efficiently and selectively added to a variety of phenylselenoalkynes at mild conditions, furnishing the respective (Z)-1,2-bis-phenylchalcogen alkenes in good yields.
A simple and stereoselective synthesis of (Z)-1,2-bis-arylselanyl alkenes from alkynes using KF/Al2O3
Lara, Renata G.,Rosa, Paloma C.,Soares, Liane K.,Silva, Marcio S.,Jacob, Raquel G.,Perin, Gelson
, p. 10414 - 10418,5 (2012/12/12)
The title compounds were synthesized by a one-pot reaction of diaryl diselenides with terminal alkynes avoiding the previous preparation of arylselanyl alkynes. The reactions were performed under mild conditions with a range of terminal alkynes using KF/A
Palladium and platinum catalyzed hydroselenation of alkynes: Se-H vs Se-Se addition to C≡C bond
Ananikov, Valentine P.,Malyshev, Denis A.,Beletskaya, Irina P.,Aleksandrov, Grigory G.,Eremenko, Igor L.
, p. 162 - 172 (2007/10/03)
A mechanistic study of the hydroselenation of alkynes catalyzed by Pd(PPh3)4 and Pt(PPh3)4 has shown that the palladium complex gives products of both Se-H and Se-Se bond addition to the triple bond of alkynes, while the platinum complex selectively catalyzes Se-H bond addition. The key intermediate of PhSeH addition to the metal center, namely Pt(H)(SePh)(PPh3)2, was detected by 1H-NMR spectroscopy. The analogous palladium complex rapidly decomposes with evolution of molecular hydrogen. A convenient method was developed for the preparation of Markovnikov hydroselenation products H2C=C(SePh)R, and the scope of this reaction was investigated. The first X-ray structure of the Markovnikov product H2C=C(SePh)CH2N+ HMe2·HOOC=COO- is reported.
Mechanism of catalytic addition of benzeneselenol to alkynes
Ananikov,Malyshev,Beletskaya
, p. 1475 - 1478 (2007/10/03)
Addition of benzeneselenol to terminal alkynes HC≡CR, catalyzed by Pd(0) complexes, leads to formation of mixtures of mono- and bis(phenylseleno)alkenes, depending on the nature of the R substituent. Electron-donor groups (R = Bu, CH2OH, CH2NMe2) give rise to addition according to the Markownikoff rule, whereas from alkynes with electron-acceptor groups (R = Ph, COOMe) mixtures of products are formed as a result of side reactions. A probable reaction mechanism includes oxidative addition of benzeneselenol to the metal, alkyne insertion into the Pd-Se bond, and reductive elimination.
Indium(I) iodide-mediated chemio-, regio-, and stereoselective hydroselenation of 2-alkyn-1-ol derivatives
Do Rego Barros, Olga Soares,Lang, Ernesto Shulz,De Oliveira, Carlos Alberto Fernandes,Peppe, Clovis,Zeni, Gilson
, p. 7921 - 7923 (2007/10/03)
Indium(I) iodide efficiently promotes the chemio-, regio-, and stereoselective hydroselenation of 2-alkyn-1-ol derivatives with diphenyl diselenide to produce the Markovnikov adducts with stereochemistry corresponding to an anti addition of the selenol co
A Novel Thermal Addition of Diaryl Diselenides to Acetylenes
Ogawa, Akiya,Takami, Noriaki,Sekiguchi, Masahito,Yokoyama, Hiroshi,Kuniyasu, Hitoshi,et al.
, p. 2241 - 2242 (2007/10/02)
When diphenyl diselenide is heated at 150-180 deg C in the presence of acetylenes, an acetylene insertion reaction into the Se-Se bond of the diselenide takes place to provide vic-bis(phenylseleno)alkenes in moderate to high yields.
