15642-76-9Relevant academic research and scientific papers
Chemoselective and metal-free reduction of α,β-unsaturated ketones by: In situ produced benzeneselenol from O -(tert -butyl) Se-phenyl selenocarbonate
Ballarotto, Marco,Siciliano, Carlo,Temperini, Andrea
, p. 33706 - 33717 (2020/10/22)
The carbon-carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use of toxic Se/CO mixture and NaSeH, or the smelly and air-sensitive benzeneselenol, is avoided. This journal is
"On-water" Michael-type addition reactions promoted by PhSeZnCl
Battistelli, Benedetta,Lorenzo, Testaferri,Tiecco, Marcello,Santi, Claudio
experimental part, p. 1848 - 1851 (2011/05/05)
In this communication we report that our reagent PhSeZnCl can be conveniently used to effect Michael addition like reactions of unsaturated ketones and electron-deficient alkynes, leading to synthetically useful β-seleno derivativesand vinyl selenides, respectively. The reactions are effected at room temperature in THF as well as under "on water" conditions. When the addition occurs on a triple bond, good stereoselectivity is observed, and the reaction shows a rate acceleration in water suspension. Copyright
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.
