114221-65-7Relevant academic research and scientific papers
Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant
Wang, Jin,Wei, Chiyu,Li, Xuming,Zhao, Pengyi,Shan, Chuan,Wojtas, Lukasz,Chen, Hao,Shi, Xiaodong
supporting information, p. 5946 - 5950 (2020/04/23)
Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.
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
Cesium Salt-Catalyzed Addition of Diphenyl Dichalcogenides to Alkynes: Selective Synthesis of Bis- and Mono(phenylchalcogeno)alkenes
Nishiyama, Yutaka,Ohnishi, Haruko,Koguma, Yuya
experimental part, p. 1170 - 1174 (2009/12/25)
A cesium salt has a unique catalytic ability for the reaction of alkynes with diphenyl dichalcogenides. When the diphenyl dichalcogenides, such as the disulfide, diselenide, or ditelluride, were allowed to react with alkynes in the presence of a catalytic
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.
Free-Radical Additions of Diselenides to Dimethyl Acetylenedicarboxylate, Methyl Propiolate, and Dimethyl Maleate
Back, Thomas G.,Krishna, M. Vijaya
, p. 2533 - 2536 (2007/10/02)
The photolysis of diphenyl or dimesityl diselenide with dimethyl acetylenedicarboxylate or methyl propiolate resulted principally in the formation of the corresponding vicinal bisselenides 1a,b,2a,b, and 6a,b via a free-radical chain addition mechanism.Dimethyl maleate underwent a selenyl radical mediated isomerization to dimethyl fumarate when similarly photolyzed with diphenyl diselenide.
