61759-13-5Relevant articles and documents
Preparation of selenofunctionalized heterocycles via iodosobenzene-mediated intramolecular selenocyclizations of olefins with diselenides
Wang, Peng-Fei,Yi, Wei,Ling, Yong,Ming, Liang,Liu, Gong-Qing,Zhao, Yu
supporting information, p. 2587 - 2591 (2021/03/15)
An intramolecular selenocyclizations of olefins mediated by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provided access to a wide range of selenenylated heterocycles under ambient conditions. The striking advantages of this protocol over all previous methods include mild reaction conditions, easy operation, good yields, high levels of functional group compatibility, large–scale application and suitability for the late-stage functionalization of complex molecules of biological importance.
K2S2O8-promoted C-Se bond formation to construct α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds
Yang, Xue-Yan,Wang, Ruizhe,Wang, Lu,Li, Jianjun,Mao, Shuai,Zhang, San-Qi,Chen, Nanzheng
, p. 28902 - 28905 (2020/08/25)
A novel K2S2O8-promoted C-Se bond formation from cross-coupling under neutral conditions has been developed. A variety of aldehydes and ketones react well using K2S2O8 as the oxidant in the absence of catalyst and afford desired products in moderate to excellent yields. This protocol provides a very simple route for the synthesis of α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds.
O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol
Temperini, Andrea,Siciliano, Carlo
, (2020/06/17)
A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.
Air-stable binuclear Titanium(IV) salophen perfluorobutanesulfonate with zinc power catalytic system and its application to C–S and C–Se bond formation
Wang, Lingxiao,Qiao, Jie,Wei, Jiancong,Liang, Zhiwu,Xu, Xinhua,Li, Ningbo
, (2020/01/08)
An air-stable μ-oxo-bridged binuclear Lewis acid of titanium(IV) salophen perfluorobutanesulfonate [{Ti(salophen)H2O}2O][OSO2C4F9]2 (1) was successfully synthesized by the reaction of TiIV(salophen)Cl2 with AgOSO2C4F9 and characterized by techniques such as IR, NMR and HRMS. This complex was stable open to air over a year, and exhibited good thermal stability and high solubility in polar organic solvents. The complex also had relatively strong acidity with a strength of 0.8 Ho ≤ 3.3, and showed high catalytic efficiency towards various C–S and C–Se bond formations in the presence of zinc power. This catalytic system affords a mild and efficient approach to synthesis of thio- and selenoesters, α-arylthio- and seleno-carbonyl compounds, and thio- and selenoethers.
Rhodium-Catalyzed Rearrangement of S/Se-Ylides for the Synthesis of Substituted Vinylogous Carbonates
Reddy, Angula Chandra Shekar,Anbarasan, Pazhamalai
supporting information, p. 9965 - 9969 (2019/12/24)
An efficient rhodium-catalyzed unprecedented oxa-[2,3]-sigmatropic rearrangement of sulfur ylide derived from α-thioesters/ketones and diazo carbonyl compounds has been accomplished for the synthesis of various sulfur-tethered vinylogous carbonates in good to excellent yields. Important features of the developed reaction include wide functional group tolerance, excellent chemo- and regioselectivity, and efficient rearrangement involving the carbonyl motif. The present reaction also equally works well with α-selenoesters for the synthesis of seleno-containing vinylogous carbonates.
α-Organylchalcogenation of aldehydes and ketones with diorganyl dichalcogenides promoted by K3PO4
Movassagh, Barahman,Yousefi, Ali
, p. 1173 - 1177 (2014/06/24)
A new catalytic method for direct α-organylchalcogenation of aldehydes and ketones has been developed. When various aldehydes and ketones were allowed to react with diorganyl dichalcogenides in the presence of K 3PO4, under mild reac
α-Phenylselenenylation of aldehydes and ketones with diphenyl diselenide mediated by KF/Al2O3
Nazari, Mohammad,Movassagh, Barahman
experimental part, p. 1453 - 1455 (2009/05/31)
The utility of KF/Al2O3 for the synthesis of α-phenylseleno aldehydes and ketones from the corresponding aldehydes or ketones and diphenyl diselenide has been investigated. Simple stirring of a mixture of aldehyde or ketone and diphe
Synthesis of selenium-substituted pyrroles and pyrazol-3-ones
Attanasi, Orazio A.,De Crescentini, Lucia,Mantellini, Fabio,Marini, Francesca,Nicolini, Simona,Sternativo, Silvia,Tiecco, Marcello
experimental part, p. 1118 - 1122 (2011/04/15)
An approach to the synthesis of 4-(phenylseleno)pyrroles, 4-(phenylseleno)pyrazol-3-ones, and 4-(1,3-benzoselenazol-2-ylthio)pyrazol-3- ones is described. Their formation passes through hydrazonic intermediates obtained by the reaction between 1,2-diaza-1
ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS
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Page/Page column 53-54; 102, (2010/02/15)
The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo--selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R", NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ("hydrocarbyl") group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R" are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R" form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R" are attached; and wherein said compound is free from a metal catalyst.
Direct, facile aldehyde and ketone α-selenenylation reactions promoted by L-prolinamide and pyrrolidine sulfonamide organocatalysts
Wang, Jian,Li, Hao,Mei, Yujiang,Lou, Bihshow,Xu, Dingguo,Xie, Daiqian,Guo, Hua,Wang, Wei
, p. 5678 - 5687 (2007/10/03)
A new catalytic method for direct α-selenenylation reactions of aldehydes and ketones has been developed. The results of exploratory studies have demonstrated that L-prolinamide is an effective catalyst for α-selenenylation reactions of aldehydes, whereas
