17774-38-8Relevant articles and documents
Method for synthesizing asymmetric selenide through selenol catalytic reaction
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Paragraph 0019-0026, (2021/07/09)
The invention discloses a method for synthesizing asymmetric selenide through selenol catalytic reaction. The method comprises the following steps: (1) sequentially adding anhydrous N, N-dimethylformamide, zinc chloride, phenylselenol, a strong base, halogenated hydrocarbon and a 4A molecular sieve into a reaction container; (2) stirring and reacting for 20-40 hours at normal temperature in an oxygen-free state; (3) filtering, and removing N, N-dimethylformamide and halogenated hydrocarbon to obtain a stock solution; and (4) diluting the stock solution obtained in the step (3) with diethyl ether, washing with water, drying, and distilling off the diethyl ether to obtain the asymmetric selenide. According to the method for synthesizing the asymmetric selenide provided by the invention, the low-proportion zinc chloride is adopted for reaction, so that the final product asymmetric selenide can be efficiently obtained with high yield; the method has the advantages that the use of cesium base, namely cesium hydroxide, which is not easy to commercialize or is very uneconomical is avoided, harsh reaction conditions are also avoided, the mild reaction conditions are adopted, the reaction time is greatly shortened, the atom economy is realized, and the yield of the finally obtained asymmetric selenide is relatively high.
Production of Alkyl Aryl Sulfides from Aromatic Disulfides and Alkyl Carboxylates via a Disilathiane–Disulfide Interchange Reaction
Nakajima, Takumi,Takano, Ken,Maeda, Hiromu,Ogiwara, Yohei,Sakai, Norio
supporting information, p. 4103 - 4107 (2021/11/10)
The results of this study show that disilathiane is an effective mediator in the synthesis of alkyl aryl sulfides with disulfides and alkyl carboxylates. Mechanistic studies suggest that disilathiane promotes cleavage of the sulfur–sulfur bond of disulfides to generate thiosilane as a key intermediate. Diselenides were also applicable to this transformation to produce the corresponding selenides.
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.
Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides
Sakai, Norio,Maeda, Hiromu,Ogiwara, Yohei
, p. 2323 - 2330 (2019/05/24)
A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.
Corey-Chaykovsky Cyclopropanation of Nitronaphthalenes: Access to Benzonorcaradienes and Related Systems
Antoniak, Damian,Barbasiewicz, Micha?
supporting information, p. 9320 - 9325 (2019/11/19)
Nitronaphthalene derivatives react as Michael acceptors in the Corey-Chaykovsky reaction with alkyl phenyl selenones and alkyl diphenyl sulfonium salts. Mechanistic studies reveal that sterically demanding substituents at the carbanionic center favor formation of cyclopropanes and suppress competitive β-elimination to the alkylated products. The transformation, demonstrated also on heterocyclic nitroquinoline and nitroindazolines, is an example of transition metal-free dearomatization method.
α-Alkylation of tertiary amines by C(sp3)–C(sp3) cross-coupling under redox neutral photocatalysis
Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana
supporting information, p. 4480 - 4483 (2016/09/14)
Direct α-alkylation of N-phenyl-tetrahydroisoquinoline with alkyl selenides of desired alkyl chain length and functionality is reported by photoredox catalysis. Construction of hexahydro pyrrolo- and pyrido-isoquinoline scaffolds along with indolines and tetrahydroquinolines is also described by intramolecular C(sp3)–C(sp3) cross-couplings.
Radical intermediates in the Zn-promoted Barbier-type alkylation of diphenyl diselenide in aqueous medium
Dos Anjos, Jose Ayron Lira,Bieber, Lothar Wilhelm
, p. 6492 - 6494,3 (2012/12/12)
The zinc promoted Barbier-type reaction of alkyl halides and diphenyl diselenide in aqueous medium leads to high yields of mixed selenides even in acidic medium. Especially the efficient formation of t-butylphenylselenide cannot be explained by nucleophil
Zn in ionic liquid: An efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters
Narayanaperumal, Senthil,Alberto, Eduardo E.,Gul, Kashif,Kawasoko, Cristiane Yuriko,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
experimental part, p. 4723 - 4730 (2011/06/27)
A straightforward and efficient methodology is described to synthesize structurally diverse diorganyl selenides, sulfides, seleno- and thioesters by using commercially available Zn dust in ionic liquid. Excellent yields were achieved under neutral conditions at room temperature in a short time. The solvent/ionic liquid is reusable and exhibited higher performance as compared with organic solvents.
Bimetallic system for the synthesis of diorganyl selenides and sulfides, chiral β-seleno amines, and seleno- and thioesters
Gul, Kashif,Narayanaperumal, Senthil,Dornelles, Luciano,Rodrigues, Oscar E.D.,Braga, Antonio Luiz
supporting information; experimental part, p. 3592 - 3596 (2011/07/31)
The bimetallic reagent Sn(II)/Cu(II) in [bmim]BF4 was efficiently used for the cleavage of diaryl diselenides and disulfides and reacts with a variety of organic substrates, such as organic halides, acid chlorides, and β-amino mesylates affording the diorganyl selenides and sulfides within very short reaction times, under mild conditions and with excellent yields, using BMIM-BF4 as a reusable solvent.
Synthesis of diorganyl selenides mediated by zinc in ionic liquid
Narayanaperumal, Senthil,Alberto, Eduardo E.,Gul, Kashif,Rodrigues, Oscar E. D.,Braga, Antonio L.
supporting information; experimental part, p. 3886 - 3889 (2010/07/05)
Figure presented A new approach for the synthesis of diorganyl selenides is described. By using economically attractive zinc dust in BMIM-BF4, a series of diorganyl selenides were efficiently achieved in excellent yields, under neutral reaction conditions. Compared to the usual organic solvents, BMIM-BF4 exhibited higher performance with the advantage to be reused up to five successive runs.
