104755-31-9Relevant articles and documents
Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals
Das, Sanju,Mandal, Tanumoy,De Sarkar, Suman
, p. 755 - 765 (2021/12/10)
A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.
Visible-light-induced oxidative coupling of vinylarenes with diselenides leading to α-aryl and α-alkyl selenomethyl ketones
Liu, Gong-Qing,Yi, Wei,Wang, Peng-Fei,Liu, Ji,Ma, Meng,Hao, Da-Yun,Ming, Liang,Ling, Yong
, p. 1840 - 1846 (2021/03/09)
A visible-light-induced oxidative coupling of diselenides with readily available vinylarenes is demonstrated. This benign protocol allows one to access a wide range of α-aryl and α-alkyl selenomethyl ketones in good yields with excellent functional group compatibility. The distinct advantages of this protocol over all previous methods include the use of a green solvent and air as an oxidant and the lack of a photocatalyst, a base, and an oxidant as well as better green chemistry matrices. Furthermore, the title reaction can be performed with natural sunlight, the most sustainable energy source imaginable. Additionally, the mild reaction conditions, easy operation and suitability for the modification of styrene-functionalized biomolecules make the current reaction system a more attractive method for the synthesis of a variety of medicinal and agrochemical compounds of interest.
Visible light promoted alpha-selenoketone compound synthesis method
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Paragraph 0055-0058, (2020/07/12)
The invention discloses a visible light promoted alpha-selenoketone compound synthesis method. The method comprises the following steps: A, sequentially adding compounds 1 and 2 into a reactor under an open condition; B, carrying out stirring reaction under a certain temperature condition and light source irradiation; C, after the reaction is finished, evaporating the solvent under reduced pressure to obtain a crude product; and D, carrying out column chromatography purification to obtain alpha-selenoketone 3. According to the preparation method, olefin and diselenide are used as the raw materials, one of acetonitrile, dichloromethane and ethyl acetate is used as a solvent, the reaction temperature is room temperature, the alpha-selenoketone compound is efficiently synthesized under irradiation of a white fluorescence light source, and compared with a traditional synthesis method, the method has the advantages that the reaction condition is mild, and the method can be smoothly carriedout at room temperature; the operation is simple, and all operations can be carried out in an open system; meanwhile, the method avoids using expensive transition metal catalysts, and has the characteristics of economy, green and environmental protection and the like.
Cesium carbonate-Catalyzed α-phenylchalcogenation of carbonyl compounds with diphenyl dichalcogenide
Nishiyama, Yutaka,Koguma, Yuya,Tanaka, Toshimasa,Umeda, Rui
experimental part, p. 3367 - 3375 (2009/12/24)
It was found that cesium carbonate has a unique catalytic ability on the reaction of carbonyl compounds with diphenyl diselenide to give the corresponding α-phenylseleno carbonyl compounds in moderate to good yields. Similarly, the α-phenylthiolation of c
Phenyl tributylstannyl selenide as a promising reagent for introducion of the phenylseleno group
Nishiyama, Yutaka,Kawamatsu, Hiroaki,Funato, Saori,Tokunaga, Keiji,Sonoda, Noboru
, p. 3599 - 3602 (2007/10/03)
A new synthetic method of organoselenium compounds has been developed. When phenyl tributylstannyl selenide (PhSeSnBu3) was allowed to react with acyl or aroyl chlorides in the presence of a catalytic amount of a palladium complex such as Pd(PPh3)4, Se-phenyl selenol esters were obtained in moderate to good yields. Similarly, the palladium complex catalyzed the reaction of PhSeSnBu3 with α-halo carbonyl compounds to afford the corresponding α-phenyseleno carbonyl compounds in moderate yields.
PHENYL SELENIUM TRICHLORIDE IN SYNTHESIS. REACTION WITH KETONES. A NEW VARIATION OF THE SELENOXIDE ELIMINATION REACTION
Engman, Lars
, p. 6385 - 6388 (2007/10/02)
Phenyl selenium trichloride was used for the introduction of a PhSeCl2-group into the α-position of ketones.These products were converted to enones (hydrolysis/selenoxide elimination) or α-phenylselenoketones (thiourea-reduction).
