35050-01-2Relevant academic research and scientific papers
A facile synthetic route to α-selenoketones promoted by SmI2 or SmI3
Ying, Taokai,Bao, Weiliang,Zhang, Yongmin
, p. 1517 - 1523 (1996)
α-Arylseleno or α-alkylselenoketones were synthesized by reactions of α-haloketones with RSeBr mediated by SmI2 or SmI3.
Three-component aminoselenation of alkenes: Via visible-light enabled Fe-catalysis
Huang, Binbin,Li, Yanan,Yang, Chao,Xia, Wujiong
, p. 2804 - 2809 (2020)
A visible-light-enabled, iron-catalyzed three-component reaction for difunctionalization of alkenes with amines and diselenides has been developed, wherein a photo-excitable Fe-amine complex is proposed as the key intermediate. This ligand- and base-free transformation proceeds smoothly under air atmosphere at room temperature and features broad substrate scope.
A novel route to the synthesis of α-arylselenosubstituted carbonyl compounds and nitriles
Beletskaya, Irina,Sigeev, Alexander,Peregudov, Alexander,Petrovskii, Pavel
, p. 1348 - 1349 (2005)
Activated alkyl halides such as α-halocarbonyl compounds and α-halonitriles easily react with tributyltin arylselenides both in fluoride-mediated reaction and without any additives. The former protocol gives corresponding selenides under the mild conditio
Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals
Das, Sanju,De Sarkar, Suman,Mandal, Tanumoy
supporting information, (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
supporting information, 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-induced intermolecular aminoselenation of alkenes
Ling, Yong,Liu, Gong-Qing,Liu, Ji,Wang, Peng-Fei,Yi, Wei,Zhang, Yun-Qian,Zhou, Chen-Fan
supporting information, p. 9968 - 9973 (2021/12/24)
An intermolecular aminoselenation of alkenes with sulfonimides and diselenides is achieved via a visible-light-induced three component reaction. A broad variety of aminoselenation products is accessible in good yields with excellent functional group compatibility. Additional features of this new protocol include being additive- and photocatalyst-free and the use of natural sunlight as well as suitability for the modification of styrene-functionalized biomolecules. Mechanistic investigations suggest that the transformation occurs through a sequence of radical additions and nucleophilic substitutions. This journal is
Synergistic Catalysis of Se and Cu for the Activation of α-H of Methyl Ketones with Molecular Oxygen/Alcohol to Produce α-Keto Acetals?
Chen, Chao,Cao, Zhicheng,Zhang, Xu,Li, Yiming,Yu, Lei,Jiang, Xuefeng
, p. 1045 - 1051 (2020/06/30)
Selenium and copper synergistically catalyzed the oxidation/alkoxylation of methyl ketones to synthesize α-keto acetals directly. Using O2 as oxidant and alcohol as solvent and alkoxylation reagent, the reaction is practical from industrial viewpoint. Mechanistic studies revealed that copper promoted the oxidation of organoselenium intermediates with O2 to allow the key rearrangement and selenoxide syn-elimination regenerating the catalytically active organoselenium species.
Stereo- and Regioselective Cu-Catalyzed Hydroboration of Alkynyl Chalcogenoethers
de Oliveira, Isadora M.,Esteves, Henrique A.,Darbem, Mariana P.,Sartorelli, Arthur,Correra, Thiago C.,Rodrigues-Oliveira, André F.,Pimenta, Daniel C.,Zukerman-Schpector, Julio,Manarin, Flávia,Stefani, Hélio A.
, p. 3545 - 3552 (2020/06/02)
A mild stereo- and regioselective Cu-catalyzed hydroboration method for the synthesis of (Z)-seleno-alkenyl boronates and (Z)-thio-alkenylboronates from internal alkynes in the presence of commercially available B2pin2 is presented. This highly selective transformation relies on the use of N-heterocyclic carbene (NHC) complex IPrCuCl as the active catalytic species. We also explore the functionalization of the alkenylboronates obtained via oxidation to give α-chalcogeno ketones, useful building blocks for the synthesis of more complex chalcogen-containing molecules.
Visible light promoted alpha-selenoketone compound synthesis method
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Paragraph 0047-0050, (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.
Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry
Senatore, Raffaele,Castoldi, Laura,Ielo, Laura,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 2685 - 2688 (2018/05/22)
Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prepare α-aryl- and α-alkyl seleno methylketones through a single chemical operation. No racemization events are observed in the presence of optically pure starting materials.
