35050-01-2Relevant articles and documents
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.
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,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
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.
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.
