62212-22-0Relevant articles and documents
Synthesis of Dibenzylic Diselenides from Elemental Selenium and Benzylic Quaternary Ammonium Salts
Chen, Feng,Li, Fuhai,Zeng, Qingle
, p. 5605 - 5608 (2021/11/11)
Abstract: Substituted dibenzyl diselenides are synthesized in good yields (74–91 %) by SN2 nucleophilic substitution of benzylic trimethylammonium salts and diselenide dianion (Se2?), in situ generated from elemental selenium, under
Toward Enantiomerically Pure β-Seleno-α-amino Acids via Stereoselective Se-Michael Additions to Chiral Dehydroalanines
Oroz, Paula,Navo, Claudio D.,Avenoza, Alberto,Busto, Jesús H.,Corzana, Francisco,Jiménez-Osés, Gonzalo,Peregrina, Jesús M.
supporting information, p. 1955 - 1959 (2021/01/13)
The first totally chemo- and diastereoselective 1,4-conjugate additions of Se-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. The methodology is simple and does not require any catalyst, providing exceptional yields at room temperature, and involves the treatment of the corresponding diselenide compound with NaBH4 in the presence of the Dha. These Se-Michael additions provide an excellent channel for the synthesis of enantiomerically pure selenocysteine (Sec) derivatives, which pose high potential for chemical biology applications.
Multistep Synthesis of Organic Selenides under Visible Light Irradiation: A Continuous-Flow Approach
Heredia, Adrián A.,Soria-Castro, Silvia M.,Castro-Godoy, Willber D.,Lemir, Ignacio D.,López-Vidal, Martín,Bisogno, Fabricio R.,Argüello, Juan E.,Oksdath-Mansilla, Gabriela
supporting information, p. 540 - 545 (2020/03/26)
The potential application of multistep continuous-flow systems has had a great impact on the syntheses of active pharmaceutical ingredients, natural products, and commodity chemicals. In this report, the highly efficient combination of a chemical reduction and a photochemical Csp2-H activation reaction for selenylation of biologically relevant electron-rich arenes was achieved by means of a continuous-flow process. First, the reduction of alkyl and aryl selenocyanates by Rongalite was achieved giving the corresponding diselenides; second, the photoactivation of the Se-Se bond resulted in the selenylation of electron-rich arenes, both steps from good to excellent yields. In all cases, the reaction time was shortened, and isolated yields were improved when compared to batch reaction conditions. Furthermore, connecting both reactions in a multistep continuous-flow sequence was possible even when reductive and photooxidative transformations were coupled.