- Cathodic Synthesis of Dicyanodiphenyl Diselenide From Phenylselenobenzonitrile
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The catodic reduction of 2-, 3- and 4-(phenylseleno)benzonitrile has been carried out in N,N-dimethylformamide and acetonitrile, at mercury, Pt, and glassy carbon electrodes.The first reduction step is accompanied by C-Se bond breaking.In the presence of an acid (fluorene, phenol, Bu4NSO4H), cyanobenzeneselenolate anions are thus generated in high yields, together with a small amount of benzeneselenolate anions (about 85percent and 15percent yiels, respectively).The former anions can be oxidised either anodically or chemically by air in alkaline aqueous solutions, and so 2,2'-, 3,3'- and 4,4'-dicyanodiphenyldiselenide are isolated in 59percent, 70percent and 75percent yields, respectively.
- Degrand, Chantal,Gautier, Christine,Kharroubi, Mohamed
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- Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy
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DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (~1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.
- Lin, Bizhen,Lu, Weiwei,Chen, Zhen-Yu,Zhang, Yue,Duan, Yin-Zhe,Lu, Xiaojie,Yan, Ming,Zhang, Xue-Jing
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supporting information
p. 7381 - 7385
(2021/10/12)
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- Metal-free synthesis of unsymmetrical selenides from pyridinium salts and diselenides catalysed by visible light
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We report the first metal-free selenolations of pyridinium salts with diselenides to prepare unsymmetrical organoselenides catalysed by visible light. This protocol is an efficient and green method for the preparation of unsymmetrical organoselenides because metal-free conditions and readily accessible diselenides are used.
- Ji, Liangshuo,Qiao, Jiamin,Li, Ankun,Jiang, Zeyi,Lu, Kui,Zhao, Xia
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supporting information
(2021/05/04)
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