24946-01-8Relevant articles and documents
Iodosobenzene-Mediated Three-Component Selenofunctionalization of Olefins
Liang, Zhi-Peng,Yi, Wei,Wang, Peng-Fei,Liu, Gong-Qing,Ling, Yong
, p. 5292 - 5304 (2021/04/06)
A three-component reaction of olefin, diselenide and water, alcohols, phenol, carboxylic acid, or amine by a commercially available hypervalent iodine(III) reagent, PhIO, was developed. This method provides access to a wide range of vicinally functionalized selenoderivatives under ambient conditions with mostly excellent yields and high diastereoselectivity. The developed reaction displays high levels of functional group compatibility and is suitable for the late-stage functionalization of styrene-functionalized biomolecules. Preliminary investigations on the mechanism of the reaction are also presented.
Meyer-Schuster-Type Rearrangement of Propargylic Alcohols into α-Selenoenals and -enones with Diselenides
Ban, Yong-Liang,You, Long,Feng, Kai-Wen,Ma, Fei-Cen,Jin, Xiao-Ling,Liu, Qiang
, p. 5274 - 5283 (2021/04/06)
We describe a mild and broadly applicable protocol for the preparation of a diverse array of multisubstituted α-selenoenals and -enones from readily accessible propargylic alcohols and diselenides. The transformation proceeds via the Selectfluor-promoted selenirenium pathway, which enables selenenylation/rearrangement of a variety of propargylic alcohols. Gram-scale experiments showed the potential of this synergistic protocol for practical application.
Efficient Protocol for Synthesis of β-Hydroxy(alkoxy)selenides via Electrochemical Iodide-Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides
Chen, Jinyang,Mei, Lan,Wang, Haiying,Hu, Li,Sun, Xiaorui,Shi, Jianwei,Li, Qiang
, p. 1230 - 1234 (2019/09/17)
An efficient protocol for the synthesis of β-hydroxy(alkoxy)selenides was developed through the electrochemical iodide-catalyzed oxyselenation of styrene derivatives with dialkyl(aryl)diselenides under mild reaction conditions. Mechanistic studies showed that the cation I+ is involved during the whole process, and accelerates the formation of seleniranium ion via substitution and addition reaction with dialkyl(aryl)diselenides and styrene derivatives. The corresponding products are formed in good to excellent yields. This electrochemical oxyselenation provides an efficient strategy for difunctionalization of alkenes.
Synthesis of 2,2-diarylvinyl phenyl selenides by dehydration of 2-hydroxyalkyl phenyl selenides
Stuhr-Hansen, Nicolai
, (2018/10/20)
A novel route to 2,2-diarylvinyl phenyl selenides is reported by dehydration of the corresponding 2,2-diaryl-2-hydroxyethyl phenyl selenides, prepared by oxyphenylselenenylations of the corresponding 1,1-diarylethylenes, upon treatment with p-toluenesulfonic acid.
Acidic hierarchical zeolite ZSM-5 supported Ru catalyst with high activity and selectivity in the seleno-functionalization of alkenes
Dong, Hai,Zhang, Lei,Fang, Zhongxue,Fu, Wenqian,Tang, Ting,Feng, Yu,Tang, Tiandi
, p. 22008 - 22016 (2017/07/10)
The acidic hierarchical zeolite ZSM-5 (HZSM-5-H) was synthesized for the preparation of a supported Ru catalyst (Ru/HZSM-5-H). The obtained Ru/HZSM-5-H catalyst shows high activity and product selectivity in the seleno-functionalization of alkenes compared to γ-Al2O3, basic ETS-10 and acidic microporous zeolite ZSM-5 supported Ru catalysts (Ru/γ-Al2O3, Ru/ETS-10 and Ru/HZSM-5, respectively), as well as a homogeneous RuCl3 catalyst. The relatively strong acidic sites in Ru/HZSM-5-H could benefit the adsorption of styrenes and the activation of the CC bond. Meanwhile, Ru4+ in Ru/HZSM-5-H could facilitate the formation of electrophilic selenium species as compared to Ru0 species. In addition, the Ru/HZSM-5-M catalyst exhibits broad substrate compatibility in the difunctionalization of alkenes.
Regioselective hydroxyselenation of styrenes by diselenides using the Zn/AlCl3 System
Movassagh, Barahman,Farshbaf, Sepideh
experimental part, p. 33 - 35 (2010/04/26)
A facile, zinc/aluminum(III) chloride promoted highly regioselective one-pot procedure has been developed for the preparation of β-hydroxy selenides from various styrenes and diselenides by Se-Se bond cleavage using the Zn/AlCl3 system in aqueo
THE REACTION O DIPHENYL DISELENIDE WITH PEROXYDISULPHATE IONS IN METHANOL A CONVENIENT PROCEDURE TO EECT THE METHOXYSELENENYLATION O ALKENES
Tiecco, M.,Testaerri, L.,Tingoli, M.,Chianelli, D.,Bartoli, D.
, p. 1417 - 1420 (2007/10/02)
Methoxyselenenylation of several alkenes was efected, in one step, by oxidation of diphenyl diselenide with ammonium peroxydisulphate in methanol.
ANODIC PHENYLSELENYLATION OF ASYMMETRIC OLEFINS
Latypova, V. Z.,Zhuikov, V. V.,Berestovitskaya, V. M.,Kargin, Yu. M.
, p. 1517 - 1519 (2007/10/02)
The anodic phenylselenylation of asymmetric olefins is accompanied by vicinal addition of the active nucleophilic components (water, acetonitrile) at most substituted carbon atoms of the multiple bond.
PHOTOINDUCED REACTIONS OF 3β-ACETOXYCHOLESTA-5,7-DIENE, 3β-ACETOXYCHOLEST-5-ENE, TETRAPHENYLCYCLOPENTADIENE AND 1,1-DIPHENYLETHYLENE WITH OXYGEN IN THE PRESENCE OF PHENYLSELENYL BROMIDE
Haynes, Richard K.,Hilliker, Audrey E.
, p. 509 - 512 (2007/10/02)
Whereas PhSeBr under irradiation with O2 in CH2Cl2 at -78 deg C acts as a photoxygenation catalyst to convert 3β-acetoxycholesta-5,7-diene and tetraphenylcyclopentadiene into the corresponding endoperoxides, and 3β-acetoxycholest-5-ene into 3β-acetoxycholest-5-en-7-one and the corresponding alcohols, it reacts with 1,1-diphenylethylene to give mainly a bromohydrin; bromine radicals arising by photodissociation of the PhSeBr are implicated as the active intermediates.
