53188-76-4Relevant academic research and scientific papers
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.
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.
Iodine-mediated regioselective hydroxyselenenylation of alkenes: Facile access to β-hydroxy selenides
Wang, Xian-Long,Li, Hong-Jie,Yan, Jie
supporting information, p. 479 - 481 (2017/09/06)
In the presence of molecular iodine, the reaction of alkenes with diselenides proceeds efficiently under air and at room temperature in mixed solvent MeCN/H2O, which affording β-hydroxy selenides with high regioselectivity and in good to excellent yields. This iodine-mediated vicinal difunctionalization of alkenes requires mild reaction conditions and is a simple procedure, which extends the synthetic application of molecular iodine in organic synthesis.
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
Preparation of the first bench-stable phenyl selenolate: An interesting "on water" nucleophilic reagent
Santi, Claudio,Santoro, Stefano,Battistelli, Benedetta,Testaferri, Lorenzo,Tiecco, Marcello
scheme or table, p. 5387 - 5390 (2009/05/07)
In this communication we report the synthesis and the characterization of the first solid and air-stable selenolates, starting from commercially available phenylselenenyl halides and elemental zinc. These reagents were efficiently employed in the ring ope
A novel synthetic approach to β-arylselenenyl tertiary alcohols by the one-pot reaction of chloromethyl selenides and ketones promoted by samarium diiodide
Huang, Xian,Duan, De-Hui
, p. 1191 - 1192 (2007/10/03)
At ambient temperature, β-arylselenenyl tertiary alcohols can be conveniently synthesized with samarium diiodide, chloromethyl selenides and ketones by one-pot method in high yields.
Oxidative Conversion of β-Hydroxyselenides to Epoxides and Ketones with meta-Chloroperbenzoic Acid
Uemura, Sakae,Ohe, Kouichi,Sugita, Nobuyuki
, p. 111 - 112 (2007/10/02)
Treatment of β-hydroxy-primary-alkyl and β-hydroxy-β-phenyl-primary-alkyl phenyl selenides with 3-5 equiv. of m-chloroperbenzoic acid in methanol or tetrahydrofuran gives the corresponding epoxides and phenyl migrated ketones, respectively in high yields.
OXIDATION OF SELENIDES TO SELENOXIDES USING 2-SULFONYLOXAZIRIDINES
Davis, Franklin A.,Stringer, Orum D.,Billmers, Joanne M.
, p. 1213 - 1216 (2007/10/02)
Application of 2-sulfonyloxaziridine, 9, for the "one-pot" transformation of selenides to alkenes and the rearrangement of allylic selenides to allylic alcohols are described.
One -step Oxidation of Olefins into α-Phenylseleno Carbonyl Compounds
Shimizu, Makoto,Kuwajima, Isao
, p. 3100 - 3105 (2007/10/02)
Oxidation of olefins has been examined with the following three types of reagents; (i) (C6H5Se)2-Br2-(Bu3Sn)2O, (ii) (C6H5Se)2-t-BuOOH, and (iii) (C6H5Se)2-(C6H5SeO)20, and the corresponding α-phenylseleno carbonyl compounds have been obtained directly from the olefins.
