51558-95-3Relevant academic research and scientific papers
Catalytic and Atom-Economic Intermolecular Amidoselenenylation of Alkenes
Tang,Wang, Weilin,Zhao, Yinjiao,Zhang, Meng,Dai, Xin
, p. 176 - 179 (2016)
A method for the simple, efficient, and atom-economic amidoselenenylation of simple alkenes under mild conditions using TiCl4 as a catalyst and N-(phenylseleno)phthalimide as both a nitrogen and selenium source was developed. A broad range of olefins can be applied to afford vicinal amidoselenides in good yield and with high regioselectivity and diastereoselectivity.
One-pot synthesis of vinyl phosphonates from 2-hydroxyalkyl phenyl selenides with monoethyl esters of phosphonic acid
Sheng, Shou-Ri,Sun, Wu-Kang,Hu, Ming-Gang,Liu, Xiao-Ling,Wang, Qiu-Ying
, p. 97 - 99 (2007)
Vinyl phosphonates were prepared with good yields in a one-pot, two-step transformation by Mitsunobu reaction of 2-hydroxyalkyl phenyl selenides with monoethyl esters of phosphonic acid followed by oxidation-elimination.
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.
Method for promoting synthesis of beta-hydroxyl selenide compound by visible light
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Paragraph 0046-0049, (2021/05/01)
The invention relates to the technical field of organic synthetic chemistry, in particular to a method for promoting synthesis of a beta-hydroxyl selenide compound by visible light. The method comprises the following steps: A, sequentially adding a compound 1 and a compound 2 into a reactor; B, stirring the compound 1 and the compound 2 for reaction at a certain temperature under the irradiation of a light source under an open condition; C, after the reaction is finished, evaporating the solvent under reduced pressure to obtain a crude product; and D, carrying out column chromatography purification to obtain the beta-hydroxy selenide compound 3. According to the method, olefin and diselenide are used as raw materials, one of an acetonitrile/water mixed solvent and an acetone/water mixed solvent is used as a solvent, the reaction temperature is room temperature, and the beta-hydroxyl selenide compound is efficiently synthesized under the irradiation of a white fluorescent light source; compared with the traditional synthesis method, the method has the advantages that the reaction conditions are mild and can be smoothly carried out at room temperature; operation is simple, and all operations can be carried out in an open system; and raw materials are easy to obtain, the yield is high, functional group compatibility is good, and the substrate application range is wide.
Synthesis of β-hydroxy aryl selenides via transition-metal-free three-component reaction of arylamines, elemental selenium, and epoxides
Wang, Hongwei,Li, Hongchen,Bai, Yalong,Hei, Yanling,Chen, Junwei,Yu, Guoqi,Zhou, Yun-Bing
, p. 3621 - 3629 (2021/06/21)
An efficient protocol for the construction of valuable β-hydroxy aryl selenides from easily available arylamines, elemental selenium, and epoxides through a transition-metal-free radical process is described. A wide variety of β-hydroxy aryl selenides were obtained in good to excellent yields with excellent stereo- and regioselectivity. In this reaction, two C-Se bonds can be built along with the cleavage of a C-N and C-O bond, demonstrating the high step economy and efficiency of this approach.
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.
Automated Electrochemical Selenenylations
Amri, Nasser,Wirth, Thomas
supporting information, p. 1751 - 1761 (2020/06/08)
Integrated electrochemical reactors in automated flow systems were utilised for selenenylation reactions. The automation allowed multiple electrochemical reactions of a programmed sequence to be performed in a fully autonomous way. Many functionalised selenenylated products were synthesised in short reaction times in good to high yields.
O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol
Temperini, Andrea,Siciliano, Carlo
, (2020/06/17)
A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.
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.
Electrochemical Aminoselenation and Oxyselenation of Styrenes with Hydrogen Evolution
Sun, Li,Yuan, Yong,Yao, Min,Wang, Han,Wang, Daoxin,Gao, Meng,Chen, Yi-Hung,Lei, Aiwen
supporting information, p. 1297 - 1300 (2019/02/19)
The use of additive-free conditions is an ideal approach to prepare organoselenium reagents from readily available unsaturated substrates. Thus, we report the electro-induced aminoselenation and oxyselenation of styrenes without any acids or oxidants as additives. This transformation is compatible with various functional groups, which leads to vicinal difunctionalized organoselenium compounds. Our strategy improves the potential of this protocol for use in the pharmaceutical industry. Based upon the preliminary mechanism studies, we propose two possible pathways.
