1132-39-4Relevant articles and documents
New synthetic method of diorganyl selenides: Palladium-catalyzed reaction of PhSeSnBu3 with aryl and alkyl halides
Nishiyama, Yutaka,Tokunaga, Keiji,Sonoda, Noboru
, p. 1725 - 1727 (1999)
(formula presented) Palladium complexes such as Pd(PPh3)4 catalyzed the reaction of phenyl tributylstannyl selenide (PhSeSnBu3) with aryl and alkyl halides, giving the corresponding diaryl and alkylaryl selenides in moderate to good yields.
Deoxygenation and other photochemical reactions of aromatic selenoxides
McCulla, Ryan D.,Jenks, William S.
, p. 16058 - 16065 (2004)
Atomic oxygen O(3P) is a potent oxidant that has been well-studied in the gas phase. However, exploration of its reactivity in the condensed organic phase has been hampered by the lack of an appropriate source. Dibenzothiophene-S-oxide (DBTO) and related derivatives have been promoted as photochemical D(3P) sources but suffer from low quantum yields. Photolysis of dibenzoselenophene-Se-oxide (DBSeO) results in the formation of dibenzoselenophene and oxidized solvent in significantly higher quantum yields, ca. 0.1. The oxidation product ratios from toluene obtained from the photolysis of dibenzothiophene-S-oxide and the corresponding selenoxide are the same, strongly suggesting a common oxidizing intermediate, which is taken to be O(3P). An additional product, proposed to be the corresponding selenenic ester, is also observed under deoxygenated conditions. The photochemistry of diphenyl selenoxide includes a minor portion of oxidant-forming deoxygenation, in contrast to previous conclusions.
Ullmann-type C-Se Cross-Coupling in the Hydantoin Family: Synthesis, Mechanistic Studies, and Tests of Biological Activity
Beloglazkina, Elena K.,Finko, Alexander V.,Laikov, Dimitri N.,Majouga, Alexander G.,Skvortsov, Dmitry A.,Tafeenko, Victor A.,Vyhivskyi, Oleksandr,Zhirkina, Irina V.,Zyk, Nikolay V.
, p. 3160 - 3173 (2020)
An attractive strategy for C-Se bond formation by Ullmann-type copper(I)-promoted cross-coupling is developed. A wide range of aryliodides reacts with various disubstituted 2-selenohydantoins under mild conditions and provides Se-arylated imidazolines in moderate to high yields. Computational mechanistic studies show the oxidative addition/intramolecular reductive elimination likely to be the lowest-energy pathway. Cytotoxic activity of all 43 reaction products has been tested in vitro against MCF7 and A549 cancer cell lines with VA13 and MCF10a control cells.
Simple and efficient copper-catalyzed synthesis of symmetrical diaryl selenides from triarylbismuthanes and selenium under aerobic conditions
Matsumura, Mio,Kumagai, Hanae,Murata, Yuki,Kakusawa, Naoki,Yasuike, Shuji
, p. 11 - 16 (2016)
Symmetrical diaryl selenides were synthesized in moderate-to-excellent yields by Cu-catalyzed C(aryl)–Se bond formation followed by the reaction of triarylbismuthanes with elemental Se in the presence of Cu(OAc)2 and 1,10-phenanthroline (10 mol%) under aerobic conditions. This reaction proceeded efficiently: All the aryl groups on Bi were transferred to the coupling products.
A novel stereoselective preparation of various vinyl sulfide derivatives using β-alkylthioalkenylselenonium salts
Watanabe,Mori,Nagai,Iwamura,Iwama,Kataoka
, p. 8893 - 8898 (2000)
The treatment of alkynylselenonium salt and various thiophenol derivatives with a catalytic amount of triethylamine gave β-arylthioalkenylselenonium salts in good yields. The alkenylselenonium salts thus prepared reacted with nucleophiles such as acetylides, thiolates, and alkoxides to produce (Z)-β-arylthio-α-functionalized ethenes in high yields. The vinylselenonium salts bearing a hydroxy group on a β-side chain caused intramolecular cyclization upon treatment with sodium hydride to produce medium-membered heterocyclic compounds containing sulfur and oxygen atoms. The reactions giving (Z)-β-arylthio-α-functionalized ethenes would proceed via the formation of selenurane intermediates followed by the ligand coupling reaction.
Reduction Process in the Photostimulated Reaction of Benzeneselenate Ion with Haloarenes
Penenory, Alicia B.,Pierini, Adriana B.,Rossi, Roberto A.
, p. 3834 - 3835 (1984)
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Introduction of alkyl- or phenylseleno group by the ring opening of cyclic ethers using dialkyl- or alkylphenylselenium dibromide and sodium borohydride
Takanohashi,Funakoshi,Akabori
, p. 2733 - 2741 (1994)
The reaction of dialkyl- or alkylphenylselenium dibromide with cyclic ethers in the presence of sodium borohydride gave ω-hydroxyalkyl alkyl or phenyl selenides as the ring opening products of the cyclic ethers.
Eco-friendly cross-coupling of diaryl diselenides with aryl and alkyl bromides catalyzed by CuO nanopowder in ionic liquid
Singh, Devender,Alberto, Eduardo E.,Rodrigues, Oscar Endrigo Dorneles,Braga, Antonio Luiz
, p. 1521 - 1524 (2009)
An eco-friendly cross-coupling reaction of aryl and alkyl bromides with diselenides using a catalytic amount of CuO nanopowder as a catalyst and an ionic liquid as a recyclable solvent is reported. The system shows high efficiency to catalyze this transformation, and in a green fashion due to the recyclable approach and the non-residual design protocol. This procedure has been utilized for the synthesis of a variety of diaryl selenides in good to excellent yields from the readily available aryl and alkyl bromides and diselenides. The Royal Society of Chemistry 2009.
Sakaki,Oae
, p. 1003,1004 (1977)
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Waters
, p. 1077 (1938)
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NOVEL REDUCTION OF CHLORINE ADDUCTS OF ARYL AND ALKYL SELENIDES WITH DIMETHYL SULFOXIDE
Nakanishi, Waro,Sakaue, Akira,Ikeda, Yoshitsugu,Iwamura, Hiizu
, p. 33 - 34 (1983)
The adducts of chlorine with diaryl selenides such as selenanthrene, diphenyl selenide, and selenoxanthone have been found to be reduced to the corresponding selenides in dimethyl sulfoxide forming chloromethyl methyl sulfoxide and hydrogen chloride.Similarly, dimethyl selenide dichloride was reduced to dimethyl selenide in the presence of a base.
CsOH·H2O promoted areneselenenylation of aryl bromides and iodides
Varala, Ravi,Ramu, Enugala,Adapa, Srinivas R.
, p. 140 - 141 (2006)
We report a transition metal-free synthetic protocol for the cross-coupling reaction of aryl bromides and aryl iodides and diphenyl diselenide (Ph 2Se2) using CsOH·H2O as a base in DMSO at 110°C. Using this protocol, we show that a variety of diaryl selenides can be synthesized in moderate to good yields.
A convenient method for the preparation of diaryl tellurides and diaryl selenides
Chen,Qiu,Zhou
, p. 1729 - 1734 (1991)
Sodium hydrogen telluride or selenide reacts rapidly with aryldiazonium fluoborates to give the corresponding symmetric diaryl tellurides or selenides.
Ni nanoparticle-confined covalent organic polymer directed diaryl-selenides synthesis
Awasthi, Satish Kumar,Dixit, A. K.,Raghothama, S.,Yadav, Deepika
, p. 12266 - 12272 (2020)
The present work describes the preparation of a new covalent organic polymer (COP) and its application as a hetero support for diaryl selenides synthesis. A nitrogen rich COP (CGP) has been synthesized via SNAr reaction of cyanuric chloride with guanidinium hydrochloride. The successful confinement of COP with Ni nanoparticles through post-synthetic transformations (Ni?CGP) provides excellent catalytic activity for the transformation of aryl halides into diaryl selenides using elemental selenium powder. The synthetic transformations are well confirmed using various modern analytical and spectroscopic techniques which reveal high chemical and thermal durability. The N-rich framework of CGP fortifies the confinement of Ni NPs. Ni?CGP provides an efficient approach for diaryl selenides synthesis using a very cheap selenating reagent under water benign solvent conditions (DMSO?:?H2O) at room temperature with high reusability. Significantly, our work not only contributes the opportunity for developing economical and effective non-noble metal decorated COPs as heterogeneous catalysts, but also delivers an efficient approach to produce industrially important C-Se coupling products.
Green Synthesis of Diaryl Selenides from Arylboronic Acids and Arylseleninic Acids
Redon, Sébastien,Remusat, Vincent,Vanelle, Patrice
supporting information, p. 483 - 487 (2022/02/21)
A new method of deborylative selanylation using arylboronic acids and arylseleninic acids gave diaryl selenoethers and diarylselenoxide. The present approach requires only equimolar arylseleninic acid and led selectively to selenoethers or selenoxides depending on the solvent. The method is metal-free, base- or oxidant-free, efficient, and environmentally friendly.
Trichloroisocyanuric Acid-Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature
Sun, Nan,Zheng, Kai,Sun, Pengyuan,Chen, Yang,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 3577 - 3584 (2021/06/15)
A transition-metal-free method for the synthesis of arylselenides and aryltellurides has been established based on the oxidative cross-coupling between diorganyl dichalcogenides and aryl boronic acids. With trichloroisocyanuric acid as an oxidant, the reaction proceeded smoothly to afford the desired products in 45–97% yields at ambient temperature. Three reaction reagents used in this method are stoichiometric and the oxidation by-product isocyanuric acid can be easily isolated and recovered. Besides of arylboronic acids, aryl trifluoroborates and aryl trihydroxyborates salts are also able to perform this transformation. (Figure presented.).
