7304-91-8Relevant academic research and scientific papers
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.
Visible light-induced photodeoxygenation of polycyclic selenophene Se-oxides
Chintala, Satyanarayana M.,Throgmorton, John C.,Maness, Peter F.,McCulla, Ryan D.
supporting information, (2020/10/02)
Photodeoxygenation of dibenzothiophene S-oxide (DBTO) is believed to produce ground-state atomic oxygen [O(3P)] in solution. Compared with other reactive oxygen species (ROS), O(3P) is a unique oxidant as it is potent and selective. Derivatives of DBTO have been used as O(3P)-precursors to oxidize variety of molecules, including plasmid DNA, proteins, lipids, thiols, and other small organic molecules. Unfortunately, the photodeoxygenation of DBTO requires ultraviolet irradiation, which is not an ideal wavelength range for biological systems, and has a low quantum yield of approximately 0.003. In this work, benzo[b]naphtho[1,2-d]selenophene Se-oxide, benzo[b]naphtho[2,1-d]selenophene Se-oxide, dinaphtho[2,3-b:2’,3’-d]selenophene Se-oxide, and perylo[1,12-b,c,d]selenophene Se-oxide were synthesized, and their ability to utilize visible light for generating O(3P) was interrogated. Benzo[b]naphtho[1,2-d]selenophene Se-oxide produces O(3P) upon irradiation centered at 420 nm. Additionally, benzo[b]naphtho[1,2-d]selenophene Se-oxide, benzo[b]naphtho[2,1-d]selenophene Se-oxide, and dinaphtho[2,3-b:2’,3’-d]selenophene Se-oxide produce O(3P) when irradiated with UVA light and have quantum yields of photodeoxygenation ranging from 0.009 to 0.33. This work increases the utility of photodeoxygenation by extending the range of wavelengths that can be used to generate O(3P) in solution.
ORGANODIARYL SELENOXIDES AND PROCESS FOR PREPARATION THEREOF
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Paragraph 0129-0132, (2017/06/29)
Novel organodiaryl selenoxides and processes for preparation thereof, and use thereof as ligand in complexes.
Oxidation of sulfides using recyclable pseudocyclic benziodoxole triflate
Yoshimura, Akira,Zhdankin, Viktor V.
, p. 32 - 40 (2017/03/14)
A new pseudocyclic hypervalent iodine reagent, benziodoxole triflate (IBA-OTf, a complex of 2-iodosylbenzoic acid with trifluoromethanesulfonic acid), can be used as an efficient oxidant for selective oxidation of various organic sulfides to sulfoxides. This oxidation proceeds under mild condition to afford the corresponding sulfoxides in moderate to good yields without overoxidation. The reduced form of the hypervalent iodine reagent, 2-iodobenzoic acid, can be easily recovered from the reaction mixture in good yields by a simple acid-base liquid-liquid biphasic protocol. (Chemical Equation Presented).
Synthesis of 9-oxoselenoxanthenium and triarylselenonium hexafluorophosphates
Loskutov,Balina,Russkikh,Shelkovnikov
, p. 1093 - 1097 (2015/06/30)
The selenoxides forming 9-oxoselenoxanthenium and triaryl selenonium hexafluorophosphates via interaction with heptyl phenyl ether and anisole in the MeSO3H-P2O5 mixture followed by treatment with KPF6 have been obtained via selenoxantene-9-one and diphenyl selenide derivatives oxidation with m-chloroperoxybenzoic acid or hydrogen peroxide.
Lewis basic selenium catalyzed chloroamidation of olefins using nitriles as the nucleophiles
Tay, Daniel Weiliang,Tsoi, Ivan Tan,Er, Jun Cheng,Leung, Gulice Yiu Chung,Yeung, Ying-Yeung
, p. 1310 - 1313 (2013/04/24)
A Lewis base catalyzed chloroamidation of olefinic substrates was achieved using diphenyl selenide as the catalyst. The reaction conditions are mild and suitable for a wide range of substrates including those which are acid labile.
A general and efficient method to convert selenides into selenones by using HOF·CH3CN
Potash, Shay,Rozen, Shlomo
, p. 5574 - 5579 (2013/09/12)
A general route for the preparation of selenones (R2SeO 2) is presented. This task is achieved through the quick and high-yielding reaction of selenides (R2Se) with HOF·CH 3CN. The reaction tolerates some elusiv
Aqueous sodium hypochlorite mediated chemoselective oxidation of chalcogenides to monoxides and dioxides by microwave exposure
Khurana, Jitender,Nand, Bhaskara
experimental part, p. 906 - 909 (2011/01/08)
A solvent-free, rapid, and highly selective oxidation of sulfides, selenides, and tellurides (chalcogenides) to the corresponding monoxides (sulfoxides, selenoxides, and telluroxides) or the corresponding dioxides (sulfones, selenones, and tellurones) has been developed using aqueous sodium hypochlorite on solid supports by exposure to microwave. Chemoselectivity and quantitative yields have been attained in most cases.
Deoxygenation and other photochemical reactions of aromatic selenoxides
McCulla, Ryan D.,Jenks, William S.
, p. 16058 - 16065 (2007/10/03)
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.
Singlet oxygen oxidation of selenides to selenoxides
Krief, Alain,Lonez, Frédéric
, p. 6255 - 6257 (2007/10/03)
The presence of water and a carbonate proved to be highly beneficial for singlet oxygen oxidation of selenides to selenoxides.
