109019-09-2Relevant articles and documents
CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids
Alves, Diego,Santos, Cayane G.,Paix?o, Márcio W.,Soares, Letiére C.,Souza, Diego de,Rodrigues, Oscar E.D.,Braga, Ant?nio L.
, p. 6635 - 6638 (2009)
We present here an efficient and ligand-free cross-coupling reaction of organic diselenides with aryl boronic acids using a catalytic amount of CuO nanoparticles in DMSO at 100 °C under air atmosphere. This is a general cross-coupling reaction and was performed with organic diselenides and aryl boronic acids bearing electron-withdrawing and electron-donating groups affording the corresponding selenides in good to excellent yields. The CuO nanoparticles can be easily recovered and utilized for further catalytic reactions.
Silver-Catalyzed Synthesis of Diaryl Selenides by Reaction of Diaryl Diselenides with Aryl Boronic Acids
Goldani, Bruna,Ricordi, Vanessa G.,Seus, Natália,Lenard?o, Eder J.,Schumacher, Ricardo F.,Alves, Diego
, p. 11472 - 11476 (2016)
We described herein our results on the silver-catalyzed synthesis of diaryl selenides via a cross-coupling reaction of diaryl diselenides with aryl boronic acids. The methodology is tolerant to electron-donor and electron-withdrawing groups at the substrates and the desired products were obtained in good to excellent yields.
Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids
Freitas, Camilo S.,Barcellos, Angelita M.,Ricordi, Vanessa G.,Pena, Jesus M.,Perin, Gelson,Jacob, Raquel G.,Lenardao, Eder J.,Alves, Diego
, p. 2931 - 2938 (2011)
We described herein the use of imidazolium ionic liquids [bmim]PF 6 and [bmim]BF4 in the selective, metal and catalyst-free synthesis of unsymmetrical diaryl selenides by electrophilic substitution in arylboron reagents with arylselenium halides (Cl and Br) at room temperature. This is a general substitution reaction and it was performed with arylboronic acids or potassium aryltrifluoroborates bearing electron-withdrawing or electron-donating groups, affording the corresponding diaryl selenides in good to excellent yields. The ionic liquid [bmim][PF6] was easily recovered and utilized for further substitution reactions.
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.).
Asymmetric Heteroleptic Ir(III) Phosphorescent Complexes with Aromatic Selenide and Selenophene Groups: Synthesis and Photophysical, Electrochemical, and Electrophosphorescent Behaviors
Feng, Zhao,Wang, Dezhi,Yang, Xiaolong,Jin, Deyuan,Zhong, Daokun,Liu, Boao,Zhou, Guijiang,Ma, Miaofeng,Wu, Zhaoxin
supporting information, p. 11027 - 11043 (2018/09/14)
With the aim of evaluating the potential of selenium-containing groups in developing electroluminescent (EL) materials, a series of asymmetric heteroleptic Ir(III) phosphorescent complexes (Ir-Se0F, Ir-Se1F, Ir-Se2F, and Ir-Se3F) have been synthesized by using 2-selenophenylpyridine and one ppy-type (ppy = 2-phenylpyridine) ligand with a fluorinated selenide group. To the best of our knowledge, these complexes represent unprecedented examples of asymmetric heteroleptic Ir(III) phosphorescent emitters bearing selenium-containing groups. Natural transition orbital (NTO) analysis based on optimized geometries of the first triplet state (T1) have shown that the phosphorescent emissions of these Ir(III) complexes dominantly show 3π- π? features of the 2-selenophenylpyridine ligand with slight metal to ligand charge transfer (MLCT) contribution. In comparison with their symmetric parent complex Ir-Se with two 2-selenophenylpyridine ligands, these asymmetric heteroleptic Ir(III) phosphorescent complexes can show much higher phosphorescent quantum yields (φP) of ca. 0.90. Both the hole- and electron-trapping ability of these Ir(III) phosphorescent complexes can be enhanced by selenophene and fluorinated selenide groups to improve their EL efficiencies. The EL abilities of these asymmetric heteroleptic Ir(III) phosphorescent emitters fall in the order Ir-Se3F > Ir-Se2F > Ir-Se1F > Ir-Se0F. The highest EL efficiencies have been achieved by Ir-Se3F in the solution-processed OLEDs with external quantum efficiency (next), current efficiency (n L), and power efficiency (n P) of 19.9%, 65.6 cd A-1, and 57.3 lm W-1, respectively. These encouraging EL results clearly indicate the great potential of selenium-containing groups in developing high-performance Ir(III) phosphorescent emitters.
