22077-56-1Relevant academic research and scientific papers
Synthesis of Diaryl Selenides via Palladium-Catalyzed Debenzylative Cross-Coupling of Aryl Benzyl Selenides with Aryl Bromides
Wang, Hao,Chen, Shuguang,Liu, Guoqing,Guan, Haixing,Zhong, Daoyin,Cai, Jun,Zheng, Zhipeng,Mao, Jianyou,Walsh, Patrick J.
supporting information, p. 4086 - 4091 (2018/11/21)
Herein, we report a novel method for synthesizing diaryl selenides from aryl benzyl selenides and aryl bromides via debenzylative cross-coupling with a Pd/NIXANTPHOS-catalyst. NIXANTPHOS outperformed other commonly used bi- and monodentate ligands examined in this novel transformation. This reaction system displays wide functional group tolerance and excellent substrate scope. The transformation broadens the scope of palladium-catalyzed debenzylative processes to use selenolate anions as a leaving group. Its potential for practical synthetic applications was demonstrated with the gram scale synthesis of 4-chlorophenyl phenyl selenide.
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 (2018/03/27)
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.
Diarylation of chalcogen elements using arylboronic acids via copper- or palladium-catalyzed oxidative coupling
Taniguchi, Nobukazu
, p. 5818 - 5823 (2016/08/30)
Transition metal-catalyzed diarylations of sulfur, selenium and tellurium were achieved using arylboronic acids in air. A copper-catalyzed reaction of sulfur or selenium efficiently yielded numerous symmetrical diaryl sulfides or selenides in the presence of NH4BF4. However, the diarylation of tellurium was not possible using this method, and required a palladium catalyst in the presence of KI and air for the reaction to proceed.
An efficient one-pot approach to selenides: CuI-catalyzed reactions of magnesium selenolate with aryl or alkyl halides
Gao, Fei,Tang, Yu,Lin, Hemei,Yang, Jun,Zhang, Yuanming
, p. 787 - 793 (2013/07/26)
An efficient one-pot route to symmetrical selenides in GC with yields from 13 to 94% has been developed by CuI catalyzing reactions of magnesium organoselenolates with aryl or alkyl halides under mild conditions. It is suggested that selenium could leave from PhSeMgBr to form other RSeMgBr with RMgBr based on experimental results. Although the leaving selenium causes low yield of unsymmetrical selenides and complex products, it offers a slowly releasing selenium source in preparation of nano metal selenides, and a potential leaving group in nucleophilic substitution. The role of excess magnesium is proposed.
A novel and efficient synthesis of selenides
Lin, He M.,Tang, Yu,Li, Zhi H.,Liu, Kun D.,Yang, Jun,Zhang, Yuan M.
experimental part, p. 146 - 156 (2012/09/21)
Under nitrogen atmosphere, a simple and efficient procedure for the synthesis of symmetrical selenides has been developed by the reaction of aryl or alkyl halides with magnesium (1.5 equiv) and elemental selenium (1.0 equiv) in the absence of catalyst and ligand in THF and toluene under reflux at 86°C. This protocol has been utilized for the synthesis of a variety of symmetrical selenides in good to excellent yields. ARKAT-USA, Inc.
Copper-catalyzed chalcogenation of aryl iodides via reduction of chalcogen elements by aluminum or magnesium
Taniguchi, Nobukazu
, p. 10510 - 10515,6 (2012/12/12)
Aluminum-induced copper-catalyzed coupling of aryl iodides with selenium or sulfur element could afford the corresponding diaryl selenides or sulfides in good yields. When magnesium chloride as an additive was employed, diaryl monoselenides and monosulfides were selectively obtained. On the contrary, the use of sodium carbonate produced diaryl diselenides and disulfides. The preparation of diaryl diselenides was necessary for magnesium as a reductant. Regrettably, tellurium was very low reactivity.
Synthesis of arylselenide ethers by photoinduced reactions of selenobenzamide, selenourea and selenocyanate anions with aryl halides
Bouchet, Lydia M.,Pe?é?ory, Alicia B.,Argüello, Juan E.
experimental part, p. 969 - 972 (2011/03/20)
Selenobenzamide (-SeCNH(Ph), 1), selenourea ( -SeCNH(NH2), 2) and selenocyanate (-SeCN, 3) anions afford areneselenolate ions (ArSe-) under photostimulation in the presence of tert-butoxide or 2-naphthoxide ions as electron donors (entrainment conditions) in DMSO. In a 'one-pot' procedure, ArSe- anions can be trapped by a subsequent aliphatic nucleophilic substitution giving aryl methyl selenides in good to excellent yields (67-100%). This simple approach is compatible with electron-donating and electron-withdrawing substituents, such as nitro and carbonyl groups.
Synthesis of diaryl selenides using the in situ reagent SeCl2
Zade, Sanjio S.,Panda, Snigdha,Singh, Harkesh B.,Wolmersh?user, Gotthelf
, p. 665 - 669 (2007/10/03)
Reactions of in situ prepared SeCl2 with Grignard reagents (prepared from bromobenzene, o-tolyl bromide, 2,6-dimethyl-4-tert-butyl-1- bromobenzene, and 1-bromo-2-methylnaphthalene) and dilithiated benzamides (prepared from N-phenyl, N-cyclohexyl, and N-isopropyl benzamide) are described.
Structural studies on diaryl selenide dihalides in solution: Molecular complex formation of substituted diphenyl selenides with bromine
Nakanishi, Waro?,Hayashi, Satoko,Kusuyama, Yoshiaki
, p. 262 - 270 (2007/10/03)
Diaryl selenides that yield molecular complexes (MC) with bromine are prepared by modulating the effective electronegativity of the selenium atom and the steric environment around the atom in diphenyl selenide (1) with various substituents at the 2-, 3- and/or 4-positions. Halogen induced 1H and 13C NMR chemical shifts of the diaryl selenides are examined. The chlorine and iodine adducts of the selenides are shown to be trigonal bipyramidal adducts (TB) and MC, respectively. In the case of bromine adducts, the structures of (3- and 4-YC6H4)2SeBr2 are demonstrated to be MC if Y is CN and NO2, contrary to the general rule: they are TB if Y is less electron-withdrawing than the ethoxycarbonyl group. The CN and NO2 groups increase the effective electronegativity of the Se atom in (3- and 4-YC6H4)2Se and do not give TB with bromine. The four chloro groups at all meta-positions in 1 are also effective for MC formation. However, 3,5-(O2N)2C6H3SeBr2Ph is TB. Ab initio MO calculations show that the structures of (3-O2NC6H4)2Se and 3,5-(O2N)2C6H3SePh are close to the C2 and C s symmetries, respectively, which reveals that the conformational change is also important when the structures of the bromine adducts are determined. The steric congestion must be more severe for TB formation than for MC formation. The structures of 2,6-Cl2C6H3- SeBr2C6H4Y-p (Y = H and Br) are MC, which shows that the steric effect of 2,6-Cl2C6H3 group is effective for MC formation. (2-MeC6H4)2SeBr2 and (2-ClC6H4)2SeBr2 are TB and MC, respectively: the electronic effect of the Cl group must play an additional role in the MC formation since the bulkiness of the Me and Cl groups are expected to be similar. The bromine adduct of (2,4,6-Me3C6H2)2Se is also concluded to be MC: the steric effect of the four Me groups at the ortho-positions is large enough to give MC with bromine. The oxidation potentials (Eox) of the diaryl selenides explain well the structures of the bromine adducts: the electronic effect is directly correlated with Eox and the importance of the steric effect has been brought into sharp relief by Eox. Results of MO calculations support the outline of the observations. The structural behavior of some halogen adducts such as 2,6-Cl2C6H3SeCl2C6H 4Y-p (TB: Y = H and Br) is also discussed in some detail.
Synthesis, crystal structure, and reactivity of new amino- and ammonio- selenuranes containing transannular Se-N bond from 5H,7H- dibenzo[b,g][1,5]selenazocines
Mima, Hisatomo,Fujihara, Hisashi,Furukawa, Naomichi
, p. 743 - 752 (2007/10/03)
The reaction of N-methyl-5H,7H-dibenzo[b,g][1,5]selenazocine Se-oxide 2 with SOCl2 gave the chloroammonioselenurane 3b which was further converted into the methyl- or phenyl- substituted ammonioselenurane (4 or 5) upon treatment with Me2/
