90454-87-8

Upstream product

• 1666-13-3 diphenyl diselenide 
• 118-92-3 anthranilic acid 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 100-58-3 phenylmagnesium bromide 
• 615-42-9 1,2-Diiodobenzene 
• 68395-76-6 1-amino-2-phenylselanylbenzene 
• 1614-12-6 1H-1,2,3-benzotriazol-1-amine 

Downstream Products

• 29372-65-4 1,2-bis(phenylselanyl)benzene tetrachloride 

Relevant academic research and scientific papers

The diorgano dichalcogenides addition to benzyne under mild conditions

The reaction between diorgano dichalcogenides and o-(trimethylsilyl)phenyl triflate in the presence of CsF at room temperature produced o-bis(organochalcogenide)benzenes in moderate to good yields.

Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent

Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C S bondformation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N'-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.

Catalytic Asymmetric Electrochemical α-Arylation of Cyclic β-Ketocarbonyls with Anodic Benzyne Intermediates

Asymmetric catalysis with benzyne remains elusive because of the highly fleeting and nonpolar nature of benzyne intermediates. Reported herein is an electrochemical approach for the oxidative generation of benzynes (cyclohexyne) and its successful merging with chiral primary aminocatalysis, formulating the first catalytic asymmetric enamine–benzyne (cyclohexyne) coupling reaction. Cobalt acetate was identified to stabilize the in situ generated arynes and facilitate its coupling with an enamine. This catalytic enamine-benzyne protocol provides a concise method for the construction of diverse α-aryl (α-cyclohexenyl) quaternary carbon stereogenic centers with good stereoselectivities.

Copper-catalyzed: Ipso -selenation of aromatic carboxylic acids

The copper-catalyzed decarboxylative selenation of aromatic carboxylic acids with diselenide is reported. This transformation tolerated a diverse set of functional groups on the substrates, including pentafluorobenzoic acid and heteroaromatic acids, delivering diaryl and methyl aryl selenides in good to excellent yields. Mechanistic studies indicated that the copper catalyst is essential in the activation of the Se-Se bond and the decarboxylation of aromatic acids. The utility of the products has been demonstrated in the facile synthesis of 10H-phenoselenazine and 11-methyldibenzo-(b,f)-1,4-selenazepine.

Magnetically separable and reusable copper ferrite nanoparticles for cross-coupling of aryl halides with diphenyl diselenide

A simple and efficient procedure for the synthesis of diaryl selenides has been developed by a copper ferrite nanoparticle catalyzed reaction of aryl iodides/aryl bromides with diphenyl diselenide in the presence of base and solvent at 120 °C. Using this protocol, a variety of diselenides were obtained in good to excellent yields. The copper ferrite nanoparticles were magnetically separated, recycled, and reused up to three cycles. Copyright

Selenium-Nitrogen Bond Cleavage in Selenazole Ring System with Grignard Reagent: A Convenient Synthesis of Unsymmetrically Substituted Selenides

High reactivity of the selenenamide bond in selenazoles toward nucleophiles can be exploited for synthesis of other organoselenium compounds. It has been found that benzisoselenazol-3(2H)-ones and related selenaheterocycles with an Se-N moiety treated with Grignard reagent gave unsymmetrical aryl-aryl and aryl-alkyl selenides in moderate to good yields. This reaction has a synthetic value because it is highly selective and can be realized under mild conditions.

Methods for formation of aryl-sulfur and aryl-selenium compounds using copper(I) catalysts

A mild, palladium-free synthetic protocol for the cross-coupling reaction of vinyl or aryl iodides and thiols or selenols using, in certain embodiments, 10 mol % CuI and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 ° C. A variety of vinyl/aryl sulfides and vinyl/aryl selenides can be synthesized in excellent yields from readily available iodides and thiols or selenols.

Inter-element linkage in 1,2- and 1,4-bis(arylselanyl)benzenes with halogens

The criteria to distinguish the structure of halogen adducts of aryl chalcogenides in solutions based on the NMR chemical shifts are confirmed by ab initio molecular orbitals (MO) calculations based on the gauge-including atomic orbitals (GIAO) theory. The criteria are applied to determine the structure of halogen adducts of 1,2-bis(phenylselanyl)benzene (1), 1,4-bis(phenylselanyl)benzene (2), and 1,4-bis(p-tert-butylphenylselanyl)benzene (3) (1·nX2, 2·nX2, and 3·nX2, respectively: n = 1 and 2 and X = Cl, Br, and I) in CDCl3. The structure of 1·Br2 is demonstrated to be trigonal bipyramidal (TB) not only in the solution but also in crystals. The TB formation of 1·Br2 is just the opposite of the MC (molecular complexes) formation of selenanthrene with bromine in the solution. The driving force for the TB and MC formation is discussed based on the structure of the parent selenides. The structure of 2·2X2 and 3·2X2 is (TB, TB) for X = Cl and Br and (MC, MC) for X = I. On the other hand, the structure of 1·2Br2 is revealed to be TB at one SeBr2 moiety but MC for the other SeBr2 group, which is described as (TB, MC). The bromine exchange is observed in 1·2Br2 in the conditions of NMR measurements. The rate of bromine exchange becomes sharp as excess bromine is added to the 1·2Br2 solution, which shows that the structural (TB, MC) ? (MC, TB) site exchange in 1·2Br2 is accelerated by the excess bromine and/or its derivatives. Ab initio MO calculations are performed on the adducts to understand their structural features and on the proposed intermediate to confirm the mechanism.

SYNTHESIS, PROPERTIES, AND MULTINUCLEAR (1H, 13C, 77Se) NUCLEAR MAGNETIC RESONANCE STUDIES OF SELENOETHERS CONTAINING TWO OR MORE SELENIUM ATOMS

A convenient synthesis of MeSeLi from MeLi and Se8 in tetrahydrofuran (THF) has been used to prepare the bis-selenoethers MeSenSeMe (n = 1,2,3,6, or 12) and cis-MeSeCH=CHSeMe.PhSenSePh (n = 1-3) and cis-PhSeCH=CHSePh have been prepared from PhSe-, itself produced from Ph2Se2 and LiALH4-THF or sodium hydroxymethanesulphinate.The bis-selenoethers o-C6H4(SeR)2 (R = Me or Ph) were obtained from R2Se2 and benzyne.The syntheses of (RSeCH2)3CMe (R = Me or Ph), (MeSeCH2)4C, and (MeSeCH2CH2CH2)2Se are also described.The 1H, 13C, and 77Se n.m.r. spectra of these selenoethers have been recorded, and the chemical shifts and coupling constants (nJSe-H, nJSe-C) are discussed in terms of structures.Mass spectra of the selenoethers have been recorded and the principle fragmentation modes identified.