Stereoselective synthesis of E-2-halovinyl tellanes, ditellanes and selenides based on tellurium tetrahalides, selenium dihalides and internal alkynes

Потапов, В. А.; Мусалов, М. В.; Мусалова, М. В.; Rusakov, Yury Yu.; Хабибулина, А. Г.; Rusakova, Irina L.; Амосова, С. В.

doi:10.1016/j.jorganchem.2018.02.015

Cited by 16 publications

(8 citation statements)

References 41 publications

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“…Organotellurium compounds have served as important synthetic intermediates, and especially, diorganyl tellurides have been used as carbon nucleophile sources through a tellurium‐lithium exchange reaction . In addition, a relatively weaker carbon–tellurium bond (48 kcal/mol) makes organotellurium compounds fascinating in radical chemistry .…”

Section: Introductionmentioning

confidence: 99%

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Yamamoto

Sato

Kodama

et al. 2018

Heteroatom Chemistry

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The reactivity of diaryl ditelluride and diaryl telluride toward aryl radicals was studied in detail. Diphenyl ditelluride underwent a bimolecular homolytic substitution (SH2) reaction with a phenyl radical generated from phenylhydrazine in the air, to afford diphenyl telluride in excellent yield. Based on this diphenyl telluride synthesis, a one‐pot synthesis of unsymmetrical diaryl tellurides was developed by the SH2 reaction of in situ generated diphenyl telluride with arylhydrazines in the air. The selectivity of mono‐/di‐substitution and the reactivity of arylhydrazines depend on the nature of the substituents on the arylhydrazines, that is, electron‐donating or ‐withdrawing group.

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Section: Introductionmentioning

confidence: 99%

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Yamamoto

Sato

Kodama

et al. 2018

Heteroatom Chemistry

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“…In order to obtain crystals suitable for X-ray analysis, the halogenation of selenides 7a,b and 8a,b, with bromine and sulfuryl chloride, was carried out. We found that the halogenation reaction Stereoselectivity of the addition of selenium halides to unsaturated compounds has been basically studied for acetylenes [45,[50][51][52][53][54][55][56]. The reactions of selenium dichloride and dibromide with acetylene occurred stereoselectively as anti-addition affording (E,E)-bis(2-halovinyl) selenides in high yields [50].…”

Section: Resultsmentioning

confidence: 99%

“…Efficient electrophilic selenium-containing reagents, selenium dichloride and dibromide, were first introduced in synthesis of organoselenium compounds in 2003 [15,16]. It has been demonstrated that selenium dichloride [17] and dibromide [15] (generated in situ from elemental selenium and sulfuryl chloride or bromine) can be successfully used for selective introduction of the selenium atom Stereoselectivity of the addition of selenium halides to unsaturated compounds has been basically studied for acetylenes [45,[50][51][52][53][54][55][56]. The reactions of selenium dichloride and dibromide with acetylene occurred stereoselectively as anti-addition affording (E,E)-bis(2-halovinyl) selenides in high yields [50].…”

Section: Introductionmentioning

confidence: 99%

Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes

et al. 2020

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The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts of selenium dibromide with alkenes or cycloalkenes easily exchange SeBr2 with other unsaturated compounds, including acetylenes, at room temperature, in acetonitrile. Similar alkene-to-alkene and alkene-to-alkyne transfer reactions of the PhSeBr adducts with alkenes or cycloalkenes take place. The supposed reaction pathway includes the selenium group transfer from seleniranium species to alkenes or alkynes. It was found that the efficient SeBr2 and PhSeBr transfer reagents are Se(CH2CH2Br)2 and PhSeCH2CH2Br, which liberate ethylene, leading to a shift in equilibrium. The regioselective and stereoselective synthesis of bis(E-2-bromovinyl) selenides and unsymmetrical E-2-bromovinyl selenides was developed based on the SeBr2 and PhSeBr transfer reactions which proceeded with higher selectivity compared to analogous addition reactions of SeBr2 and PhSeBr to alkynes under the same conditions.

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“…Current applications of organotellurium compounds are shown in antioxidant activities, intermediates catalysts, nanostructures in biology, and biological detection systems such as biosensors . Rational design of the novel tellurodibenzoic acids was applied from several alternatives of organotellurium compounds as the mimics of kidney‐type glutaminase (KGA) inhibitors because of excellent stability under acidic, basic, and oxidative conditions …”

Section: Introductionmentioning

confidence: 99%

Computational modeling of the kinetics and mechanism of tellurium‐based glutathione peroxidase mimic

Kheirabadi

Izadyar

2020

Int J of Quantum Chemistry

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A new generation of glutathione peroxidase enzyme mimic based on organotellurium was introduced. The catalytic cycles of these mimics, tellura and tellenol, were clarified by density functional theory and solvent-assisted proton exchange procedure as an indirect proton exchange chain. From the kinetic viewpoint, the oxidation of tellura (ΔG 6 ¼ = 23.55 kcal mol −1 ) was considered as the rate-determining step using a single-step process. Various behaviors of tellenol were examined in the reduction of tellurenylsulfide based on methanethiol nucleophilicity. On the basis of the turnover frequency calculations, during the catalytic cycles of tellura and tellenol, the rate of the catalytic cycle of tellura is faster than that of tellenol. A decrease in the electron density and an increase in the Laplacian from the reactant to the transition states are evidence of the bond rupture, whereas an opposite change is evidence of the bond formation. Finally, different analyses of the electron location function and localized orbital locator within the quantum theory of atoms in molecules were applied and discussed. The covalent nature of the intramolecular interactions suggests that the TeÁ Á ÁN interaction is stronger than that of TeÁ Á ÁH. Finally, based on different analyses, tellura can be considered the more reactive GPx mimic than tellenol. K E Y W O R D Sglutathione, peroxidase, mimic, tellurium, turnover frequency, GPx mimics

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Stereoselective synthesis of E-2-halovinyl tellanes, ditellanes and selenides based on tellurium tetrahalides, selenium dihalides and internal alkynes

Cited by 16 publications

References 41 publications

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Reaction of arylhydrazines with diaryl ditellurides in the air: Insight into bimolecular homolytic substitution on tellurium via Aryl–Te bond cleavage

Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes

Computational modeling of the kinetics and mechanism of tellurium‐based glutathione peroxidase mimic

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