Mild generation of selenolate nucleophiles by thiol reduction of diselenides: convenient syntheses of selenyl-substituted aryl aldehydes

Dubey, Rajeev K.; Hangeun, Lee; Nam, Do‐Hyun; Lim, Dongwook

doi:10.1016/j.tetlet.2011.10.075

Cited by 16 publications

(12 citation statements)

References 40 publications

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“…The key step was a chemoselective arylation of diselenide 1 . Several methods of nucleophilic aromatic substitution of selenolate anion generated from diselenide [ 15 ] and selenocyanide. It was expected that high nucleophilicity of selenolate anion (RSe – ) would react selectively with an arylating agent in the presence of other functional groups including thiol, amine, carboxylic acid, and alcohol.…”

Section: Methodsmentioning

confidence: 99%

Chemoselective Arylation of Dialkyl Diselenides and Application to the Synthesis of a ε‐N,N,N‐Trimethyllysine Derivative

et al. 2020

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Nucleophilic aromatic substitution of a dialkyl diselenide with 1‐bromo‐2,4‐dinitrobenzene and sodium borohydride in EtOH/THF proceeded chemoselectively in the presence of a thiol, an amine, and a carboxylic acid. ε‐N,N,N‐Trimethyllysine derivative was synthesized from selenohomocysteine dimer by the present arylation, oxidation, cross‐metathesis with 4‐iodobutene, reduction, and substitution with trimethylamine.

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Section: Methodsmentioning

confidence: 99%

Chemoselective Arylation of Dialkyl Diselenides and Application to the Synthesis of a ε‐N,N,N‐Trimethyllysine Derivative

et al. 2020

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“…[40] Synthesis of HemiSe.T oastirred solution of (E)-1,1,3-trimethyl-2-(2-(phenylselanyl)styryl)-1H-benzo[e]indol-3-ium To aw ell-stirred solution of aldehyde (0.090 g, 0.343 mmol) in 10 mL of dry EtOH was added 1,1,2,3-tetramethyl-1H-benzo[e]indolium hexafluorophosphate (0.140 gm, 0.378 mmol) at room temperature. [40] Synthesis of HemiSe.T oastirred solution of (E)-1,1,3-trimethyl-2-(2-(phenylselanyl)styryl)-1H-benzo[e]indol-3-ium To aw ell-stirred solution of aldehyde (0.090 g, 0.343 mmol) in 10 mL of dry EtOH was added 1,1,2,3-tetramethyl-1H-benzo[e]indolium hexafluorophosphate (0.140 gm, 0.378 mmol) at room temperature.…”

Section: Synthesismentioning

confidence: 99%

“…The 2-(phenylseleno)-benzaldehyde, intermediate was synthesized according to ak nown literature. [40] Synthesis of HemiSe.T oastirred solution of (E)-1,1,3-trimethyl-2-(2-(phenylselanyl)styryl)-1H-benzo[e]indol-3-ium To aw ell-stirred solution of aldehyde (0.090 g, 0.343 mmol) in 10 mL of dry EtOH was added 1,1,2,3-tetramethyl-1H-benzo[e]indolium hexafluorophosphate (0.140 gm, 0.378 mmol) at room temperature. The resulting mixture was then stirred at room temperature for 15 min.…”

Section: Synthesismentioning

confidence: 99%

A Hemicyanine‐Embedded Diphenylselenide‐Containing Probe “HemiSe” in which SePh₂ Stays Reduced for Selective Detection of Superoxide in Living Cells

Halle

Lee

Yudhistira

et al. 2018

Chemistry An Asian Journal

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As imple one-step synthesis of fluorescent probe HemiSe has been developed for the detection of superoxide (O 2 C À ). The probe undergoes reaction specificallyw ith O 2 C À when in the presence of other competitive ROS/RNS/metal ions. The diphenylselenide was incorporated to completely quench the fluorescenceo ft he hemicyanine unit through the action of ap hotoinduced electron transfer (PET) photomechanism.H owever,a fter the addition of O 2 C À ,t he latent fluorophore regains its fluorescence owing to the reaction at the C=Cb ond of the hemicyanine with O 2 C À through nucleophilic attack;t he increase in blue emission is due to ar eac-tion of the doubleb ond within HemiSe followed by an increase in fluorescenceq uantum yield (F)u pt o0 .45;t he limit of detection (LOD) is 11.9 nm.Atime-dependent study shows that HemiSe can detect superoxide within 13 min with high sensitivity,h igh selectivity,o ver aw ide pH range, and through confirmation with ax anthine/xanthine oxidase biochemical assay (l em = 439 nm). As tudy in the RAW2 64.7 macrophage living cells also shows that HemiSe is not toxic, cell permeable (experimental log P = 2.11);c onfocali maging resultss how that HemiSe can detect O 2 C À in endogenous and exogeneous systems.[a] Dr.

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“…Chemical applications of diselenides arise mainly from the convenient inclusion of RSe units in both organic and inorganic synthesis by cleavage of the Se–Se bond; this is mostly influenced by the weaker dissociation energy of this bond in comparison with C–Se, H–Se and S–S bonds . Representative members of this family include (SePh) 2 and (CH 3 Se) 2 , which are compounds widely employed in organic reactions and catalysis because of the high yields achieved (>90%) for the inclusion of PhSe – and CH 3 Se – moieties, respectively …”

Section: Introductionmentioning

confidence: 99%

Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH₃C(O)Se₂C(O)CH₃

Castaño

Romano

Salamanca

et al. 2016

J of Physical Organic Chem

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By oxidation of selenoacetic acid, CH3C(O)SeH, we have prepared the hitherto unknown diacetyl diselenide, [CH3C(O)Se]2. Its vibrational properties were studied experimentally, both in neat liquid (Fourier transform infrared spectroscopy and Raman) with the molecule isolated in argon matrix at low temperatures and theoretically using MP2 and B3LYP methods in combination with 6‐31+G(d), 6‐311++G(3df,3dp) or aug‐cc‐pvDZ basis sets. Analysis of Ar matrix spectra reveals a conformational equilibrium in gas phase at room temperature, which was interpreted by considering only two of the three stable rotamers predicted by our three‐dimensional potential energy surface scans. Energetic properties of three minima found theoretically were further studied in terms of donor–acceptor interactions by using natural bond orbital calculations at the same levels of theory. From this, it was possible to rationalize the conformational stability order and molecular structures by means of vicinal hyperconjugative delocalizations involving lone pairs on selenium or oxygen atoms and C=O, C–C or Se–C antibonding orbitals. The photochemistry of the compound in the argon matrix in the range between 200 and 800 nm was also investigated, revealing only one photochemical path to produce ketene, H2C=C=O, methylselane, CH3SeH, and carbonyl selenide, OCSe. Copyright © 2016 John Wiley & Sons, Ltd.

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Mild generation of selenolate nucleophiles by thiol reduction of diselenides: convenient syntheses of selenyl-substituted aryl aldehydes

Cited by 16 publications

References 40 publications

Chemoselective Arylation of Dialkyl Diselenides and Application to the Synthesis of a ε‐N,N,N‐Trimethyllysine Derivative

Chemoselective Arylation of Dialkyl Diselenides and Application to the Synthesis of a ε‐N,N,N‐Trimethyllysine Derivative

A Hemicyanine‐Embedded Diphenylselenide‐Containing Probe “HemiSe” in which SePh₂ Stays Reduced for Selective Detection of Superoxide in Living Cells

Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH₃C(O)Se₂C(O)CH₃

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Mild generation of selenolate nucleophiles by thiol reduction of diselenides: convenient syntheses of selenyl-substituted aryl aldehydes

Cited by 16 publications

References 40 publications

Chemoselective Arylation of Dialkyl Diselenides and Application to the Synthesis of a ε‐N,N,N‐Trimethyllysine Derivative

Chemoselective Arylation of Dialkyl Diselenides and Application to the Synthesis of a ε‐N,N,N‐Trimethyllysine Derivative

A Hemicyanine‐Embedded Diphenylselenide‐Containing Probe “HemiSe” in which SePh2 Stays Reduced for Selective Detection of Superoxide in Living Cells

Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH3C(O)Se2C(O)CH3

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A Hemicyanine‐Embedded Diphenylselenide‐Containing Probe “HemiSe” in which SePh₂ Stays Reduced for Selective Detection of Superoxide in Living Cells

Vibrational spectra, conformational properties and argon matrix photochemistry of diacetyl diselenide, CH₃C(O)Se₂C(O)CH₃