Convenient synthesis of new Se,Se′-disubstituted derivatives of benzene-1,2-diselenol

Meunier, Philippe; Gautheron, B.; Mazouz, Ahmed

doi:10.1039/c39860000424

Cited by 24 publications

(6 citation statements)

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“…Notably, the reactivity of the complex 47 with other electrophiles was also exploited to access differently Se,Se'-disubstituted derivatives, including selenides and selenolesters (Scheme 23). [66] Kimura and co-workers reported the preparation of the benzenediselenol 35 m from the corresponding cyanoethyl selenide 52 through the CsOH-promoted cleavage of the CÀ Se bond, followed by treatment with HCl. Bis(aryl-alkyl)selenide 52 could be efficiently achieved by reduction and alkylation of the benzotriselenole 51 (Scheme 24).…”

Section: Other Methodologies For the Synthesis Of Aromatic Selenolsmentioning

confidence: 99%

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Synthesis and Applications of Organic Selenols

Tanini

Capperucci

2021

Adv Synth Catal

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The synthesis and the study of organoselenium compounds have received much attention over the past decades. Selenium-containing organic molecules are widely used in organic synthesis, materials science, and medicinal chemistry. Selenium -and more specifically the amino acid selenocysteine, bearing a selenol (SeH) moiety -is present in at least 25 human protein families, whose biological functions have not been completely identified. Amongst the variety of organoselenium compounds, selenols are a versatile class of molecules easily undergoing a broad array of useful transformations. Because of the unique properties of the SeH group, selenol chemistry has important applications in chemical sciences, spanning from organic synthesis to materials chemistry and biology. This review summarises currently available methodologies for the synthesis of selenols and highlights applications of selenols in chemical sciences and biology. Conclusions and Outlook 5.1. Safety Measures

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Section: Other Methodologies For the Synthesis Of Aromatic Selenolsmentioning

confidence: 99%

“…Notably, the reactivity of the complex 47 with other electrophiles was also exploited to access differently Se,Se’‐disubstituted derivatives, including selenides and selenolesters (Scheme 23). [66] …”

Section: Synthesis Of Selenolsmentioning

confidence: 99%

Synthesis and Applications of Organic Selenols

Tanini

Capperucci

2021

Adv Synth Catal

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“…After 100% conversion of 2,6-di-tert-butylphenol the initial Table 1. Autoxidation of 2,6-di-tert-butylphenol catalyzed by anionic cobalt(II) porphyrin complexes (1)(2)(3)(4)(5) amount of the phenol was fed into the reaction mixture without separation of the reaction products. Deactivation of catalyst L-1 was observed after the second run, the recycled catalyst was found to be 0.2 times as active as the fresh catalyst.…”

Section: Catalysts Reusementioning

confidence: 99%

“…Oxidation reactions catalyzed by metalloporphyrins have attracted attention in relevance to the activation of molecular oxygen and oxygen atom transfer to organic substrates, which are processes dependent on cytochrome P-450 in biological systems [1,2]. The utility of these catalysts, would be increased significantly if they could be attached to solid supports, since this should stabilize the catalysts [3] and aid their recovery and reuse [4].…”

Section: Introductionmentioning

confidence: 99%

Studies on the oxidation of 2,6-di-tert-butylphenol by molecular oxygen catalyzed by cobalt(II) tetraarylporphyrins bound to cationic latex

Hassanein

Gerges

Abdo

et al. 2005

J. Porphyrins Phthalocyanines

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A cationic latex has been prepared by emulsion copolymerization of styrene and divinylbenzene with 2 mol.% of quaternary ammonium ion surfactant monomer. The catalytic activity of cobalt(II) sulfonated tetraarylporphrins 1-5 supported on the cationic latex 6 was investigated in the autoxidation of 2,6-di-tert-butylphenol in water. All colloidal catalysts showed good catalytic activity in the autoxidation of 2,6-di-tert-butylphenol. Reaction products were identified as 2,6-ditert-butyl-1,4-benzoquinone and the oxidative coupling product as 3,3ʼ,5,5ʼ-tetra-tert-butyl-4,4ʼ-diphenoquinone. The rate of autoxidation reaction catalyzed by 5 supported on cationic latex was found to increase with increasing pH in the range 7.0-10.0. At constant concentration of cobalt(II) porphyrin 5 in the reaction mixture, the rate as a function of the weight of the latex showed a maximum. The rate of autoxidation increased with increasing partial pressure of dioxygen in the range between 0.2 and 1.0 atm. 5,10,15,20-tetrakis(2,4,6-trimethyl-3,5-disulfonatopheny)porphyrinatocobalt(II) bound to the cationic latex was found to be the most reactive catalyst and the latex supported 5,10,15,20-tetrakis(2,6-dichloro-3-sulfonatophenyl)porphyrinatocobalt(II) showed the highest stability.

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“…Traditional synthetic routes for aryl chalcogenides involve the use of chalcogenols, but due to their toxicity, synthetic routes involving dilithium salts are preferentially used nowadays. 13,15 Special interest was focussed on zirconocene dichalcogenides although high temperatures were required for the complex formation. 3,[15][16][17] Access to titanium and hafnium analogues through transmetallation decreased their overall yields dramatically to 40%, 18 and therefore the use of dilithium salts of diselenolate ligands with metallocene dichlorides was a good compromise for simple synthetic design and achieving high yields.…”

Section: Introductionmentioning

confidence: 99%

Macrocycles containing 1,1′-ferrocenyldiselenolato ligands on group 4 metallocenes

et al. 2018

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were prepared and characterized by 77 Se NMR spectroscopy and the crystal structures of 1-3 and 5 were determined by single-crystal X-ray diffraction. The crystal structure of 4 is known and the complex is isomorphous with 5. 1-5 form mutually similar macrocyclic tetranuclear complexes in which the alternating Fe(C 5 H 4 Se) 2 and M(C 5 H 4 R) 2 centers are linked by selenium bridges. The thermogravimetric analysis (TGA) of 1-3 under a helium atmosphere indicated that the complexes undergo a two-step decomposition upon heating. The final products were identified using powder X-ray diffraction as Fe x MSe 2 , indicating their potential as single-source precursors for functional materials.

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Convenient synthesis of new Se,Se′-disubstituted derivatives of benzene-1,2-diselenol

Cited by 24 publications

References 1 publication

Synthesis and Applications of Organic Selenols

Synthesis and Applications of Organic Selenols

Studies on the oxidation of 2,6-di-tert-butylphenol by molecular oxygen catalyzed by cobalt(II) tetraarylporphyrins bound to cationic latex

Macrocycles containing 1,1′-ferrocenyldiselenolato ligands on group 4 metallocenes

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