Synthesis of vinyl selenides and tellurides using PEG-400

Lenardão, Eder J.; Silva, Márcio S.; Sachini, Maraísa; Lara, Renata G.; Jacob, Raquel G.; Perin, Gelson

doi:10.3998/ark.5550190.0010.b19

Cited by 41 publications

(8 citation statements)

References 2 publications

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“…PEG-400 and glycerol were similarly employed as recyclable solvents for hydrochalcogenation reactions of phenylacetylene (Scheme 22). 54 The nucleophilic species of selenium and tellurium were in this case generated in situ from the corresponding diphenyl dichalcogenide and NaBH alkenes 32 was observed when glycerol was used as solvent. The lower solubility of the starting materials in glycerol vs. PEG-400 was evoked to explain the different reactivities observed.…”

Section: Organic Synthesis Without Transition Metalsmentioning

confidence: 94%

Glycerol and derived solvents: new sustainable reaction media for organic synthesis

et al. 2011

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The rapid growth of the biodiesel industry has led to a large surplus of its major byproduct, i.e. glycerol, for which new applications need to be found. Research efforts in this area have focused mainly on the development of processes for converting glycerol into value-added chemicals and its reforming for hydrogen production, but recently, in line with the increasing interest in the use of alternative greener solvents, an innovative way to revalorize glycerol and some of its derivatives has seen the light, i.e. their use as environmentally friendly reaction media for synthetic organic chemistry. The aim of the present Feature Article is to provide a comprehensive overview on the developments reached in this field.

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Section: Organic Synthesis Without Transition Metalsmentioning

confidence: 94%

Glycerol and derived solvents: new sustainable reaction media for organic synthesis

et al. 2011

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“…With the rising applications of vinyl chalcogenides as pharmaceuticals, functional materials or synthetic reagents, economic and selective methods for their production became an inevitable requirement 1–5 . Two common approaches for the synthesis of these target compounds are cross coupling and addition reactions.…”

Section: Introductionmentioning

confidence: 99%

Computationally unraveling the mechanism and selectivity of five and six membered N‐heterocyclic carbene‐catalyzed alkyne hydrochalcogenation

Jayasree

Reshma

Aswathy

2021

Int J of Quantum Chemistry

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The present work is intended to bring to the forefront a relatively less explored area of N-Heterocyclic Carbene (NHC) catalyzed alkyne hydro-thiolation and selenation reactions by exploring the reaction mechanism. Reaction mechanism involves chalcogenol activation followed by alkyne insertion and the second step is the rate determining step. A comparison with the reported uncatalyzed gas phase reaction showed that a simple imidazol-2-ylidene catalyst can lower the free energy barrier by 28.74 and 21.73 kcal/mol respectively for acetylene hydro-thiolation and selenation reaction. All the employed NHCs are proved to be better catalyst for both hydrothiolation and hydroselenation. Factors such as changing the heterocycle, increasing the conjugation, ring expansion and electronic/steric substitution at the heteroatom were found to affect the energy barriers due to the geometric variations at NHCcarbon and S/Se in the intermediate and the transition structure corresponding to alkyne insertion. Effect of solvent polarity on the reaction energetics and selectivity has also been analyzed employing THF, DMSO and MeOH as the solvents.

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“…The main methods for the preparation of vinyl selenides include a transition metal catalyzed coupling of vinyl halides with diselenides or selenols [ 13 , 14 , 15 , 16 ], reactions of thiols or chalcogenolates with selenoalkynes [ 14 , 17 , 18 ], and addition of selenium-centered nucleophiles to acetylenes [ 8 , 14 , 19 , 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

“…One of the most useful and atom-economic methods is based on addition reactions of selenoles or selenolate anions with acetylenes [ 8 , 14 , 19 , 20 , 21 , 22 ]. Examples of these reactions refer mainly to vinyl selenides containing aliphatic or aromatic substituents at the β-carbon atom of the double bond.…”

Section: Introductionmentioning

confidence: 99%

(Z,Z)-Selanediylbis(2-propenamides): Novel Class of Organoselenium Compounds with High Glutathione Peroxidase-Like Activity. Regio- and Stereoselective Reaction of Sodium Selenide with 3-Trimethylsilyl-2-propynamides

et al. 2020

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The efficient regio- and stereoselective synthesis of (Z,Z)-3,3′-selanediylbis(2-propenamides) in 76–93% yields was developed based on the reaction of sodium selenide with 3-trimethylsilyl-2-propynamides. (Z,Z)-3,3′-Selanediylbis(2-propenamides) are a novel class of organoselenium compounds. To date, not a single representative of 3,3′-selanediylbis(2-propenamides) has been described in the literature. Studying glutathione peroxidase-like properties by a model reaction showed that the activity of the obtained products significantly varies depending on the organic moieties in the amide group. Divinyl selenide, which contains two lipophilic cyclohexyl substituents in the amide group, exhibits very high glutathione peroxidase-like activity and this compound is considerably superior to other products in this respect.

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Synthesis of vinyl selenides and tellurides using PEG-400

Cited by 41 publications

References 2 publications

Glycerol and derived solvents: new sustainable reaction media for organic synthesis

Glycerol and derived solvents: new sustainable reaction media for organic synthesis

Computationally unraveling the mechanism and selectivity of five and six membered N‐heterocyclic carbene‐catalyzed alkyne hydrochalcogenation

(Z,Z)-Selanediylbis(2-propenamides): Novel Class of Organoselenium Compounds with High Glutathione Peroxidase-Like Activity. Regio- and Stereoselective Reaction of Sodium Selenide with 3-Trimethylsilyl-2-propynamides

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