Reactions of sodium selenide with ethynyl and bromoethynyl ketones: Stereo- and regioselective synthesis of functionalized divinyl selenides and 1,3-diselenetanes

Потапов, В. А.; Елохина, В. Н.; Ларина, Л. И.; Yaroshenko, Tatiana I.; Татаринова, А. А.; Амосова, С. В.

doi:10.1016/j.jorganchem.2009.07.023

Cited by 21 publications

(10 citation statements)

References 26 publications

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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%

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(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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Section: Introductionmentioning

confidence: 99%

“…Examples of the synthesis of vinyl selenides bearing electron-withdrawing groups are scarce in the literature. The synthesis of ( Z,Z )-bis(2-acylvinyl) selenides by the addition reaction of sodium selenide with organyl ethynyl ketones was developed [ 23 ].…”

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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“…Z , Z -bis(acylvinyl) selenides were exclusively obtained in moderate yields by the reaction of sodium selenide with ethynyl ketones derived from aromatic ketones. Only four examples were prepared and when bromoethynyl ketones were used, 1,3-diselenetanes were obtained instead of the respective divinyl selenides [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol

et al. 2017

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A simple and efficient protocol to prepare divinyl selenides has been developed by the regio- and stereoselective addition of sodium selenide species to aryl alkynes. The nucleophilic species was generates in situ, from the reaction of elemental selenium with NaBH4, utilizing PEG-400 as the solvent. Several divinyl selenides were obtained in moderate to excellent yields with selectivity for the (Z,Z)-isomer by a one-step procedure that was carried out at 60 °C in short reaction times. The methodology was extended to tellurium, giving the desired divinyl tellurides in good yields. Furthermore, the Fe-catalyzed cross-coupling reaction of bis(3,5-dimethoxystyryl) selenide 3f with (4-methoxyphenyl)magnesium bromide 5 afforded resveratrol trimethyl ether 6 in 57% yield.

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“…[1][2][3][4][5][6][7][8][9][10] Besides, organoselenium and organotellurium compounds have attracted increased interest because of their unique biological and pharmacological properties. 11,12 In this way, various methods are mentioned for the preparation of vinyl chalcogenides and the most common protocols involve the addition of organo chalcogenol, or the respective chalcogenolate anions, to terminal or internal alkynes.…”

Section: Introductionmentioning

confidence: 99%

“…11,12 In this way, various methods are mentioned for the preparation of vinyl chalcogenides and the most common protocols involve the addition of organo chalcogenol, or the respective chalcogenolate anions, to terminal or internal alkynes. [1][2][3][4][5][6][7][8][9][10][13][14][15][16][17][18][19][20] On the other hand, ionic liquids (ILs) are receiving much attention in organic synthesis, both as recyclable solvents and/or catalysts. [21][22][23][24][25][26][27][28][29][30][31][32] Because product isolation or catalyst recycling is very easy in ILs and, in some cases, rate accelerations and/or selectivity improvements are also observed, they are regarded as environmentally friendly green solvents.…”

Section: Introductionmentioning

confidence: 99%

NaBH4/[bmim]BF4: a new reducing system to access vinyl selenides and tellurides

Lenardão

Gonçalves

Mendes

et al. 2010

J. Braz. Chem. Soc.

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Um método simples e geral foi desenvolvido para a síntese de selenetos e teluretos vinílicos a partir de alquinos terminais e dicalcogenetos de diorganoíla usando NaBH 4 e [bmim]BF 4 como solvente reciclável. Este método eficiente permite a formação preferencial de calcogenetos vinílicos de configuração Z na maioria dos exemplos estudados. Também foi observado que na reação envolvendo fenilacetileno, (E)-bis-fenilcalcogenoestirenos foram obtidos com bons rendimentos e alta seletividade. O líquido iônico foi reutilizado três vezes sem perda da eficiência.A general and simple method for the synthesis of vinyl selenides and tellurides starting from terminal alkynes and diorganyl chalcogenides using NaBH 4 and [bmim]BF 4 as a recyclable solvent was developed. This efficient and improved method furnishes the corresponding vinyl chalcogenides preferentially with Z configuration. We also observed that when the same protocol was applied to phenyl acetylene, (E)-bis-phenylchalcogeno styrenes were obtained in good yields and high selectivity. The ionic liquid was reused up three times without lost of efficiency.

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Reactions of sodium selenide with ethynyl and bromoethynyl ketones: Stereo- and regioselective synthesis of functionalized divinyl selenides and 1,3-diselenetanes

Cited by 21 publications

References 26 publications

(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

(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

Green Hydroselenation of Aryl Alkynes: Divinyl Selenides as a Precursor of Resveratrol

NaBH4/[bmim]BF4: a new reducing system to access vinyl selenides and tellurides

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