DES as a green solvent to prepare 1,2-bis-organylseleno alkenes. Scope and limitations

Lopes, Eliana Franco; Gonçalves, Lóren C.C.; Vinueza, Julio César; Jacob, Raquel G.; Perin, Gelson; Santi, Claudio; Lenardão, Eder J.

doi:10.1016/j.tetlet.2015.10.095

Cited by 21 publications

(12 citation statements)

References 39 publications

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“…Diphenyl selenide 1099 reacted with 1,4-diphenyl-1,3-diyne 1a or hexa-2,4-diyne-1,6-diol 1045 in the presence of NaBH 4 212 in a choline chloride/urea (1/2) mixture at 90 1C to give corresponding (Z)-selenoenynes 1100g and 1130 with excellent selectivity and high yields (Scheme 209a). 441 A similar strategy based on the application of green solvents was used by Lara et al who applied a poly(ethylene glycol) (PEG 400) as an alternative for DES. Depending on the reaction temperature, the (Z)-selenoenynes 1100g-h and 1132a-b or (Z,Z)-1,4-bisselenobuta-1,3dienes 1133a-c were obtained in the reaction of diorganodiselenides 1099, 1112c, and 1131 with the symmetrical 1,3-diynes 1a, 1045, 1072a in the presence of NaBH 4 212.…”

Section: Hydroselenation Of 13-diynesmentioning

confidence: 99%

Hydroelementation of diynes

et al. 2022

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Section: Hydroselenation Of 13-diynesmentioning

confidence: 99%

Hydroelementation of diynes

et al. 2022

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“…The classical protocols for 1,2-bis-organylselanyl alkene synthesis that involves reaction between alkyne 304 and diorganoyl diselenide 4 (Scheme 99) [171][172][173][174][175][176][177][178] is depicted the most representative methodologies for synthesis of 1,2-bis-organylselanyl alkenes 305-310. The stereoselective synthesis of (E)-1,2-bis-arylselanyl alkenes 305-308 includes: (i) use of deep eutethic solvents to carry the reaction in the presence of sodium borohydride: [171] (ii) CuI/Zn/glycerol as a recyclable catalytic system; [172] (iii) microwave reaction using KF/ Al 2 O 3 or NaBH 4 in PEG-400 yielding also the 1arylselanylalkyne as byproduct [173][174] and (iv) by using CFL 25 W at room temperature in DCM solvent. [175] The (Z)-1,2-bisarylselanyl alkenes 309-310 are prepared (v) with palladium catalysis and trialkylphosphite ligands in degassed toluene at 100°C (dinuclear and mononuclear trans palladium-arylchalcogen intermediate complexes were isolated), [176] and (vi) through cesium selenolate nucleophiles [177][178] generated from diaryl diselenides 4 and cesium salts or hydroxide and subsequent addition to terminal alkynes 304.…”

Section: Synthesis Of Bis-and Tris-selenide Alkenementioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

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“…Diphenyl diselenide is a stable compound, currently employed in organic synthesis as catalyst. In combined experimental and theoretical studies, Back and Wirth have extensively explored its catalytic properties and those of its derivatives in numerous reactions [20,[25][26][27][28][29][30][31][32][33][34], while Santi and co-workers have mainly focused on the eco-friendly aspects of the use of diphenyl diselenide in green organic and medicinal chemistry [19][20][21][22][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50].…”

Section: Diphenyl Diselenidementioning

confidence: 99%

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

Tiezza¹,

Ribaudo

Orian³

2019

COC

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Organodiselenides are an important class of compounds characterized by the presence of two adjacent covalently bonded selenium nuclei. Among them, diaryldiselenides and their parent compound diphenyl diselenide attract continuing interest in chemistry as well as in close disciplines like medicinal chemistry, pharmacology and biochemistry. A search in SCOPUS database has revealed that in the last three years 105 papers have been published on the archetypal diphenyl diselenide and its use in organic catalysis and drug tests. The reactivity of the Se-Se bond and the redox properties of selenium make diselenides efficient catalysts for numerous organic reactions, such as Bayer- Villiger oxidations of aldehydes/ketones, epoxidations of alkenes, oxidations of alcohols and nitrogen containing compounds. In addition, organodiselenides might find application as mimics of glutathione peroxidase (GPx), a family of enzymes, which, besides performing other functions, regulate the peroxide tone in the cells and control the oxidative stress level. In this review, the essential synthetic and reactivity aspects of organoselenides are collected and rationalized using the results of accurate computational studies, which have been carried out mainly in the last two decades. The results obtained in silico provide a clear explanation of the anti-oxidant activity of organodiselenides and more in general of their ability to reduce hydroperoxides. At the same time, they are useful to gain insight into some aspects of the enzymatic activity of the GPx, inspiring novel elements for rational catalyst and drug design.

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DES as a green solvent to prepare 1,2-bis-organylseleno alkenes. Scope and limitations

Cited by 21 publications

References 39 publications

Hydroelementation of diynes

Hydroelementation of diynes

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

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