Electrophilic Selenium

Santi, Claudio; Santoro, Stefano

doi:10.1002/9783527641949.ch1

Cited by 31 publications

(30 citation statements)

References 201 publications

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“…Considering their usage in organic synthesis diselenides possess several advantages -they are stable and can be easily converted to electrophilic, nucleophilic and radical reagents. [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] The biological potential of diaryl diselenides is mainly associated with their GPx-like activity. Glutathione peroxidase (GPx) is a selenoenzyme that, based on the presence of catalytically active aminoacid selenocysteine (Sec, U), eliminates reactive oxygen and nitrogen species enabling to maintain the redox homeostasis inside the cell.…”

Section: Introductionmentioning

confidence: 99%

Water-dependent synthesis of biologically active diaryl diselenides

Pacuła¹,

Obieziurska²,

Ścianowski³

et al. 2018

Arkivoc

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A new one-step method for the synthesis of diaryl diselenides has been developed. The reaction of oiodobenzamides with dilithium diselenide can be controlled by the presence of water providing a simple and efficient protocol to obtain benzisoselenazolones or diaryl diselenides. A series of N-aryl ebselen derivatives and the corresponding diselenides was obtained. All synthesized compounds were tested in vitro as antioxidants and cytotoxic agents. N- (2,3,4-trimethoxyphenyl)benzisoselenazol-3(2H)-one was the best in vitro antioxidant and the corresponding diselenide the most potent cytotoxic agent against prostate cancer cell line DU145, being inactive towards healthy prostate cell line PNT1A.

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Section: Introductionmentioning

confidence: 99%

Water-dependent synthesis of biologically active diaryl diselenides

Pacuła¹,

Obieziurska²,

Ścianowski³

et al. 2018

Arkivoc

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“…The interaction between a cationic ChR + (Ch = S or Se) moiety and an unsaturated CC bond has been studied since 1950s, 1,2 when the addition of PhChCl to polar and nonpolar alkenes was discovered. Such Lewis acids (LAs), called thiiranium and seleniranium ions, are important intermediates in many chemical processes 3−5 and have been isolated and characterized by NMR spectroscopy 6−8 and, in some cases, by X-ray diffractometry.…”

Section: Introductionmentioning

confidence: 99%

“…In particular, the Se ← olefin σ donation makes the olefin electron-poor and suitable for a nucleophilic attack. 1 It has been recently observed that the presence of a Lewis base (LB), generally soft and in many cases containing another chalcogen as, for example, R 3 PCh (Ch = oxygen, sulfur or selenium), strongly increases the rate and the yield of the nucleophilic attack (LB activation of LA, LBLA). 20,21 Even more importantly, if the LB is chiral it can induce excellent stereoselectivity to the entire process.…”

Section: Introductionmentioning

confidence: 99%

Lewis Base Activation of Lewis Acid: A Detailed Bond Analysis

Ciancaleoni

2018

ACS Omega

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The effect of a Lewis base (LB) on the nucleophilic attack on chalcogeniranium (chalcogen = sulfur and selenium) cations, the so-called LB activation of a Lewis acid, has been studied coupling natural orbital for chemical valence decomposition of the orbital interaction energy with charge displacement analysis. This methodology provides a detailed and accurate description of all the interactions (LB···chalcogen, chalcogen···olefin and olefin···ammonia) present in the system and leads to a deeper understanding of how they influence each other at all stages of the reaction: reactant complex, transition state, and product complex. In particular, the bond between the chalcogen and the olefin has been decomposed in terms of σ donation/π back-donation and the bond components quantified. This allowed determination of a linear relationship between the activation barrier of the nucleophilic attack and the net amount of charge donated by the olefin to the chalcogen.

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“…These derivatives can be easily transformed into nucleophilic, electrophilic and radical reagents providing highly efficient precursors for new bond formation. [3][4][5][6][7][8] Looking for new selenium derivatives is also interesting due to their biological and pharmacological functions. [9][10][11][12][13][14][15] Addition to double bonds is one of the most common chemical transformations.…”

Section: Introductionmentioning

confidence: 99%

Reactivity of dipinanyl diselenides functionalized at C-10-position with -CH2O(Se)Ph, -OH and -OCPh3 substituents

Ścianowski¹,

Szumera²,

Pacuła³

et al. 2016

Arkivoc

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Terpenyl alcohols, (-)-nopol and (-)-myrtenol were efficiently applied in the synthesis of new diselenides. The pinane skeleton, as the core of the structure, was decorated at the C-10 position by hydroxyl and O-trityl groups, and also OPh and SePh substituents connected to the C-10 carbon by -CH 2 -linker. The diselenides were transformed to electrophilic selenium reagents and tested in asymmetric methoxyselenenylation of styrene, and selenocyclization of o-allylphenol.

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Electrophilic Selenium

Cited by 31 publications

References 201 publications

Water-dependent synthesis of biologically active diaryl diselenides

Water-dependent synthesis of biologically active diaryl diselenides

Lewis Base Activation of Lewis Acid: A Detailed Bond Analysis

Reactivity of dipinanyl diselenides functionalized at C-10-position with -CH2O(Se)Ph, -OH and -OCPh3 substituents

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