Oxidation of Alkynes in Aqueous Media Catalyzed by Diphenyl Diselenide

Santoro, Stefano; Battistelli, Benedetta; Gjoka, Blerina; Steven, Chun-wing; Testaferri, Lorenzo; Tiecco, Marcello; Santi, Claudio

doi:10.1055/s-0029-1219817

Cited by 14 publications

(4 citation statements)

References 7 publications

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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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Section: Diphenyl Diselenidementioning

confidence: 99%

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

Tiezza¹,

Ribaudo

Orian³

2019

COC

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“…1 In the past two decades, several authors have thoroughly studied the applications of diphenyl diselenides in organic catalysis, as reported by Wirth. [2][3][4][5][6] Santi and co-workers investigated their use in green chemistry [7][8][9][10][11] and pharmaceutical applications. [12][13][14][15][16] The chemical interest is mainly due to the catalytic properties of diphenyl diselenides, which are largely used in important classes of organic reactions, like Baeyer-Villiger oxidations of aldehydes and ketones, oxidations of alcohols and nitrogen containing compounds and alkene epoxidations.…”

Section: Introductionmentioning

confidence: 99%

Thiol modifier effects of diphenyl diselenides: insight from experiment and DFT calculations

et al. 2023

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“…However, the obtained selanyl halides are unstable and difficult to prepare (Santi, 2014). Due to the disadvantages of the use of halogenated selenium species, new alternatives have been described in the literature for the generation of electrophilic selenium species, such as the use of inorganic salts such as sodium (Kibriya et al, 2017), potassium (Santi & Tidei, 2014;Prasad et al, 2013) and ammonium (Tiecco et al, 1989;Santi et al, 2008;Santoro et al, 2010) persulfate through the in situ reaction with diorganyl diselenides. Naphthalenes and their derivatives are known for their countless biological properties reported in the literature, like anticancer (Norton et al, 2008), antifungal (Iverson & Uetrecht, 2001) and antiviral activities (Yeo et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Peer Review #3 of "Ultrasound-promoted synthesis of 2-organoselanyl-naphthalenes using Oxone® in aqueous medium as an oxidizing agent (v0.1)"

Alotaibi¹

2018

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A green methodology to synthesize 2-organoselanyl-naphthalenes based on the reaction of alkynols with diaryl diselenides is described. The electrophilic species of selenium were generated in situ, by the oxidative cleavage of the Se-Se bond of diaryl diselenides by Oxone ® using water as the solvent. The reactions proceeded efficiently under ultrasonic irradiation as an alternative energy source, using a range of alkynols and diorganyl diselenides as starting materials. Through this methodology, the corresponding 2organoselanyl-naphthalenes were obtained in moderate to good yields (56-94%) and in short reaction times (0.25 to 2.3 h).

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Oxidation of Alkynes in Aqueous Media Catalyzed by Diphenyl Diselenide

Cited by 14 publications

References 7 publications

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

Organodiselenides: Organic Catalysis and Drug Design Learning from Glutathione Peroxidase

Thiol modifier effects of diphenyl diselenides: insight from experiment and DFT calculations

Peer Review #3 of "Ultrasound-promoted synthesis of 2-organoselanyl-naphthalenes using Oxone® in aqueous medium as an oxidizing agent (v0.1)"

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