Ultrasound Assisted Ring-Opening Reaction of Epoxides with 1,2-DiphenylDiselenide

Cheng, Tanyu; Zheng, Xin; Ke, Qiang

doi:10.3184/174751911x13149579868111

Cited by 11 publications

(4 citation statements)

References 30 publications

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“…In 2011, Cheng and co‐workers developed an US‐assisted regioselective ring‐opening reaction of epoxides 64 promoted by Na 2 S 2 O 4 , which was efficient in the generation of nucleophilic selenium species from diphenyl diselenide 60 . The reaction was conducted in the presence of K 2 CO 3 as base, and the respective β ‐hydroxyselenides 66 were obtained in satisfactory yields (Scheme ).…”

Section: Synthesis Of Organochalcogen Compoundsmentioning

confidence: 99%

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

et al. 2018

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In the last two decades, the search for sustainability in chemical reactions has attached a lot of attention. In this focus review, the use of ultrasound (US) as an alternative energy source in organic synthesis is presented. The improvement of the performance of chemical reactions due to the cavitation effect has been previously studied and described. The use of US guarantees often higher yields than other green methodologies, as microwave or ball milling. The impressive positive effect of US in organic synthesis are demonstrated in this review mainly in organometallic and multi-component reactions (MCRs), aimed to prepare bioactive compounds. A particular attention is dedicated to the US-assisted synthesis of valuable organochalcogen compounds with pharmacological activity.[a] F.

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Section: Synthesis Of Organochalcogen Compoundsmentioning

confidence: 99%

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

et al. 2018

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“…An important aspect of the organoselenium chemistry is its unexpected applicability in green protocols; selenocompounds can be used as catalysts or electrophilic, nucleophilic, or radical reagents to perform direct functionalization of organic substrates by circumventing the need for protection–deprotection steps, which can be critical when aiming to create environmentally friendly chemical procedures. − Particularly, the green features of organoselenides’ reactivity are the possibility to use safe, nontoxic, and nonconventional media, like water, − ionic liquids, , glycerol, , or solvent-free conditions; , other advantages are the use of alternative sources of energy, like microwaves, , ultrasounds, − or electrochemistry; and the application in bioinspired catalysis. − …”

Section: Introductionmentioning

confidence: 99%

Role of Group 12 Metals in the Reduction of H₂O₂by Santi’s Reagent: A Computational Mechanistic Investigation

Zeppilli,

Madabeni,

Sancineto

et al. 2023

Inorg. Chem.

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PhSeZnCl, which is also known as Santi’s reagent, can catalyze the reduction of hydrogen peroxide by thiols with a GPx-like mechanism. In this work, the first step of this catalytic cycle, i.e., the reduction of H2O2 by PhSeZnCl, is investigated in silico using state-of-the-art density functional theory calculations. Then, the role of the metal is evaluated by replacing Zn with its group 12 siblings (Cd and Hg). The thermodynamic and kinetic factors favoring Zn are elucidated. Furthermore, the role of the halogen is considered by replacing Cl with Br in all three metal compounds, and this turns out to be negligible. Finally, the overall GPx-like mechanism of PhSeZnCl and PhSeZnBr is discussed by evaluating the energetics of the mechanistic path leading to the disulfide product.

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“…On the other hand, the use of alternative energy sources has become a remarkable factor in organic synthesis, in order to circumvent the use of oil-based energies. In this context, several methods involving the hydroxyselenation of olefins have been using alternative energy sources, including microwave irradiation [17], ultrasonic irradiation [18], and electricity [19].…”

Section: Introductionmentioning

confidence: 99%

Benzeneseleninic Acid in the Photo-Catalyzed Hydroxy-Selenylation of Styrenes

Penteado

Bettanin

Machado

et al. 2020

The 1st International Electronic Conference on Catalysis Sciences

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We established a new visible-light-mediated protocol for the regioselective βhydroxyselenylation of olefins, employing benzeneseleninic acid as substrate. Regarding a novel approach, the benzeneseleninic acid emerges as an efficient and affordable reagent to be used as an electrophilic selenium source that can be easily converted to selenium-based radical species under visible-light conditions. In this sense, the photocatalytically formed PhSe• radical can react directly with unsaturated substrates, including alkenes, to access a new C-Se bond and a carbon-centered radical intermediate, which finally is trapped by a hydroxyl radical species, delivering the βhydroxyselanyl compounds. Thus, despite the versatile utilities in organic synthesis, such as building blocks, the β-hydroxyselanyl compounds have demonstrated important biological activities. Based on that, we concentrated our efforts on developing a robust, effective, and environmentally benign methodology for their preparation. The optimal condition involves the reaction between styrene and 1.0 equivalent of phenylseleninic acid, in the presence of 5.0 mol% of eosin Y, as a cheap and easily available photocatalyst, with DMSO promoting the reaction medium. Satisfactorily, the system was irradiated with blue LED light for 2 h, to deliver the desired products in good yields.

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Ultrasound Assisted Ring-Opening Reaction of Epoxides with 1,2-DiphenylDiselenide

Cited by 11 publications

References 30 publications

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

Role of Group 12 Metals in the Reduction of H₂O₂by Santi’s Reagent: A Computational Mechanistic Investigation

Benzeneseleninic Acid in the Photo-Catalyzed Hydroxy-Selenylation of Styrenes

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Ultrasound Assisted Ring-Opening Reaction of Epoxides with 1,2-DiphenylDiselenide

Cited by 11 publications

References 30 publications

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

Ultrasound‐Assisted Multicomponent Reactions, Organometallic and Organochalcogen Chemistry

Role of Group 12 Metals in the Reduction of H2O2by Santi’s Reagent: A Computational Mechanistic Investigation

Benzeneseleninic Acid in the Photo-Catalyzed Hydroxy-Selenylation of Styrenes

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Role of Group 12 Metals in the Reduction of H₂O₂by Santi’s Reagent: A Computational Mechanistic Investigation