Electrochemical selenation of phosphonates and phosphine oxides

Guo, Shengmei; Li, Sen; Zhang, Zhebin; Yan, Wenjie; Cai, Hu

doi:10.1016/j.tetlet.2019.151566

Cited by 15 publications

(8 citation statements)

References 38 publications

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“…The development of this type of protocol Organoselenophosphorus derivatives have been gaining attention due to application in several areas [56]. Among the methodologies developed for the synthesis of this type of molecule, the electrocatalytic-mediated selenylation of phosphonates or phosphine oxides 57, by Cai et al [57], is highlighted (Scheme 27). The ecofriendly protocol was conducted during 6 h under air and employed a platinum anode and a platinum cathode with constant current, nBu 4 NBr and acetonitrile.…”

Section: Photochemistrymentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

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Organoselenium compounds have been successfully applied in biological, medicinal and material sciences, as well as a powerful tool for modern organic synthesis, attracting the attention of the scientific community. This great success is mainly due to the breaking of paradigm demonstrated by innumerous works, that the selenium compounds were toxic and would have a potential impact on the environment. In this update review, we highlight the relevance of these compounds in several fields of research as well as the possibility to synthesize them through more environmentally sustainable methodologies, involving catalytic processes, flow chemistry, electrosynthesis, as well as by the use of alternative energy sources, including mechanochemical, photochemistry, sonochemical and microwave irradiation.

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Section: Photochemistrymentioning

confidence: 99%

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

et al. 2022

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“…Like many selenium‐containing molecules, organoselenophosphorus are relevant compounds from the pharmacological point of view [507,508] . In this sense, a straightforward and efficient electrocatalytic‐mediated selenation of phosphates and phosphine oxides has been recently published [509] . This transformation proceeded in the absence of transition metals, bases and oxidizing agents at room temperature resulting in selenophosphorus products of formula 710 in good to excellent yields as shown in Scheme 150 [509] .…”

Section: Alkyl Selenium Derivativesmentioning

confidence: 99%

“…On the other hand, bromide ion is oxidized to give a molecule of bromine, which reacts with the phosphonate substrate 711 to yield the phosphorobromidate E , which by nucleophilic attack from D gives rise to the title compound (Scheme 150). [509] …”

Section: Alkyl Selenium Derivativesmentioning

confidence: 99%

“…[507,508] In this sense, a straightforward and efficient electrocatalytic-mediated selenation of phosphates and phosphine oxides has been recently published. [509] This transformation proceeded in the absence of transition metals, bases and oxidizing agents at room temperature resulting in selenophosphorus products of formula 710 in good to excellent yields as shown in Scheme 150. [509] The optimal reaction conditions turn out to be a constant current of 12.0 mA, the phosphorus-containing substrate, in which the phosphorusÀ hydrogen bond changes to a phosphorusÀ selenium bond, tetrabutylammonium bromide as electrolyte, acetonitrile as a solvent under air atmosphere and working at room temperature for 6 h.…”

Section: Chalcogenophosphate In Organic Moleculesmentioning

confidence: 99%

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Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium‐containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article, we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium‐containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

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“…Heteroatom bond to phosphorus moieties with selenium is important chemical construction in organic chemistry because Se−P bond could provide some bioactive molecules. An interesting protocol was reported by Cai and co‐workers [56] for the electrochemical formation of Se−P bond. The reaction proceeds between selenols 55 derivatives and phosphonates or phosphines oxides 54 using n‐ Bu 4 NBr as the redox mediator (scheme 37).…”

Section: Electrochemically Induced Phosphorylation Reactionsmentioning

confidence: 99%

Electrochemical Phosphorylation of Organic Molecules

Sbei

Martins

Shirinfar

et al. 2020

The Chemical Record

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Organophosphorus chemistry is a broad field with multi-dimensional applications in research area of organic, biology, drug design and agrochemicals. Conventional methods have been adopted extensively to access phosphorylated compounds that rely on the use of toxic, moisture sensitive phosphorylating agents and occur in the presence of oxidants, catalysts, as well as high temperatures and harsh conditions are required for complete transformations. However, recent progress has been made for phosphorylation reactions using electricity to introduce green and sustainable synthetic procedures. These reactions can be performed at mild conditions and proceed with excellent atom economy. Herein, we targeted electrochemical phosphorylation reactions with generation of new bonds such as C(sp 3) À P, C(sp 2) À P, OÀ P, NÀ P, SÀ P and SeÀ P. This review is aimed to offer an overview of recent developments in the synthetic methodology to easy access of organophosphorus compounds using electrochemistry.

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Electrochemical selenation of phosphonates and phosphine oxides

Cited by 15 publications

References 38 publications

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

“Green Is the Color”: An Update on Ecofriendly Aspects of Organoselenium Chemistry

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Electrochemical Phosphorylation of Organic Molecules

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