Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

Palomba, Martina; Dias, Italo Franco Coelho; Rosati, Ornelio; Marini, Francesca

doi:10.3390/molecules26113148

Cited by 12 publications

(7 citation statements)

References 64 publications

(83 reference statements)

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“…Vinyl selenides are close precursors of vinyl selenones 108 , which are versatile building blocks, especially in C-C bond-forming reactions, due to their double electrophilic nature [ 157 ]. In 2018, Marini et al developed an Oxone-based oxidation method to perform the synthesis of these scaffolds in water [ 158 ].…”

Section: Organoselenium Chemistry In Non-conventional Solventsmentioning

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: Organoselenium Chemistry In Non-conventional Solventsmentioning

confidence: 99%

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

et al. 2022

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“…For this purpose, we synthetically diversified a set of three representative synthesized compounds, such as 5 a, 5 l, and 5 n, to selonones by facile and controlled oxidation by m-chloroperbenzoic acid (m-CPBA) to produce selenoxides 15 (Scheme 5) in good yields, following the standard procedure. [15] Selenones are interesting organoselenium compounds that find immense application as building blocks for a handful of natural and synthetic bioactive molecules [16] and exhibit numerous biological activities. [17]…”

Section: Resultsmentioning

confidence: 99%

Mechanochemical Solvent‐Free One‐Pot Synthesis of Poly‐Functionalized 5‐(Arylselanyl)‐1H‐1,2,3‐triazoles Through a Copper(I)‐Catalyzed Click Reaction

Karmakar,

Mukherjee

et al. 2023

Chemistry A European J

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A mechanochemistry‐driven practical and efficient synthetic protocol for accessing diverse series of biologically relevant poly‐functionalized 5‐(arylselanyl)‐1H‐1,2,3‐triazoles through copper(I)‐catalyzed click reaction between aryl/heteroaryl acetylenes, diaryl diselenides, benzyl bromides, and sodium azide has been accomplished under high‐speed ball‐milling. Advantages of this method include operational simplicity, avoidance of using solvent and external heating, one‐pot synthesis, short reaction time in minutes, good to excellent yields, broad substrate scope, and gram‐scale applications. Furthermore, synthesized organoselenium compounds were synthetically diversified to biologically promising selenones.

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“…Organochalcogen compounds are widely used as functional materials and pharmaceuticals [ 1 , 2 ]. These functional molecules are mainly synthesized using ionic and metal-assisted reactions [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

et al. 2021

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In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy•). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.

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Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

Cited by 12 publications

References 64 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

Mechanochemical Solvent‐Free One‐Pot Synthesis of Poly‐Functionalized 5‐(Arylselanyl)‐1H‐1,2,3‐triazoles Through a Copper(I)‐Catalyzed Click Reaction

Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light

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