Visible‐Light‐Induced Difunctionalization of Styrenes: An Efficient and Green Protocol for the Synthesis of β‐Acyloxyselenides

Chen, Jinyang; Chen, Rui; Mei, Lan; Yan, Shan-Shu; Wu, Yan; Li, Qiang; Yuan, Binfang

doi:10.1002/ajoc.201900676

Cited by 14 publications

(13 citation statements)

References 78 publications

(11 reference statements)

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“…All these advantages have meant that in the last seven years there has been a significant increase in the number of works reporting the use of photochemistry in the seleno-functionalization of several classes of organic substrates [ 70 ]. For example, the carbon-selenium bond formation in heteroarene-like indoles [ 71 , 72 ], imidazo[1,2 a ]pyridines [ 73 , 74 ], coumarines [ 75 ], benzothiazoles [ 76 ] and pyridines [ 77 ]; selenylation of naphthols [ 78 ], terminal alkenes [ 79 , 80 ] and alkynes [ 81 , 82 ] and sp 3 carbons [ 83 , 84 ]; and selenocyclization reactions have been reported [ 85 , 86 ]. In these protocols, in general, the substrate, the selenylating reagent and the photocatalyst are stimulated by visible light irradiation via single electron transfer (SET) reactions.…”

Section: Application Of Non-conventional Energy Sources In Organosele...mentioning

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: Application Of Non-conventional Energy Sources In Organosele...mentioning

confidence: 99%

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

et al. 2022

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“…Difunctionalization of alkenes enables rapid construction of complex molecules with broad applications in organic synthesis. In 2020, Yuan’s group [ 77 ] reported a mild and effective strategy for the synthesis of acyloxy selenides via visible-light-induced bifunctionalization of styrene with diaryl diselenides and carboxylic acid dibasic compounds ( Scheme 29 ). The work was carried out under white LEDs (20 W) with 4-methylstyrenes 141 , diphenyl diselenides, and acetic acids 142 as substrates, CH 3 CN as a solvent, and 1.0 mol% RB as the required catalyst.…”

Section: Application Of Dichalcogenides Under Visible-light Irradiationmentioning

confidence: 99%

Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology

et al. 2023

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Dichalcogenides (disulfides and diselenides), as reactants for organic transformations, are important and widely used because of their potential to react with nucleophiles, electrophilic reagents, and radical precursors. In recent years, in combination with photochemical technology, the application of dichalcogenides as stable radical reagents has opened up a new route to the synthesis of various sulfur- and selenium-containing compounds. In this paper, synthetic strategies for disulfides and diselenides and their applications with photochemical technology are reviewed: (i) Cyclization of dichalcogenides with alkenes and alkynes; (ii) direct selenylation/sulfuration of C−H/C−C/C−N bonds; (iii) visible-light-enabled seleno- and sulfur-bifunctionalization of alkenes/alkynes; and (iv) Direct construction of the C(sp)–S bond. In addition, the scopes, limitations, and mechanisms of some reactions are also described.

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“…In 2020, Yuan and co‐workers developed an interesting and mild protocol for synthesizing β‐acyloxyselenides 130 (Scheme 31). [56] Although procedures based on electrochemical protocols had been previously reported, the authors focused their work on finding a more efficient and greener procedure to synthesize these useful scaffolds, via visible light‐induced difunctionalization of styrenes 129 with a binary system of diaryl diselenides 11 and carboxylic acids 91 . A possible mechanism was been proposed.…”

Section: Selenylation Of Other Multiple Bondsmentioning

confidence: 99%

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

Rafique

Rampon

Azeredo

et al. 2021

The Chemical Record

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Organoselenium compounds constitute an important class of substances with applications in the biological, medicinal and material sciences as well as in modern organic synthesis, attracting considerable attention from the scientific community. Therefore, the construction of the C−Se bond via facile, efficient and sustainable strategies to access complex scaffolds from simple substrates are an appealing and hot topic. Visible light can be regarded as an alternative source of energy and is associated with environmentally‐friendly processes. Recently, the use of visible‐light mediated seleno‐functionalization has emerged as an ideal and powerful route to obtain high‐value selenylated products, with diminished cost and waste. This approach, involving photo‐excited substrates/catalyst and single‐electron transfer (SET) between substrates in the presence of visible light has been successfully used in the versatile and direct insertion of organoselenium moieties in activated and unactivated C(sp3)−H, C(sp2)−H, C(sp)−H bonds as well as C−heteroatom bonds. In most cases, ease of operation and accessibility of the light source (LEDs or commercial CFL bulbs) makes this approach more attractive and sustainable than the traditional strategies.

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Visible‐Light‐Induced Difunctionalization of Styrenes: An Efficient and Green Protocol for the Synthesis of β‐Acyloxyselenides

Cited by 14 publications

References 78 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

Synthesis and Application Dichalcogenides as Radical Reagents with Photochemical Technology

Light‐Mediated Seleno‐Functionalization of Organic Molecules: Recent Advances

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