Three-component aminoselenation of alkenes <i>via</i> visible-light enabled Fe-catalysis

Huang, Binbin; Li, Yanan; Yang, Chao; Xia, Wujiong

doi:10.1039/c9gc04163j

Cited by 93 publications

(51 citation statements)

References 60 publications

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“…Furthermore, moderate yields were obtained with electronically diversified aromatic and aliphatic diselenides. [128] Similarly, aminoselenation of alkene 66 was realized with 1,2,3-triazoles 65 and selenium sources with stereospecific antiaddition by Zhu et. al.…”

Section: Organoselenium Reagents As Regioselective and Stereoselectivmentioning

confidence: 99%

“…As per mechanistic pathway proposed by the authors, the reaction of both the substrates mediates through phenylseleniranium intermediates produced by selective attack of electrophilic species PhSe(OTf) on the alkenes as per the substrate followed by the regioselective attack of water and then final oxidation by 1-fluoropyridinium reagent. [126] In 2020, Yang and Xia [128] reported visible-light photocatalyzed difunctionalization of alkene with diselenide which was mediated through photoexcitable Fe-amine complex (Scheme 27). This complex interacts with diselenides under the influence of blue LED light carried out in ethylacetate at room temperature to give the active selenium species.…”

Section: Organoselenium Reagents As Regioselective and Stereoselectivmentioning

confidence: 99%

“…In 2020, Yang and Xia [128] reported visible‐light photocatalyzed difunctionalization of alkene with diselenide which was mediated through photoexcitable Fe‐amine complex (Scheme 27). This complex interacts with diselenides under the influence of blue LED light carried out in ethylacetate at room temperature to give the active selenium species.…”

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

“…However, the reaction did not work well for aliphatic amines, as its iron‐amine complex might be photo‐inactive in blue light wavelength region. Furthermore, moderate yields were obtained with electronically diversified aromatic and aliphatic diselenides [128] …”

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

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Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

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Section: Organoselenium Reagents As Regioselective and Stereoselectivmentioning

confidence: 99%

Section: Organoselenium Reagents As Regioselective and Stereoselectivmentioning

confidence: 99%

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

Section: Overview On Selenium‐catalyzed/selenium Incorporating Transfmentioning

confidence: 99%

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Insights into the Recent Synthetic Advances of Organoselenium Compounds

2021

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“…The reactions occurred smoothly to produce diverses eleniumcontaining compounds owing to itsb road substrate scope (Scheme 10). [23] In the mechanisticstudies, anovel photoexcitable complex [FeBr 3 •NHRAr], generated in situ by simplym ixing FeBr 3 with aryl amine, was postulated for the first time as the key intermediate, which couldb ee xcited by blue LED light. One radicalP hSeC ando ne cation PhSe + were obtain through the cleavage of the SeÀSe bond oxidized by the [FeBr 3 •NHRAr]* via aS ET process.…”

Section: Light-induced Iron Photoredox Catalysis In Addition Reactionmentioning

confidence: 99%

Light Runs Across Iron Catalysts in Organic Transformations

Zhou

Meng

et al. 2020

Chemistry A European J

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Over the past decades, organometallic complexes with precious elements, such as ruthenium and iridium, are widelyu sed as visible-light photoredox catalysts. Recently,m ore and more complexes based on earthabundant andi nexpensive elementsh ave been used as sensitizers in photochemistry.A lthough the photoexcited state lifetimes of iron complexes are typically shortert han those of traditional photosensitizers, the utilization of iron catalysts in photochemistry has sprung up owing to their abundance, low price, nontoxicity,a nd novel properties, including exhibiting ligand to metal charge transfer states. This concept focuses on recent advances in light-driven iron catalysis in organic transformations, including iron/ photoredox dual catalysis,l ight-inducedi ron photoredox catalysis and light-induced generation of active iron catalysts. The prospectf or the future of this field is also discussed.

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