Redox-Neutral Synthesis of Selenoesters by Oxyarylation of Selenoalkynes under Mild Conditions

Baldassari, Lucas L.; Mantovani, Anderson C.; Senoner, Samuel; Maryasin, Boris; Maulide, Nuno; Lüdtke, Diogo S.

doi:10.1021/acs.orglett.8b02544

Cited by 26 publications

(7 citation statements)

References 55 publications

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“…The selenium moiety can be introduced in an organic substrate through electrophilic, nucleophilic and radical pathways [13,14,15,16,17] . The versatile reactivity of selenium species provides eco‐friendly reaction conditions, functional compatibility and high atom economy [18,19,20,21] .…”

Section: Introductionmentioning

confidence: 99%

“…[12] The selenium moiety can be introduced in an organic substrate through electrophilic, nucleophilic and radical pathways. [13,14,15,16,17] The versatile reactivity of selenium species provides eco-friendly reaction conditions, functional compatibility and high atom economy. [18,19,20,21] Because of these features, the application of organoselenium compounds is not restrict to pharmacological studies, but also on seleniumcatalyzed reactions.…”

Section: Introductionmentioning

confidence: 99%

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Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

et al. 2020

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This review article deals with organic synthesis from the perspective of selenium-77 nuclear magnetic resonance (NMR) spectroscopy. Different types of organic reactions are briefly discussed, incorporating mechanism aspects through 77 Se NMR observable intermediates and byproducts. The 77 Se NMR experiments are demonstrated in terms of structural characterization and new insights for organic reactions. The ability to visualize different molecules in a reaction mixture provides a facile and versatile route for the development of synthetic organoselenium compounds. Thus, the review describes the strategies accomplished mainly in the past five years in the syntheses and applications of the organoselenium compounds, focusing on 77 Se NMR spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

et al. 2020

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“…More recently,o ur group developed ar edox-neutral synthesis of a-arylated selenoesters through the activation of selenoacetylenes by acid catalysis. [44] The treatment of selenoacetylenes with catalytic amounts of TfOH leads to the formation of as elenium-stabilized vinyl cation,w hich is captured by an aryl sulfoxide and then undergoes a[ 3,3]-sigmatropicr earrangement to deliver the final a-arylated selenoester product. This protocoll ed to the synthesis of 33 compounds in good yields (Scheme 20).…”

Section: Synthesis Of Selenoestersf Rom Selenoacetylenesmentioning

confidence: 99%

Synthetic Approaches to Selenoesters

Baldassari

Lüdtke

2021

Chemistry A European J

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Selenoesters are compounds of great synthetic relevance since they can be used in several types of chemical transformations and mainly due to their great capacity in the formation of acyl radicals. Therefore, the scientific community has been developing several methods for the synthesis of this class of molecules. This review will address the synthesis of these compounds from different starting materials, such as carboxylic acids derivatives (acid chlorides and anhydrides), aldehydes, selenoacetylenes and miscellaneous methods.

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“…Two recent examples highlighted the potential of these compounds in organic synthesis, the iodoalkyne behaving either as a catalyst or as an activator . The analogues thio- and selenoalkynes are known to be stable useful synthons in organic synthesis, − but the σ-hole donor properties of sulfur and selenium in these derivatives have never been considered. It is thus worth exploring and possibly exploiting iodo- and more specifically thio- and selenoalkynes as XB or ChB (chiral) donors.…”

Section: Introductionmentioning

confidence: 99%

Disubstituted Ferrocenyl Iodo- and Chalcogenoalkynes as Chiral Halogen and Chalcogen Bond Donors

et al. 2020

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Asymmetric catalysis based on halogen and chalcogen bonds (XB and ChB) is in its infancy, and the search for new chiral XB and ChB donors represents a crucial step toward its development. In this context, we designed and prepared new motifs containing three key substructures: namely, regions of electron charge density depletion centered on iodine and chalcogen atoms, the ethynyl functionality, and the planar chiral ferrocenyl platform. Nine ferrocenyl iodoalkynes were prepared as pure enantiomers by asymmetric synthesis. The XB donor property of racemic ferrocenyl iodoalkynes was demonstrated in solution in two benchmark reactions: the Ritter reaction and the benzoxazole synthesis from thioamides. In contrast, the ferrocenyl chalcogenoalkynes were far less active in these reactions. The potential of racemic and enantiopure ferrocenyl iodoalkynes as XB donors was also confirmed by X-ray diffraction analysis, showing I•••C contacts between the electropositive σ-hole of the iodine atom and electron-rich π clouds for all crystal structures studied in the solid state.

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Redox-Neutral Synthesis of Selenoesters by Oxyarylation of Selenoalkynes under Mild Conditions

Cited by 26 publications

References 55 publications

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

Synthetic Approaches to Selenoesters

Disubstituted Ferrocenyl Iodo- and Chalcogenoalkynes as Chiral Halogen and Chalcogen Bond Donors

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