Stereospecific Photoredox‐Catalyzed Vinylations to Functionalized Alkenes and C ‐Glycosides **
Abstract: We report an efficient radical‐mediated C−C coupling through photoredox‐catalyzed reactions of 4‐alkyl‐dihydropyridines (DHPs) and vinylbenziodoxol (on) es (VBX, VBO). This transition‐metal‐free and mild photocatalytic method has excellent functional group tolerance and affords vinylated products in good yields, with complete retention of the alkene configuration. The utility of the methodology is demonstrated by the diastereoselective synthesis of C‐vinyl glycosides. Preliminary mechanistic studies suggest that the C−C bond formation is stereospecific and proceeds through a concerted radical coupling transition state.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Stereospecific Photoredox‐Catalyzed Vinylations to Functionalized Alkenes and C ‐Glycosides ** ; day:12 ; month:04 ; year:2023 ; extent:7
Angewandte Chemie ; (12.04.2023) (gesamt 7)
- Creator
- DOI
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10.1002/ange.202301368
- URN
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urn:nbn:de:101:1-2023041315021251297953
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:53 AM CEST
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Associated
- Bhaskar Pal, Kumar
- Di Tommaso, Ester Maria
- Inge, A. Ken
- Olofsson, Berit
Other Objects (12)
Stereospecific Photoredox‐Catalyzed Vinylations to Functionalized Alkenes and C ‐Glycosides **
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Red-light-mediated copper-catalyzed photoredox catalysis promotes regioselectivity switch in the difunctionalization of alkenes
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Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes
Visible-light photoredox catalysis enabled bromination of phenols and alkenes
Asymmetric Ni-Catalyzed Hydrocarbamoylation of Alkenes
Asymmetric Zirconium-Catalyzed Alkylalumination of Alkenes
Stereospecific Photoredox‐Catalyzed Vinylations to Functionalized Alkenes and C ‐Glycosides **
Nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes
Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams
Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine
Red-light-mediated copper-catalyzed photoredox catalysis promotes regioselectivity switch in the difunctionalization of alkenes
The photoredox catalyzed Meerwein arylation
Palladium-Catalyzed Vinylborylation of Alkenes
Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides
Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes
Visible-light photoredox catalysis enabled bromination of phenols and alkenes
Asymmetric Ni-Catalyzed Hydrocarbamoylation of Alkenes
Asymmetric Zirconium-Catalyzed Alkylalumination of Alkenes
Stereospecific Photoredox‐Catalyzed Vinylations to Functionalized Alkenes and C ‐Glycosides **
Nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes
Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams
Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine
Red-light-mediated copper-catalyzed photoredox catalysis promotes regioselectivity switch in the difunctionalization of alkenes
The photoredox catalyzed Meerwein arylation
Palladium-Catalyzed Vinylborylation of Alkenes
Photoredox-Catalyzed Decarboxylative Alkynylation of Peptides
Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes
Visible-light photoredox catalysis enabled bromination of phenols and alkenes
Asymmetric Ni-Catalyzed Hydrocarbamoylation of Alkenes