Dual Photoredox/Ni-Catalyzed Decarboxylative Coupling of α-Amino Acids to Uridine Derivatives

We present visible-light-mediated decarboxylative coupling of <i>N</i>-substituted glycine derivatives to the <i>N</i>3-position of <i>N</i>5-halo-uridine. The process utilizes dual iridium or organic dye and nickel catalysis to yield <i>N</i>3-amino methylene uridine derivatives. This work represents a new methodology to functionalize uridine derivatives as shown by 20 examples including biotin, fatty acid, and fluorinated residues among others.

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Publication Details

Journal
Organic Letters
Published
2025-07-26
DOI
https://doi.org/10.1021/acs.orglett.5c02253
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Dual Photoredox/Ni-Catalyzed Decarboxylative Coupling of α-Amino Acids to Uridine Derivatives

Anna M. Rydzik, Werngard Czechtizky, Marion Garreau, Enqin Fu et al.
Organic Letters
Radical Photochemical Reactions
article

Dual Photoredox/Ni-Catalyzed Decarboxylative Coupling of α-Amino Acids to Uridine Derivatives

Anna M. Rydzik, Werngard Czechtizky, Marion Garreau, Enqin Fu, Carlo Cassani, Christian Oettinger
article en

Abstract

We present visible-light-mediated decarboxylative coupling of <i>N</i>-substituted glycine derivatives to the <i>N</i>3-position of <i>N</i>5-halo-uridine. The process utilizes dual iridium or organic dye and nickel catalysis to yield <i>N</i>3-amino methylene uridine derivatives. This work represents a new methodology to functionalize uridine derivatives as shown by 20 examples including biotin, fatty acid, and fluorinated residues among others.

Organic LettersVol. 27(33)
AstraZeneca (South Korea) (KR), Pharmaron (United Kingdom) (GB), AstraZeneca (Australia) (AU), AstraZeneca (Netherlands) (NL), AstraZeneca (Switzerland) (CH), Institute of Immunology (HR), AstraZeneca (Finland) (FI)
Openalex Percentile: Top 86%
Radical Photochemical Reactions
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Dual Photoredox/Ni-Catalyzed Decarboxylative Coupling of α-Amino Acids to Uridine Derivatives — Anna M. Rydzik, Werngard Czechtizky, et al. · Organic Letters (2025) | TGRS Research Map | TGRS