Photoredox-Catalyzed <i>C</i>‑Indolyl/Quinolyl\nGlycosylation from 2‑Styrylisocyanides and Glycosyl Bromides

Indole and quinoline structures are present in numerous\nbiologically\nactive molecules, making the synthesis of their glycosylation products\na subject of extensive research and interest in drug development.\nHere, we report a photoredox strategy for the synthesis of <i>C</i>-indolyl and <i>C</i>-quinolyl glycosides using\n2-styrylisocyanides and glycosyl bromides as building blocks. This\napproach offers mild reaction conditions, high α-selectivity,\nand scalability for large-scale reactions. The radical cyclization\nmode switching from 5-<i>exo</i>-trig to 6-<i>endo</i>-trig is achieved by selecting the substituents on the 2-vinyl group.\nThis strategy enriches the toolbox of heterocyclic glycosylation methods\nand benefits advances in research on heteroaryl-based pharmaceuticals.

Publication Details

Journal
Figshare
Published
2024-09-16
DOI
https://doi.org/10.1021/acs.orglett.4c03050.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Photoredox-Catalyzed C‑Indolyl/Quinolyl\nGlycosylation from 2‑Styrylisocyanides and Glycosyl Bromides

Figshare
Radical Photochemical Reactions
article

Photoredox-Catalyzed C‑Indolyl/Quinolyl\nGlycosylation from 2‑Styrylisocyanides and Glycosyl Bromides

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Abstract

Indole and quinoline structures are present in numerous\nbiologically\nactive molecules, making the synthesis of their glycosylation products\na subject of extensive research and interest in drug development.\nHere, we report a photoredox strategy for the synthesis of <i>C</i>-indolyl and <i>C</i>-quinolyl glycosides using\n2-styrylisocyanides and glycosyl bromides as building blocks. This\napproach offers mild reaction conditions, high α-selectivity,\nand scalability for large-scale reactions. The radical cyclization\nmode switching from 5-<i>exo</i>-trig to 6-<i>endo</i>-trig is achieved by selecting the substituents on the 2-vinyl group.\nThis strategy enriches the toolbox of heterocyclic glycosylation methods\nand benefits advances in research on heteroaryl-based pharmaceuticals.

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