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
- Field-Weighted Citation Impact
- 0.00