Stereoselective Palladium-Catalyzed C(sp3)-H Arylation of Furanose Carboxamides
Abstract We report the first stereoselective palladium-catalyzed C(sp3)–H arylation of furanose carboxamides at the C3 position, achieving 2,3-cis selectivity without prefunctionalization. Optimized conditions provide diverse arylated furanosides in yields up to 61%, and we established efficient protocols for removing the directing group and deprotecting benzyl groups. DFT calculations rationalize the stereochemical outcome, and this method enables access to suzetrigine analogs, expanding the synthetic toolkit for carbohydrate-based drug discovery.
Authors
- Linlin Li
- Mayssa Zayene (ORCID: https://orcid.org/0009-0003-9943-3198)
- Vincent Gandon (ORCID: https://orcid.org/0000-0003-1108-9410)
- Pascal Retailleau (ORCID: https://orcid.org/0000-0003-3995-519X)
- Franck Le Bideau (ORCID: https://orcid.org/0000-0003-4365-4525)
- Samir Messaoudi (ORCID: https://orcid.org/0000-0002-4994-9001)
- Angélique Ferry (ORCID: https://orcid.org/0000-0001-9141-5479)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-27
- DOI
- https://doi.org/10.1021/acs.orglett.6c04358
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- CY Cergy Paris Université
- China Scholarship Council
- Centre National de la Recherche Scientifique
- Grand Équipement National De Calcul Intensif
- École Polytechnique, Université Paris-Saclay