A Copper-Catalyzed Approach to Access (Het)Aryl/Alkenyl Selenoglycosides Employing Electrophilic Glycosyl Selenosulfonates
A general and mild copper-catalyzed strategy is described for the synthesis of structurally diverse (hetero)aryl and alkenyl selenoglycosides. This protocol utilizes bench-stable glycosyl selenosulfonates as electrophilic donors, enabling the direct coupling of nucleophilic (het)aryl/alkenyl boronic acids and esters, thereby significantly expanding the chemical space of selenoglycosides. The synthetic utility of the method is highlighted by the successful construction of a clinical SGLT2 inhibitor empagliflozin analogue.
Authors
- Hao Sun (ORCID: https://orcid.org/0000-0003-3670-3739)
- Qi Zhang (ORCID: https://orcid.org/0000-0002-5203-8778)
- Weitao Yan (ORCID: https://orcid.org/0000-0001-8963-7013)
- Chunfa Xu (ORCID: https://orcid.org/0000-0001-7232-6956)
- Shiping Wang (ORCID: https://orcid.org/0009-0009-9153-8415)
- Xin Zhang (ORCID: https://orcid.org/0000-0001-9669-7866)
- Ji Guo
- Ruo Wang
Institutions
- Fujian Medical University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Shanxi University of Traditional Chinese Medicine (CN)
- Fujian Provincial Hospital (CN)
- University of Chinese Academy of Sciences (CN)
- Fuzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-06-13
- DOI
- https://doi.org/10.1021/acs.orglett.6c02175
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00