Bromine-Enabled Halogen-Bond-Promoted Electrochemical 16O/18O-Incorporation for Skeletal Editing of N -Heterocycles
Abstract Incorporating oxygen into N-heterocycles with simultaneous isotopic labeling remains challenging. Here, we report a metal-, oxidant-, and base-free electrochemical platform using water as the oxygen source for 16O/18O incorporation. Bromide acts as both a redox mediator and halogen-bond activator, with generated Br2 enhancing substrate electrophilicity and promoting hydroxide attack. The method enables skeletal editing of tetrazines and pyrazines and peripheral editing of tetrazoles and triazines, affording 18O-labeled products with up to 99% enrichment and broad functional-group tolerance.
Authors
- Chenglin Ding
- Tianruo Shen (ORCID: https://orcid.org/0000-0001-5417-0783)
- Yimin Jiang (ORCID: https://orcid.org/0009-0004-9615-6153)
- Yu Zheng (ORCID: https://orcid.org/0009-0003-1485-8008)
- Qilin Yang
- Shuangqiang Tang
- Hong Xu
- Junsheng Pu
- Hongbao Sun
- Jie Liu (ORCID: https://orcid.org/0000-0001-8391-7807)
- Guizhen Zhang
Institutions
- Sichuan University (CN)
- National Supercomputing Center of Tianjin (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-27
- DOI
- https://doi.org/10.1021/acs.orglett.6c04072
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Department of Science and Technology of Sichuan Province
- Natural Science Foundation of Sichuan Province