Tandem Oxidative Nucleophilic Hydrogen Substitution/B–O Cyclization Enables Chiral Near-Infrared N,O,B-Chelated BODIPYs
We report a mild, modular tandem strategy that transforms readily available B-substituted BODIPYs into a new class of N,O,B-chelated BODIPYs with intense near-infrared absorption/emission. The key transformation involves oxidative nucleophilic substitution of α-hydrogens (ONSH) followed by intramolecular B-O cyclization, operating with diverse ketones (acetophenones, indanones, tetralones, acenaphthenone). X-ray crystallography reveals a tetrahedral boron center that is inherently stereogenic. Chiral resolution by HPLC and circular dichroism spectroscopy confirm the optical activity of the enantiomers.
Authors
- Qinghua Wu (ORCID: https://orcid.org/0000-0002-7252-7990)
- L Wang
- Y U E J I He (ORCID: https://orcid.org/0009-0005-9525-4082)
- Huiquan Zuo
- Erhong Hao (ORCID: https://orcid.org/0000-0001-7234-4994)
- Zhengxin Kang (ORCID: https://orcid.org/0000-0003-0784-2932)
- Hui Li (ORCID: https://orcid.org/0000-0001-9198-3951)
- Xing Guo (ORCID: https://orcid.org/0000-0003-3647-6572)
- Wenxin Gu (ORCID: https://orcid.org/0009-0005-3578-4479)
- Hua Wang
- Lijuan Jiao
- Yuting Zhang
Institutions
- Ministry of Education of the People's Republic of China (CN)
- Anhui University of Traditional Chinese Medicine (CN)
- Anhui Normal University (CN)
- Anhui Polytechnic University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-07-27
- DOI
- https://doi.org/10.1021/acs.orglett.6c02925
- Primary Topic
- Luminescence and Fluorescent Materials
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Anhui Province