Triel Bond Meets Hydrogen Bond: A Sulfonate–Fluoride Cooperative Platform for Mild Deuteration of Aryl Borons and Amines
By employing inexpensive CF<sub>3</sub>SO<sub>3</sub>CH<sub>3</sub>/NaF as cooperative activators, we achieved efficient deuterium incorporation (up to 96% yield, >95% D-incorporation) through a unique noncovalent activation mechanism involving synergistic triel-bonding (B···O) and hydrogen-bonding (O···H) interactions. This robust protocol features exceptional functional group tolerance, operational simplicity with commercially available reagents, and unprecedented versatility across all major classes of boron substrates (ArBF<sub>3</sub><sup>-</sup>, ArBpin, and ArB(OH)<sub>2</sub>), including direct one-pot deuteration of aryl amines, thereby establishing a cost-effective and broadly applicable platform for deuterium labeling.
Authors
- Qiuli Yao (ORCID: https://orcid.org/0000-0003-1059-2161)
- Boyu Yan
- Kaizhuo Lv
- Xiaoping Luo (ORCID: https://orcid.org/0000-0003-3004-6934)
- Dongfu Jiang
- Chuanling Zhao
Institutions
- Zunyi Medical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-10-27
- DOI
- https://doi.org/10.1021/acs.joc.5c01351
- Primary Topic
- Chemical Reactions and Isotopes
- Type
- article
- Field-Weighted Citation Impact
- 0.00