Superacid-catalysed α-deuteration of ketones with D <sub>2</sub> O
In this study, we present a superacid catalyzed protocol for the α-deuteration of ketones with D<sub>2</sub>O using [Ph<sub>3</sub>C]<sup>+</sup>[B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup> as a pre-catalyst to generate <i>in situ</i> the superacidic species [D]<sup>+</sup>[B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub>]<sup>-</sup>. The features of this catalytic process include simple manipulation, high deuteration efficiency (up to 99%), excellent functional group compatibility and a broad substrate scope, including 30 substrates comprising common building blocks and bioactive molecules like pentoxifylline. Moreover, the avoidance of toxic reagents enables sustainable access to deuterated products, demonstrating the method's practical potential for use in mechanistic studies and pharmaceutical applications.
Authors
- Zhenhua Jia (ORCID: https://orcid.org/0000-0002-5154-4839)
- Teck‐Peng Loh (ORCID: https://orcid.org/0000-0002-2936-337X)
- Kaichen Xu (ORCID: https://orcid.org/0000-0003-4957-3144)
- Hong Yuan (ORCID: https://orcid.org/0000-0002-1942-6744)
- Jinling Li (ORCID: https://orcid.org/0000-0002-4558-1254)
- Zhenguo Zhang
Institutions
- Nanyang Technological University (SG)
- Henan University of Technology (CN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00683j
- Citations
- 1
- Primary Topic
- Chemical Reactions and Isotopes
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- Agency for Science, Technology and Research
- Nanyang Technological University