Easily Handled NaBAr<sup>F</sup><sub>4</sub> Catalyzed Selective Electrophilic Deuteration Method for C(sp<sup>2</sup>)–H Bond of Aryl Amines
Deuterated aryl amines are increasingly sought after in pharmaceuticals, particularly in the development of deuterated drugs. Traditional methods for their synthesis often involve harsh conditions or preprepared reagents. This study introduces a mild, metal-free method for the selective deuteration of aryl amines, utilizing deuterium oxide (D<sub>2</sub>O) and a commercially available catalyst, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate (NaBAr<sup>F</sup><sub>4</sub>). The reaction is performed under moderate conditions and is compatible with a wide range of substrates, including sensitive functional groups. Mechanistic studies highlight the crucial role of noncoordinated Na<sup>+</sup> in catalysis, underscoring the broader potential of NaBAr<sup>F</sup><sub>4</sub> and weakly coordinating anions (WCAs) in synthetic chemistry. This method offers an efficient and sustainable approach to synthesizing deuterated aryl amines.
Authors
- Wanqing Wu (ORCID: https://orcid.org/0000-0001-5151-7788)
- Huanfeng Jiang (ORCID: https://orcid.org/0000-0002-4355-0294)
- Jiahao Wu (ORCID: https://orcid.org/0009-0004-4484-5934)
- Xiangwen Tan
Institutions
- Key Laboratory of Guangdong Province (CN)
- South China University of Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-03
- DOI
- https://doi.org/10.1021/acs.joc.5c00066
- Primary Topic
- Chemical Reactions and Isotopes
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- National Key Research and Development Program of China
- Basic and Applied Basic Research Foundation of Guangdong Province