2-Pyridone-Enhanced Mn-Catalysis for the Synthesis of <i>ortho</i>-Deuterated Aromatic Nitriles
We herein present a method for the synthesis of <i>ortho</i>-deuterated aryl nitrile using Mn(CO)<sub>5</sub>Br as catalyst with CH<sub>3</sub>OD as deuteratium source, where the structure of aryl imidates is used for interconversion with a cyanide group. This method features a broad substrate range and excellent functional group tolerance, allowing late modification of various complex molecules with good yields and deuterium incorporation. Mechanistic studies suggest that 2-pyridone is crucial to the success of this chemistry, serving as an endogenous base that enhances the rate of hydrogen isotope exchange.
Authors
- Jian‐Fei Bai (ORCID: https://orcid.org/0000-0002-9128-5819)
- Zhanghua Gao (ORCID: https://orcid.org/0000-0002-6950-8609)
- Zhi‐Jiang Jiang (ORCID: https://orcid.org/0000-0003-2323-1840)
- Jia Chen (ORCID: https://orcid.org/0000-0003-1541-2617)
- You Zhou (ORCID: https://orcid.org/0000-0001-9250-0982)
- Yanran Liu (ORCID: https://orcid.org/0000-0003-0062-4473)
- Qian Tao (ORCID: https://orcid.org/0000-0002-8170-969X)
- Jinfeng Zheng
Institutions
- Ningbo University of Technology (CN)
- Zhejiang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-15
- DOI
- https://doi.org/10.1021/acs.orglett.4c04061
- Citations
- 5
- Primary Topic
- Chemical Reactions and Isotopes
- Type
- article
- Field-Weighted Citation Impact
- 1.04
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangsu Province
- Natural Science Foundation of Ningbo