TEMPO-Mediated Electrochemical α-Allylation of Tetrahydroisoquinolines
A C(sp<sup>3</sup>)-H allylation of tetrahydroisoquinolines has been developed by combining Shono oxidation with a vinylogous Mannich-type reaction. TEMPO was used as the electrocatalyst to lower the electrode potential, improving functional group compatibility. This method provided a practical and efficient tandem procedure for the α-allylation of tetrahydroisoquinolines. The reaction proceeded through the formation of an iminium cation intermediate, which was generated in situ by anodic oxidation, followed by nucleophilic addition of 2-allylazaarenes.
Authors
- Cong Ma (ORCID: https://orcid.org/0000-0001-7568-1347)
- Youliang He
- Ping Fang (ORCID: https://orcid.org/0000-0002-3421-2613)
- Zhen‐Hua Wang (ORCID: https://orcid.org/0000-0002-0603-707X)
- Hao Xu (ORCID: https://orcid.org/0000-0001-9685-7364)
- Tian‐Sheng Mei (ORCID: https://orcid.org/0000-0002-4985-1071)
- Huilin Liu
Institutions
- Central China Normal University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-25
- DOI
- https://doi.org/10.1021/acs.orglett.5c00738
- Citations
- 6
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 5.62
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Science and Technology Commission of Shanghai Municipality
- National Key Research and Development Program of China