Trifluoroacetic Acid Promotes Umpolung of 2‐Methylindole to Achieve C(<i>sp</i><sup>3</sup>)−H Activation
Abstract An umpolung strategy for the C( sp 3 )−H aminomethylation of 2‐methylindole has been developed using trifluoroacetic acid to induce the transformation, with aminals serving as precursors of iminium ion. Mechanistic studies have clearly shown that trifluoroacetic acid may play a pivotal role in this strategy. The utilization of readily available starting materials, mild reaction conditions, tolerance to complex functional groups, combine with yields of up to 98% and potential biological applications render this protocol applicable and useful for organic synthesis and medicinal chemistry.
Authors
- Chenggang Song
- Yan Hua (ORCID: https://orcid.org/0000-0001-8316-3937)
- Pan Zhou (ORCID: https://orcid.org/0000-0002-1862-4044)
- Lisha Jing
- Jingfa Zhang (ORCID: https://orcid.org/0000-0003-0601-4342)
- Kuo Li (ORCID: https://orcid.org/0000-0003-4571-4771)
- Bin Wang (ORCID: https://orcid.org/0000-0002-7331-2959)
- Yuyin Liu
- Hongmei Kong
Institutions
- Weifang Medical University (CN)
- Second Hospital of Shandong University (CN)
- Luye Pharma (China) (CN)
- Weifang Chinese Medicine Hospital (CN)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2024-10-28
- DOI
- https://doi.org/10.1002/adsc.202401128
- Citations
- 6
- Primary Topic
- Organic Chemistry Cycloaddition Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- Natural Science Foundation of Shandong Province
- Taishan Scholar Foundation of Shandong Province
- Northwest Fisheries Science Center