Copper-Catalyzed Defluorinative [3 + 2] Cyclization of Amidines and Trifluoromethyl Carbenoids for the Synthesis of 5-Fluoroimidazoles
A Cu-catalyzed [3 + 2] cyclization of amidines with trifluoromethyldiazo compounds is described. The reaction affords 5-fluoroimidazoles in good yields by cleaving dual C-F bonds in a CF<sub>3</sub> group. Using 2-aminoazo heterocycles as the substrates, various annelated imidazoles containing a fluorine atom were also constructed by this method without changing the conditions. The resultant 5-fluoroimidazoles show high reactivity toward S<sub>N</sub>Ar reactions with a series of nucleophiles.
Authors
- Lei Zhou (ORCID: https://orcid.org/0000-0002-8391-8452)
- Hao Tan (ORCID: https://orcid.org/0000-0002-8783-5929)
- Jinxin Liu (ORCID: https://orcid.org/0000-0002-7933-258X)
- Yonghong Zhang (ORCID: https://orcid.org/0000-0002-7740-9408)
Institutions
- Sun Yat-sen University (CN)
- Green Chemistry (PL)
- Xinjiang University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-18
- DOI
- https://doi.org/10.1021/acs.orglett.4c03594
- Citations
- 5
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.04
Funders
- Major Research Plan