Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4<i>H</i>-pyrans
A three-component annulation reaction and trifluoromethylation for the construction of 3-(trifluoromethyl)-4<i>H</i>-pyrans using β-CF<sub>3</sub>-1,3-enynes, BrCF<sub>2</sub>CO<sub>2</sub>Et, and sulfoxonium ylides as readily available substrates has been developed. This metal-free process involves two C-F bond cleavages of β-CF<sub>3</sub>-1,3-enynes and a CF<sub>3</sub> group generated <i>in situ</i> from BrCF<sub>2</sub>CO<sub>2</sub>Et. This method is applicable to the late-stage modification of pharmaceutically active molecules.
Authors
- An‐Xin Wu (ORCID: https://orcid.org/0000-0001-7673-210X)
- Xiang‐Long Chen (ORCID: https://orcid.org/0009-0005-0754-5809)
- Yan‐Dong Wu (ORCID: https://orcid.org/0000-0003-0589-7155)
- Dongsheng Yang
- Yong‐Xing Tang
- Lisheng Wang (ORCID: https://orcid.org/0000-0001-6202-5463)
- Chun‐Yan Wu (ORCID: https://orcid.org/0009-0004-1347-7972)
- Yong-Dong Du
Institutions
- Central China Normal University (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-27
- DOI
- https://doi.org/10.1021/acs.orglett.4c03266
- Citations
- 7
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.46
Funders
- National Natural Science Foundation of China
- Higher Education Discipline Innovation Project