Synthesis of α-CF<sub>3</sub>-Substituted O-Heterocycles via Ligand-Controlled Cycloaddition of (<i>E</i>)-β-Trifluoromethylated Enones with π-Allylpalladium 1,4-Dipoles
Palladium-catalyzed and ligand-controlled cycloaddition of (<i>E</i>)-β-trifluoromethylated enones has been described, providing powerful synthetic strategies for two α-CF<sub>3</sub>-substituted O-heterocycles, tetrahydro-2<i>H</i>-pyrans and 5-oxaspiro[2.4]heptanes. The readily available substrates bearing various functional groups have shown variable product chemoselectivities. The salient features also included novel products with potential values and diverse derivatizations. The mechanistic investigations revealed the stereochemistry of the O-heterocyclic products.
Authors
- Hua‐Dong Xu (ORCID: https://orcid.org/0000-0002-4510-3754)
- Fen‐Er Chen (ORCID: https://orcid.org/0000-0002-6734-3388)
- Haoke Chu (ORCID: https://orcid.org/0000-0002-6201-0912)
- Junjie Zeng
- Xiaofang Lv (ORCID: https://orcid.org/0000-0003-2316-4537)
- Linhui Yang
- Yue Chen
- Feng Xiao-qing (ORCID: https://orcid.org/0009-0003-1841-6661)
Institutions
- Fudan University (CN)
- Changzhou University (CN)
- Chemical Synthesis Lab (SG)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-08-25
- DOI
- https://doi.org/10.1021/acs.joc.5c01706
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79
Funders
- National Natural Science Foundation of China
- Natural Science Research of Jiangsu Higher Education Institutions of China