Access to 1-Aryl-pyrazolin-5-ones via Photocatalytic Chemoselective Tri/Difluoromethylation and Cyclization of <i>N</i>-Methacryloyl Aldehyde Hydrazones
A photocatalytic trifluoromethylation and 5<i>-endo-trig</i> cyclization of (<i>E</i>)-<i>N</i>'-arylidene-<i>N</i>-phenylmethacrylohydrazides was developed for the construction of trifluoromethylated pyrazolin-5-one derivatives using easily available trifluoromethyl thianthrenium triflate (TT-CF<sub>3</sub><sup>+</sup>OTf<sup>-</sup>) as the trifluoromethyl source. This protocol exhibits a broad substrate scope and excellent chemoselectivity. The utility of the current strategy is further highlighted by its application in the late-stage modification of drug molecules. Furthermore, difluoromethylative cyclization was realized using PhI(O<sub>2</sub>CCHF<sub>2</sub>)<sub>2</sub> under similar conditions.
Authors
- Changduo Pan (ORCID: https://orcid.org/0000-0001-5878-3835)
- Yanmei Gong
- Miao Zeng
Institutions
- Jiangsu University of Technology (CN)
- Clean Energy (United States) (US)
- Changzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-30
- DOI
- https://doi.org/10.1021/acs.joc.5c00861
- Citations
- 12
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 9.49
Funders
- Qinglan Project of Jiangsu Province of China
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department