Journal
ORGANIC LETTERS
Volume 24, Issue 2, Pages 702-707Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c04148
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Funding
- Natural Science Foundation of China [21801050, 22171056]
- Featured Innovation Project of Guangdong University [2020KTSCX094]
- Guangdong Natural Science Foundation [2021A1515010072]
- Guangzhou Municipal Science and Technology Project [202102020784]
- University (Institute) Joint Funding (High-level University) Basic Research Project [202102010397, 202102010468]
- project of State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medicial University [QJHKY[2022]389]
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This Letter presents a novel approach for the 1,2-dicarbofunctionalization of trifluoromethyl alkenes. The method involves a cascade reaction of pyridinium salts with trifluoromethyl alkenes, leading to the formation of pyridines bearing a trifluoromethyl-substituted quaternary center.
Although trifluoromethyl alkenes have great synthetic potential, their 1,2-difunctionalization has been a challenge. In this Letter, we disclose the first 1,2-dicarbofunctionalization of trifluoromethyl alkenes with pyridinium salts via a cascade process involving a base-promoted [3 + 2] cycloaddition followed by a visible-light-mediated Norrish-type-II fragmentation. This protocol allows for the formation of pyridines bearing a trifluoromethyl-substituted quaternary center in moderate to excellent yields under mild conditions.
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