Continuous activation of phenoxide and CF 3 I for multiple trifluoromethylations

The introduction of multiple trifluoromethyl (CF ) groups into aromatic compounds remains a significant challenge in synthetic chemistry. Here, we report an unprecedented visible light-promoted multiple trifluoromethylation of phenols using commercially available CF I. The key to success lies in our...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-12
Main Authors: Nakashima, Yusei, Kusano, Shinjiro, Inishi, Tsukasa, Nitta, Yasuyuki, Nishikata, Takashi
Format: Article
Language:English
Online Access:Get full text
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Summary:The introduction of multiple trifluoromethyl (CF ) groups into aromatic compounds remains a significant challenge in synthetic chemistry. Here, we report an unprecedented visible light-promoted multiple trifluoromethylation of phenols using commercially available CF I. The key to success lies in our discovery of a "continuous activation strategy" that enables sequential trifluoromethylations through single-electron transfer from photoexcited phenoxide to CF I until all or positions are occupied. This practical method provides access to previously inaccessible multi-CF -substituted phenols under mild conditions, opening revolutionary possibilities for the design of fluorine-containing functional materials.
ISSN:1364-548X