Continuous activation of phenoxide and CF3I for multiple trifluoromethylations

• 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
• ISSN: 1364-548X; 1364-548X
• DOI: 10.1039/d4cc06221c

The introduction of multiple trifluoromethyl (CF3) 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 CF3I. 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 CF3I until all ortho or para positions are occupied. This practical method provides access to previously inaccessible multi-CF3-substituted phenols under mild conditions, opening revolutionary possibilities for the design of fluorine-containing functional materials.The introduction of multiple trifluoromethyl (CF3) 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 CF3I. 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 CF3I until all ortho or para positions are occupied. This practical method provides access to previously inaccessible multi-CF3-substituted phenols under mild conditions, opening revolutionary possibilities for the design of fluorine-containing functional materials.