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Continuous activation of phenoxide and CF3I for multiple trifluoromethylations
Chemical Communications ( IF 4.3 ) Pub Date : 2024-12-17 , DOI: 10.1039/d4cc06221c
Yusei Nakashima, Shinjiro Kusano, Tsukasa Inishi, Yasuyuki Nitta, Takashi Nishikata

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.

中文翻译:


连续激活苯氧化物和 CF3I 以进行多种三氟甲基化



在芳香族化合物中引入多个三氟甲基 (CF3) 基团仍然是合成化学中的一个重大挑战。在这里,我们报道了使用市售 CF3I 的前所未有的可见光促进酚的多重三氟甲基化。成功的关键在于我们发现了一种“连续激活策略”,该策略通过从光激发苯氧到 CF3I 的单电子转移实现连续的三氟甲基化,直到所有邻位或对位位置都被占据。这种实用的方法提供了在温和条件下以前无法获得的多 CF3-取代酚,为含氟功能材料的设计开辟了革命性的可能性。
更新日期:2024-12-20
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