Guo Quanping, Wang Mengran, Liu Hong, Wang Rui, Xu Zhaoqing
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Science, Lanzhou University, 199 West Donggang Road, Lanzhou, 730000, China.
Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4747-4751. doi: 10.1002/anie.201800767. Epub 2018 Mar 25.
The first visible-light-promoted dearomative fluoroalkylation of β-naphthols was realized without the assistance of any transition-metal catalysts or external photosensitizers. Inexpensive fluoroalkyl iodides were directly used as efficient fluoroalkylation reagents under very mild reaction conditions. The scope of this process was found to be general and broad, and both trifluoromethyl and perfluoroalkyl groups (-C F , -C F , and -C F ) were installed in excellent yields. Preliminary mechanistic studies suggest that visible-light-promoted intermolecular charge transfer within the naphtholate-fluoroalkyl iodide electron donor-acceptor (EDA) complex induces a single electron transfer in the absence of photocatalysts.
在没有任何过渡金属催化剂或外部光敏剂协助的情况下，实现了首例可见光促进的β-萘酚去芳构化氟烷基化反应。在非常温和的反应条件下，廉价的氟代烷基碘化物被直接用作有效的氟烷基化试剂。发现该反应过程适用范围广泛，三氟甲基和全氟烷基（-CF₃、-C₂F₅和-C₃F₇）均能以优异的产率引入。初步机理研究表明，在萘酚盐-氟代烷基碘电子给体-受体（EDA）络合物中，可见光促进的分子间电荷转移在无光催化剂的情况下诱导了单电子转移。
