Shen Ting, Xie Qiong, Li Yuanyuan, Zhu Jun
State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation, Center of Chemistry for Energy Materials (iChEM), and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, P. R. China.
Chem Asian J. 2019 Jun 3;14(11):1937-1940. doi: 10.1002/asia.201900294. Epub 2019 Apr 29.
Fluorine is the most electronegative element in the periodic table. Thus, activation of the carbon-fluorine (C-F) bond, the strongest single bond to carbon, has attracted considerable interest from both experimentalists and theoreticians. In comparison with numerous approaches to activate C-F bonds, the aromaticity-promoted method is less developed. Herein, we demonstrate that the C-F bond activation could be achieved by a facile tautomerization, benefitting from aromaticity, which can stabilize both the transition states and products. Our findings highlight an important application of aromaticity in the C-F bond activation, providing experimentalists with an alternative approach to activate C-F bonds.
