Citation: Li Man, Kang Huiying, Xue Xiao-Song, Cheng Jin-Pei. Computational Study of the Trifluoromethyl Radical Donor Abilities of CF₃ Sources[J]. Acta Chimica Sinica, ;2018, 76(12): 988-996. doi: 10.6023/A18080334 shu

Computational Study of the Trifluoromethyl Radical Donor Abilities of CF₃ Sources

a.
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, China
b.
Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, China

Corresponding author: Xue Xiao-Song, xuexs@nankai.edu.cn
Received Date: 14 August 2018
Available Online: 8 December 2018
Fund Project: the State Key Laboratory on Elemento-Organic Chemistry the Fundamental Research Funds for the Central Universities the National Natural Science Foundation of China 21390400Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) the National Natural Science Foundation of China 21772098Project supported by the National Natural Science Foundation of China (Nos. 21772098, 21390400), Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), the State Key Laboratory on Elemento-Organic Chemistry, and the Fundamental Research Funds for the Central Universities

Figures(9)

Organic compounds containing trifluoromethyl (CF₃) group(s) are widely prevalent in biochemical and medicinal science. This is mainly due to the fact that the trifluoromethyl group often improves the metabolic stability and lipophilicity of biologically active compounds. The need of efficient methods for the incorporation of this group into target molecules has spurred research to discover new, practical CF₃ sources. Among various CF₃ sources, the radical trifluoromethylating reagents has provided a strong driving force for the discovery of the novel trifluoromethylation reactions, and contributed enormously to the efficient synthesis of various CF₃-containing compounds. Although a wide variety of radical CF₃ sources are now available to organic chemists, little attention has been paid to assess their trifluoromethyl radical donor abilities (TR^·DA). Moreover, the available radical reagents show a very rich and diverse reactivity. The establishment of an extensive scale to quantify their CF₃ radical donating abilities should be of great value for both the rational design of novel reagents and the judicious selection of appropriate reagent to explore new radical reactions. Herein, we present a systematic computational study of the homolytic X―CF₃ bond dissociation enthalpies of 35 radical trifluoromethylating reagents by using the SMD-M06-2X/[6-311++G(2df, 2p)-Def2-QZVPPD]//SMD-M06-2X/[6-31+G(d)-LANL2DZ] method, aiming to provide an energetic guide for estimating their trifluoromethyl radical donor abilities. A comprehensive TR^·DA scale was constructed, which covers a range from -21.5 to 95.2 kcal·mol^-1. The effects of the frequently used activators including single electron transfer reagents and halogen/chalcogen-bond donors on trifluoromethyl radical donor abilities were investigated. The results show that single electron transfer is the most efficient way to promote the CF₃ radical release. We expect that the results of this study could be highly valuable for the mechanistic understanding and the rational design of novel CF₃ sources and new radical trifluoromethylation reactions.
- radical trifluoromethylating reagent,
- homolytic bond dissociation enthalpy,
- structure-reactivity relationship,
- halogen bond,
- DFT calculation
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Computational Study of the Trifluoromethyl Radical Donor Abilities of CF₃ Sources