Theoretical Advances on the Mechanism of Transition Metal-Catalyzed C—F Functionalization

doi:10.6023/cjoc201810020

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 38-46.DOI: 10.6023/cjoc201810020 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

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过渡金属参与的C—F键官能团化反应机理研究进展

李园园^a,b,c, 王元鉴^a, 朱磊^d, 屈凌波^c, 蓝宇^c,d

a 重庆第二师范学院生物与化学工程学院重庆 400067;
b 重庆第二师范学院脂质资源与儿童日化品协同创新中心重庆 400067;
c 郑州大学化学与分子工程学院郑州 450006;
d 重庆大学化学化工学院重庆 401331

收稿日期:2018-10-18 修回日期:2018-12-05 发布日期:2018-12-07
通讯作者: 蓝宇 E-mail:lanyu@cqu.edu.cn
基金资助:
国家自然科学基金（Nos.21822303，21772020）、重庆市科委基金（基础研究与前沿探索）（No.cstc2018jcyjAX0827）、重庆第二师范学院科技协同创新平台建设（No.2017XJPT01）、重庆第二师范学院校级重点（No.KY201704A）、重庆第二师范学院博士启动基金（No.2017BSRC001）资助项目.

Theoretical Advances on the Mechanism of Transition Metal-Catalyzed C—F Functionalization

Li Yuanyuan^a,b,c, Wang Yuanjian^a, Zhu Lei^d, Qu Lingbo^c, Lan Yu^c,d

a College of Biological and Chemical Engineering, Chongqing University of Education, Chongqing 400067;
b Cooperative Innovation Center of Lipid Resources and Children's Daily Chemicals, Chongqing University of Education, Chongqing 400067;
c College of Chemistry and Molecular Engineering Engineering, ZhengZhou University, ZhengZhou 450006;
d School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 401331

Received:2018-10-18 Revised:2018-12-05 Published:2018-12-07
Contact: 10.6023/cjoc201810020 E-mail:lanyu@cqu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21822303, 21772020), the Basic and Frontier Research Project of Chongqing Science and Technology Commission (No. cstc2018jcyjAX0827), the Project of Science and Technology Collaborative Innovation Platform Construction of Chongqing University of Education (No. 2017XJPT01), the University-Level Key Projects of Chongqing University of Education (No. KY201704A), the Scientific Research Foundation of Chongqing University of Education (No. 2017BSRC001).

Organic fluorine chemistry has attracted considerable attention due to its unique character in the field of materials science, catalytic chemistry, medicine, fine chemicals and biochemistry, which majorly focus on the construction and cleavage of carbon-fluorine bonds. The transition metals are introduced to allow new possibilities for activating carbon-fluorine bonds and are gradually becoming an alternative way to synthesize numerous complex organics containing fluorine. In this review, the recent works on the theoretical mechanistic study for transition metals mediated carbon-fluorine bonds activation and cleavage are summarized. Meanwhile, the general modes of carbon-fluorine bonds activation have been concluded systematically, including the oxidative addition of carbon-fluorine bonds to transition metals, transition-metal-activated nucleophilic substitution, S_N2 type activation of carbon(sp³)-fluorine bonds and β-fluorine elimination, etc. The theoretical calculation shows that the reaction could be proceed by an oxidation addition mode, when the zero-valent nickel catalyst with strong reducibility is employed. However, if a zero-valent platinum catalyst is used, oxidation addition only occurs at extra activated carbon-fluorine bonds. In the reduction of polyfluorinated aromatic hydrocarbons by hydrogenated metal species, aromatic nucleophilic substitution between hydride and polyfluorinated aromatic hydrocarbons could occur to realize the activation of carbon-fluoride bonds. For carbon(sp³)-fluorine bonds, if “hard” Lewis base such as lithium or magnesium salt is employed, the carbon(sp³)-fluorine bonds can be activated via bimolecular nucleophilic substitution (S_N2). In addition, β-fluoride elimination is also frequently proposed in transition metal-catalyzed C—F functionalizations.

Key words: transition metal, C—F functionalization, reaction mechanism, fluorine chemistry

Cite this article

Li Yuanyuan, Wang Yuanjian, Zhu Lei, Qu Lingbo, Lan Yu. Theoretical Advances on the Mechanism of Transition Metal-Catalyzed C—F Functionalization[J]. Chin. J. Org. Chem., 2019, 39(1): 38-46.

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过渡金属参与的C—F键官能团化反应机理研究进展

Theoretical Advances on the Mechanism of Transition Metal-Catalyzed C—F Functionalization

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