CF3Br参与的三氟甲基化反应研究进展

doi:10.6023/cjoc202108058

摘要/Abstract

三氟甲基化反应是向有机物中引入氟原子的重要方法. 综述了近年来以CF₃Br为三氟甲基源的三氟甲基化反应研究进展, 重点介绍了各类反应涉及到的具体方法、每种方法的特点、适用范围及可能的机理, 并对CF₃Br作为三氟甲基源的三氟甲基化反应前景作出展望.

关键词: 三氟溴甲烷, 三氟甲基化, 亲核性, 自由基

Trifluoromethylation reaction is a critical method to install fluorine atom into organic molecules. The recent advances in trifluoromethylation with CF₃Br as trifluoromethyl source are summarized. Various trifluoromethylation methods involving CF₃Br are presented. Their characteristics, scope and limitations as well as the reaction mechanism are discussed in detail, and a perspective on the further development by using CF₃Br as trifluoromethyl source is put forward.

Key words: bromotrifluoromethane, trifluoromethylation, nucleophilicity, free radical

引用此文

马然松, 邓周斌, 王克虎, 黄丹凤, 胡雨来, 闾肖波. CF₃Br参与的三氟甲基化反应研究进展[J]. 有机化学, 2022, 42(2): 353-362.

Ransong Ma, Zhoubin Deng, Kehu Wang, Danfeng Huang, Yulai Hu, Xiaobo Lü. Research Progress of Trifluoromethylation Involving CF₃Br[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 353-362.

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图/表 18

图式1. 常见三氟甲基试剂

Scheme 1. Common trifluoromethyl reagents

图式2. 常见三氟甲基化试剂的制备流程

Scheme 2. Preparation process of common trifluoromethyl reagents

. 图示3 CF3Br与醛、酮的电解反应

Scheme 3. Electrochemical reaction of CF3Br with aldehydes and ketones

图式4. CF3Br与TMSCl的电解反应

Scheme 4. Electrochemical reaction of CF3Br with TMSCl

图式5. 锌促进的Barbier反应

Scheme 5. Zinc promoted Barbier reaction

图式6. 锌促进的Barbier反应

Scheme 6. Indium promoted Barbier reaction

图式7. P(NEt2)3促进的亲核三氟甲基化反应

Scheme 7. Nucleophilic trifluoromethylation promoted by P(NEt2)3

图式8. 二氧化硫阴离子诱导CF3Br与芳烃的反应

Scheme 8. Reactions of CF3Br with arenes induced by sulphur dioxide radical anion

图式9. 二氧化硫阴离子诱导CF3Br与二硫醚的反应

Scheme 9. Reactions of CF3Br with disulphides induced by sulphur dioxide radical anion

图式10. 吡唑过硫化物与CF3Br的反应

Scheme 10. Reaction of pyrazole persulfide with CF3Br

图式11. 钯催化CF3Br与(杂)芳烃的反应

Scheme 11. Palladium catalyzed reactions of CF3Br with (hetero)arenes

图式12. Pt/C催化RfBr与芳烃的反应

Scheme 12. Pt/C catalyzed reactions of RfBr with arenes

图式13. 镍催化自由基串联反应机理

Scheme 13. Mechanism of nickel catalyzed radical tandem reaction

图式14. 镍催化RfBr与芳烃的反应

Scheme 14. Nicke catalyzed reactions of RfBr with arenes

图式15. 锌促进RfBr与烯烃的反应

Scheme 15. Zinc promoted reactions of RfBr with olefins

图式16. 钴促进的CF3Br与烯烃的反应

Scheme 16. Cobalt promoted reactions of CF3Br with olefins

图式17. 可见光诱导CF3Br与烯、炔烃的氢三氟甲基化反应

Scheme 17. Visible-light-induced hydrotrifluoromethylation of alkenes and alkynes with CF3Br

图式18. 超声辐射促进CF3Br参与的三氟甲基化反应

Scheme 18. Ultrasonic radiation promotes trifluoromethylation involving CF3Br

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CF₃Br参与的三氟甲基化反应研究进展

Research Progress of Trifluoromethylation Involving CF₃Br

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