Recent Advances in the Electrochemical Defluorinative Transformations of C-F Bonds

Wan, Qinhui1,2,4; Liu, Rui-Xue1,2,3; Zhang, Zhongyi1,2; Wu, Xia-Die1,2; Hou, Zhong-Wei1,2; Wang, Lei1,2,4

2024-04-01

10.1002/cjoc.202400058

CHINESE JOURNAL OF CHEMISTRY   影响因子和分区

1001-604X

1614-7065

["Comprehensive SummaryOrganic fluorine compounds are ubiquitous and pivotally important organic molecules, yet their activation and transformation have long been a formidable challenge due to the high energy and low reactivity of C-F bonds. Organic electrosynthesis, an environmentally benign synthetic method in organic chemistry, enables a myriad of chemical transformations without the need for external redox reagents. In recent years, organic electrochemistry has emerged as a powerful tool for achieving the activation and transformation of C-F bonds in fluorine-containing compounds. This review aims to succinctly recapitulate the latest advancements in the electrochemical defluorinative transformations of C-F bonds and to delve into the reaction design, mechanistic insights, and developmental prospects of these methods.Key ScientistsIn 1959, Lund was the first to pioneer the electroreduction of CF3 to CH3 group. Electrochemistry has lately provided new opportunities for efficient conversion of organic fluorides. In 2020, Zhou and coworkers discovered the electrochemical defluorinative carboxylation of alpha-CF3 alkenes. Lambert and colleagues reported electrophotocatalytic defluorinative amination of aryl fluorides. Electrochemical hydrodefluorination of trifluoromethylketones was developed by Lennox and coworkers in 2021. In the same year, Wang and Guo disclosed electrochemical radical defluorinative alkylation of alpha-CF3 alkenes with Katritzky salts as the alkyl radical precursors. Subsequently, Wu and Liao described a transition-metal-free, site-selective C-F arylation of polyfluoroarenes with (het)arenes using paired electrophotocatalysis. In 2023, numerous efforts were made to achieve electrochemical C-F bond activation. Xia and Guo developed an organoboron-controlled method for the chemoselective electrochemical sequential (deutero)hydrodefluorination of trifluoroacetamides.","The latest advancements in the electrochemical defluorinative transformations of C-F bonds have been summarized and mainly concentrate on the reaction design, mechanistic insights, and developmental prospects of these methods.double dagger image"]

Organic electrochemistry Electroreduction Defluorination C-F bond activation Organic fluorine compounds

SCI

英语

ESI高被引

其他

National Natural Science Foundation of China["22101201","22071171"] ; null[LQ22B020005] ; null[LZ22B020003]

Chemistry

Chemistry, Multidisciplinary

WOS:001206886700001

WILEY-V C H VERLAG GMBH

CHEMISTRY

Web of Science

1.Taizhou Univ, Adv Res Inst, Jiaojiang 318000, Zhejiang, Peoples R China
2.Taizhou Univ, Sch Pharmaceut Sci, Jiaojiang 318000, Zhejiang, Peoples R China
3.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
4.Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou 311121, Zhejiang, Peoples R China

Wan, Qinhui,Liu, Rui-Xue,Zhang, Zhongyi,et al. Recent Advances in the Electrochemical Defluorinative Transformations of C-F Bonds[J]. CHINESE JOURNAL OF CHEMISTRY,2024.

Wan, Qinhui,Liu, Rui-Xue,Zhang, Zhongyi,Wu, Xia-Die,Hou, Zhong-Wei,&Wang, Lei.(2024).Recent Advances in the Electrochemical Defluorinative Transformations of C-F Bonds.CHINESE JOURNAL OF CHEMISTRY.

Wan, Qinhui,et al."Recent Advances in the Electrochemical Defluorinative Transformations of C-F Bonds".CHINESE JOURNAL OF CHEMISTRY (2024).