Abstract
Because of the lack of naturally occurring pathways to form C-F bonds, and the high toxicity and/or explosive nature of the fluorination reagents (HF and F2), chemists have to seek alternative reagents and relevant fluorination and fluoroalkylation methods to construct oragnofluorides that we widely use today. The direct transition-metal mediated/catalyzed trifluoroethylation of organic scaffolds, such as arylboronic acids or esters, aryl iodides, arene, alkynes, and alkenes, has been encouragingly established. This review narrates the recent progress of the reactions with using CF3CH2X (X = I, OTs, NH2) as the trifluoroethyl reagents in the past few years. Given the high potential of trifluoroethyl-containing compounds as bioactive agents, these synthetic methodologies will find wide applications in the life-science-related fields. To overcome the negative intrinsic factors of the current trifluoroethylation reagents in these reactions, future research work will doubtlessly focus on the development of effective catalytic systems, the design of new reagents, and the investigation of the possible CF3CH2-metal intermediates.
Keywords: Trifluoroethylation, metal, reagent, fluorine.
Current Organic Chemistry
Title:Recent Progress in Metal-Mediated Trifluoroethylation
Volume: 19 Issue: 16
Author(s): Jia-Bin Han, Jian-Hong Hao, Cheng-Pan Zhang and Hua-Li Qin
Affiliation:
Keywords: Trifluoroethylation, metal, reagent, fluorine.
Abstract: Because of the lack of naturally occurring pathways to form C-F bonds, and the high toxicity and/or explosive nature of the fluorination reagents (HF and F2), chemists have to seek alternative reagents and relevant fluorination and fluoroalkylation methods to construct oragnofluorides that we widely use today. The direct transition-metal mediated/catalyzed trifluoroethylation of organic scaffolds, such as arylboronic acids or esters, aryl iodides, arene, alkynes, and alkenes, has been encouragingly established. This review narrates the recent progress of the reactions with using CF3CH2X (X = I, OTs, NH2) as the trifluoroethyl reagents in the past few years. Given the high potential of trifluoroethyl-containing compounds as bioactive agents, these synthetic methodologies will find wide applications in the life-science-related fields. To overcome the negative intrinsic factors of the current trifluoroethylation reagents in these reactions, future research work will doubtlessly focus on the development of effective catalytic systems, the design of new reagents, and the investigation of the possible CF3CH2-metal intermediates.
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Cite this article as:
Han Jia-Bin, Hao Jian-Hong, Zhang Cheng-Pan and Qin Hua-Li, Recent Progress in Metal-Mediated Trifluoroethylation, Current Organic Chemistry 2015; 19 (16) . https://dx.doi.org/10.2174/1385272819666150122235905
DOI https://dx.doi.org/10.2174/1385272819666150122235905 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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