Copper/Silver-Mediated Decarboxylative Trifluoromethylation of α,β-Unsaturated Carboxylic Acids with CF3SO2Na

Yin, Jun; Li, Yaming; Zhang, Rong; Kun, Jin; Duan, Chunying

doi:10.1055/s-0033-1338578

Cited by 16 publications

(7 citation statements)

References 1 publication

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“…Cyclic voltammetry (CV) was used to provide a study of the redox potentials of the substrates (Figure ). The CV experiments showed the oxidation peak of CF 3 SO 2 Na at 1.2 V, which is in accordance with the CF 3 SO 2 radical formation (Figure , curve b). , The enol acetate 1l did not show considerable reactivity in anodic oxidation under the potential below 1.4 V (Figure , curve c). The mixture of CF 3 SO 2 Na with enol acetate 1l showed an irreversible anodic wave at 1.1 V, indicating that the mechanism involved a highly reactive species formed in the electron-transfer step (Figure , curve d).…”

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confidence: 77%

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

et al. 2021

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The electrochemical synthesis of fluorinated ketones from enol acetates and RfSO2Na in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded via perfluoroalkyl radical generation from sodium perfluoroalkyl sulfinate followed by addition to the enol acetate and transformation of the resulting C radical to a fluorinated ketone. The method is applicable to a wide range of enol acetates and results in the desired products in yields of 20 to 85%.

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confidence: 77%

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

et al. 2021

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“…Difluorobenzodioxole (195) being important class of compounds, however, their synthesis is challenging due to the use of hazardous reagents and limited substrate scope. In this regard, Friesen and co-workers in 2020 developed an efficient strategy for their synthesis using easily available catechols (193) in two steps (Scheme 59) through conversion into thionobenzodioxoles (194), followed by desulfurative fluorination with silver(I) fluoride. [143] To have insight into the reaction pathway, an interesting intermediate oxocarbenium ion (197) was detected by 19F NMR spectroscopy in case of amino acid derivatives (197a, 197b).…”

Section: Chemcatchemmentioning

confidence: 99%

“…Taking lead from there, in 2014, Duan and co‐workers developed stereoselectively decarboxylative trifluoromethylation of α,β‐unsaturated carboxylic acids (271) by copper/silver catalysis under mild reaction conditions (Scheme 90). [193] Reaction was capable of tolerating various highly electron donating, electron withdrawing along with heterocyclic functionalities and afforded the desired trifluoromethylated product (272) in good to moderate yield with excellent E‐selectivity.…”

Section: Trifluoromethylation Reactionmentioning

confidence: 99%

Emergence of Ag as a Catalyst of Choice for Fluorination and Trifluoromethylation Reactions

2023

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Carbon‐fluorine bond being highly polar in nature, its presence in pharmaceutically active molecules has huge impact on their chemical and physical properties. However, fluorine being highly electronegative and small in size, limits its nucleophilicity to the large extent; hence the incorporation of fluorine in the organic molecules is not an easy task. Due to this, demand for a suitable catalyst for fluorination reaction has been raised, which lowers the activation energy of these reactions and makes C−F/CF3 bond formation reaction kinetically more feasible. Silver being a late transition metal catalyst has been efficiently used to catalyze several reactions in the organic chemistry and has the substantial potential to catalyze the fluorination reactions. This Review shows the silver catalyzed fluorination and trifluoromethylation reactions for the synthesis of F/CF3 containing aromatic, aliphatic and heterocyclic compounds. All the sections have been elaborated using general discussion of the method, exploration of substrate scope, insight into the mechanistic studies and the shortcomings of the methods. After reading this Review article the readers can develop a detailed understanding of concept of silver metal catalyzed fluorination and trifluoromethylation reactions which can be explored for synthesizing molecules of biological interest.

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“…Additionally, Duan and co-workers [139] discovered a copper/silver-catalyzed decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids with CF 3 SO 2 Na. This reaction proceeded efficiently for a wide range of alkyl and aryl-substituted α,β-unsaturated carboxylic acids derivatives with excellent E / Z selectivity (Scheme 76).…”

Section: Reviewmentioning

confidence: 99%

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

Shi

et al. 2019

Beilstein J. Org. Chem.

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Fluorine chemistry plays an increasingly important role in pharmaceutical, agricultural, and materials industries. The incorporation of fluorine-containing groups into organic molecules can improve their chemical and physical properties, which attracts continuous interest in organic synthesis. Among various reported methods, transition-metal-catalyzed fluorination/fluoroalkylation has emerged as a powerful method for the construction of these compounds. This review attempts to describe the major advances in the transition-metal-catalyzed incorporation of fluorine, trifluoromethyl, difluoromethyl, trifluoromethylthio, and trifluoromethoxy groups reported between 2011 and 2019.

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Copper/Silver-Mediated Decarboxylative Trifluoromethylation of α,β-Unsaturated Carboxylic Acids with CF3SO2Na

Cited by 16 publications

References 1 publication

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates

Emergence of Ag as a Catalyst of Choice for Fluorination and Trifluoromethylation Reactions

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

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