The development of sustainable trifluoromethylations of enamides is of great interest to the pharmaceutical industry. Herein, we demonstrate a sustainable direct electrochemical trifluoromethylation method in a microflow cell, using Langlois reagent, without the need for a supporting electrolyte, oxidants, or any additive under mild conditions. This method can be applied to various substrates with a yield of up to 84%. Additionally, the batch process yielded significantly less (22%), highlighting the microflow cell's efficiency.
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http://dx.doi.org/10.1021/acs.oprd.4c00311 | DOI Listing |
ACS Sens
December 2024
Ocean College, Zhejiang University, Zhoushan 316021, China.
The reference electrode's performance is essential for ensuring the accuracy of electrochemical sensors in marine environments. Yet, the many existing reference electrodes can exhibit sensitivity to salinity variations, potentially leading to inaccuracies in the measurement process. Herein, we have designed a reliable solid-state reference electrode by introducing SiO-stabilized 1-methyl-3-octylimidazolium bis(trifluoromethyl sulfonyl)imide ([Cmim] [Ntf]) into a P(VdF--HFP) matrix with a SPEEK/[Cmim] [Ntf] coated Ag/AgCl as substrate.
View Article and Find Full Text PDFACS Polym Au
December 2024
Luxembourg Institute of Science and Technology, 5 Avenue des Hauts-Fourneaux, L-4362 Esch-sur-Alzette, Luxembourg.
High ionic conductivity poly(ionic liquid)s (PILs) are of growing interest for their thermal and electrochemical stability, processability, and potential in safe, flexible all-solid-state electrochemical devices. While various approaches to enhance the ionic conductivity are reported, the influence of cation substituents is rarely addressed. Moreover, some of the asymmetric anions recently developed for high-conductivity ionic liquids were never tested in PILs.
View Article and Find Full Text PDFOrg Process Res Dev
November 2024
Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
The development of sustainable trifluoromethylations of enamides is of great interest to the pharmaceutical industry. Herein, we demonstrate a sustainable direct electrochemical trifluoromethylation method in a microflow cell, using Langlois reagent, without the need for a supporting electrolyte, oxidants, or any additive under mild conditions. This method can be applied to various substrates with a yield of up to 84%.
View Article and Find Full Text PDFChem Sci
December 2024
Department of Chemistry, Chung-Ang University 84 Heukseok-ro, Dongjak-gu Seoul 06974 Republic of Korea
Recent advancements in eco-friendly radical fluoroalkylation have substituted traditional two-electron-based reactions. However, the radical trifluoromethylation of terminal alkynes remains a significant challenge, primarily due to the high reactivity of alkenyl radical intermediates, which predominantly engage in reactions other than the desired elimination. In this work, we have developed an electrochemical trifluoromethylation method for terminal alkynes, facilitating the efficient formation of CF-alkynes.
View Article and Find Full Text PDFChem Asian J
November 2024
Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya, 464-8601, Japan . nagoya-u.ac.jp.
β-(Trifluoromethyl)styrenes are potentially useful building blocks for the synthesis of organofluorine compounds because their electron-deficient C=C double bonds can undergo diverse transformations. One of the most practical methods for preparing β-(trifluoromethyl)styrenes is the decarboxylative trifluoromethylation of readily available cinnamic acid derivatives using the Langlois reagent as a less expensive trifluoromethyl source. We revisited the electrochemical decarboxylative trifluoromethylation of cinnamic acid derivatives to identify modified conditions that reduce the loading of the Langlois reagent without additional additives.
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