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Tóth BL, Kovács S, Sályi G, et al. Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation. Angew Chem Int Ed Engl. 2016;55(6):1988-92doi: 10.1002/anie.201510555.
Tóth, B. L., Kovács, S., Sályi, G., & Novák, Z. (2016). Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation. Angewandte Chemie (International ed. in English), 55(6), 1988-92. https://doi.org/10.1002/anie.201510555
Tóth, Balázs L, et al. "Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation." Angewandte Chemie (International ed. in English) vol. 55,6 (2016): 1988-92. doi: https://doi.org/10.1002/anie.201510555
Tóth BL, Kovács S, Sályi G, Novák Z. Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation. Angew Chem Int Ed Engl. 2016 Feb 05;55(6):1988-92. doi: 10.1002/anie.201510555. Epub 2016 Jan 14. PMID: 26762554.
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Angew Chem Int Ed Engl. 2016 Feb 05;55(6):1988-92. doi: 10.1002/anie.201510555. Epub 2016 Jan 14.

Mild and Efficient Palladium-Catalyzed Direct Trifluoroethylation of Aromatic Systems by C-H Activation.

Angewandte Chemie (International ed. in English)

Balázs L Tóth, Szabolcs Kovács, Gergő Sályi, Zoltán Novák

Affiliations

  1. MTA-ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Faculty of Science, Pázmány Péter stny. 1/A, H-1117, Budapest, Hungary.
  2. MTA-ELTE "Lendület" Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Faculty of Science, Pázmány Péter stny. 1/A, H-1117, Budapest, Hungary. [email protected].

PMID: 26762554 DOI: 10.1002/anie.201510555

Abstract

The introduction of trifluoroalkyl groups into aromatic molecules is an important transformation in the field of organic and medicinal chemistry. However, the direct installation of fluoroalkyl groups onto aromatic molecules still represents a challenging and highly demanding synthetic task. Herein, a simple trifluoroethylation process that relies on the palladium-catalyzed C-H activation of aromatic compounds is described. With the utilization of a highly active trifluoroethyl(mesityl)iodonium salt, the developed catalytic method enables the first highly efficient and selective trifluoroethylation of aromatic compounds. The robust catalytic procedure provides the desired products in up to 95 % yield at 25 °C in 1.5 to 3 hours and tolerates a broad range of functional groups. The utilization of hypervalent reagents opens new synthetic possibilities for direct alkylations and fluoroalkylations in the field of transition-metal-catalyzed C-H activation.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: C−H activation; anilides; iodonium salts; palladium; trifluoroethylation

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