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Synthesis of tri(di)fluoroethylanilines via copper-catalyzed coupling reaction of tri(di)fluoroethylamine with (hetero)aromatic bromides

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Abstract

We have realized the first Ullmann type coupling reaction of tri(di)fluoroethylamine with (hetero)aromatic bromides, employing 5–20 mol% Cu2O and an oxalamide ligand [N-(2,4,6-trimethoxyphenyl)acetamide]. This efficient and practical method has the following features: (i) avoids the use of an expensive catalyst; (ii) does not require anhydrous solvent and strict air extrusion; (iii) uses bench stable and inexpensive (hetero)aromatic bromides; (iv) is suitable for the synthesis of fluoroalkylated hetero-aromatic substrates; (v) is suitable for gram-scale synthesis. This work also shows the “negative fluorine effect” for the alkylamines in the copper catalysed coupling reactions.

Graphical abstract: Synthesis of tri(di)fluoroethylanilines via copper-catalyzed coupling reaction of tri(di)fluoroethylamine with (hetero)aromatic bromides

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Publication details

The article was received on 19 Oct 2019, accepted on 04 Nov 2019 and first published on 04 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02271F
Org. Biomol. Chem., 2019, Advance Article

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    Synthesis of tri(di)fluoroethylanilines via copper-catalyzed coupling reaction of tri(di)fluoroethylamine with (hetero)aromatic bromides

    S. Chen, H. Wang, W. Jiang, P. Rui and X. Hu, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB02271F

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