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Issue 7, 2020
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Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

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Abstract

A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.

Graphical abstract: Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

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Supplementary files

Article information


Submitted
11 Dec 2019
Accepted
27 Jan 2020
First published
27 Jan 2020

Org. Biomol. Chem., 2020,18, 1417-1425
Article type
Paper

Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

M. B. Johansen and A. T. Lindhardt, Org. Biomol. Chem., 2020, 18, 1417
DOI: 10.1039/C9OB02635E

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