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Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides†
Martin B. Johansen,Anders T. Lindhardt
Organic & Biomolecular Chemistry Pub Date : 01/27/2020 00:00:00 , DOI:10.1039/C9OB02635E
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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