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

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...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-02, Vol.18 (7), p.1417-1425
Main Authors: Johansen, Martin B, Lindhardt, Anders T
Format: Article
Language:English
Subjects:
Additives
Antidepressants
Chemical compounds
Copper
Copper compounds
Functional groups
Iodides
NMR
Nuclear magnetic resonance
Optimization
Organic chemistry
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Summary: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. Low cost and widely available Cu 2 O has been identified as a superior catalyst towards decarboxylative aromatic trifluoromethylations in the absence of ligands and additives.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob02635e