4.6 Article

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

期刊

ORGANIC & BIOMOLECULAR CHEMISTRY
卷 18, 期 7, 页码 1417-1425

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02635e

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资金

  1. Independent Research Fund Denmark Technology and Production [4148-00031]
  2. Carlsberg Foundation [CF17-0517]
  3. Danish National Research Foundation
  4. DNRF [118]
  5. Aarhus University

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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.

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