4.8 Article

Iron-Ceatalyzed Highly para-Selective Difluoromethylation of Arenes

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 49, Pages 20524-20530

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c09545

Keywords

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Funding

  1. Natural Science Foundation of China [21772139]
  2. Jiangsu Province Natural Science Found for Distinguished Young Scholars [BK20180041]
  3. PAPD Project

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Direct functionalization of a C-H bond at either the meta or para position by only changing the catalyst system poses a significant challenge. We herein report the [Fe(TPP)Cl]-enabled, selective, C-H difluoromethylation of arenes using BrCF2CO2 Et as the difluoromethylation source, which successfully altered the selectivity from the meta to the para position. A preliminary mechanistic study revealed the iron porphyrin complex not only activated the aromatic ring but also induced para selectivity due to the influence of ligand sterics.

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