Iron-Ceatalyzed Highly para-Selective Difluoromethylation of Arenes

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 successfull...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 142; no. 49; pp. 20524 - 20530
Main Authors Fan, Wei-Tai, Li, Yuting, Wang, Dongjie, Ji, Shun-Jun, Zhao, Yingsheng
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 09.12.2020
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
FUNCTIONALIZATION
META
ACTIVATION
OLEFINATION
ALKYLATION
C-H BORYLATION
NONCOVALENT INTERACTIONS
LIGAND
ENABLES
REGIOSELECTIVITY
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c09545