A Ligand‐Enabled Palladium‐Catalyzed Highly para‐Selective Difluoromethylation of Aromatic Ketones

A practical and highly para‐selective C−H difluoromethylation of aromatic ketones has been developed by employing tetrakis(triphenylphosphine)palladium(0) as the catalyst and triphenylphosphine as the ligand. In addition to general aromatic ketones, this transformation was compatible with bioactive...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-11, Vol.57 (47), p.15597-15601
Main Authors: Tu, Guangliang, Yuan, Chunchen, Li, Yuting, Zhang, Jingyu, Zhao, Yingsheng
Format: Article
Language:English
Subjects:
Aromatic compounds
Benzophenone
Bioactive compounds
Carbonyl groups
Carbonyls
difluoromethylation
Ketones
Ketoprofen
ligand
Ligands
Palladium
site selectivity
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Summary:A practical and highly para‐selective C−H difluoromethylation of aromatic ketones has been developed by employing tetrakis(triphenylphosphine)palladium(0) as the catalyst and triphenylphosphine as the ligand. In addition to general aromatic ketones, this transformation was compatible with bioactive compounds and well‐known drugs, such as oxybenzone, ketoprofen, zaltoprofen, and propafenone. Moreover, a mechanistic study revealed that a palladium intermediate coordinated by a carbonyl group promotes highly para‐selective difluoromethylation. A para‐selective method for C−H difluoromethylation of aromatic ketones has been developed that employs tetrakis(triphenylphosphine)palladium(0) as a catalyst. The practical and highly selective transformation is compatible with a range of substrates, including conventional aromatic ketones, bioactive compounds, and well‐known drugs such as oxybenzone, ketoprofen, zaltoprofen, and propafenone.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201809788