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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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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cited_by cdi_FETCH-LOGICAL-c4398-68d1424e51b943db06e7c783d5cf1a9b11c98cc6859bc7b21e128c4ff6f74f773
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container_title Angewandte Chemie International Edition
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creator Tu, Guangliang
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description 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.
doi_str_mv 10.1002/anie.201809788
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source Wiley-Blackwell Read & Publish Collection
subjects Aromatic compounds
Benzophenone
Bioactive compounds
Carbonyl groups
Carbonyls
difluoromethylation
Ketones
Ketoprofen
ligand
Ligands
Palladium
site selectivity
title A Ligand‐Enabled Palladium‐Catalyzed Highly para‐Selective Difluoromethylation of Aromatic Ketones
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