Nickel-Catalyzed Monofluoromethylation of Aryl Boronic Acids

Aryl boronic acids can be monofluoromethylated under nickel catalysis. The utility of this method is demonstrated by the monofluoromethylation of a borylated and acyl‐protected derivative of the statin drug ezetimibe. Mechanistic investigations indicate that a fluoromethyl radical is involved in the...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2015-05, Vol.54 (20), p.6003-6007
Main Authors: Su, Yi-Ming, Feng, Guang-Shou, Wang, Zhen-Yu, Lan, Quan, Wang, Xi-Sheng
Format: Article
Language:English
Subjects:
Aromatic compounds
aryl boronic acid
Boronic Acids - chemistry
Catalysis
Catalysts
Derivatives
Drugs
Fluorometers
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Molecular Structure
monofluoromethylation
Nickel
Nickel - chemistry
Organometallic Compounds - chemistry
Radicals
Utilities
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Summary:Aryl boronic acids can be monofluoromethylated under nickel catalysis. The utility of this method is demonstrated by the monofluoromethylation of a borylated and acyl‐protected derivative of the statin drug ezetimibe. Mechanistic investigations indicate that a fluoromethyl radical is involved in the NiI/NiIII catalytic cycle.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201412026