4.7 Article

Copper(II)-Catalysed Aerobic Oxidative Coupling of Arylamines with Hexafluoroisopropanol: An Alternative Methodology for Constructing Fluorinated Compounds

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 1, Pages 268-274

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001048

Keywords

Copper(II) catalysis; Fluorination; Aerobic oxidative coupling; Arylamines; Hexafluoroisopropanol

Funding

  1. National Natural Science Foundation of China [21772091]
  2. Priority Academic Program Development of Jiangsu Higher Education Institutions

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A new method for generating fluoroalkylated arylamines under mild conditions with a wide substrate scope and excellent yields was developed using copper(II)-catalysed aerobic oxidative coupling. Preliminary studies suggest the reaction occurs via a radical mechanism, and the protocol offers an alternative green route for constructing fluorinated compounds by using atmospheric O2 as an oxidant.
The selective functionalisation of arylamine derivatives with hexafluoroisopropanol through copper(II)-catalysed aerobic oxidative coupling was developed to generate various fluoroalkylated arylamines under mild conditions. This method has a wide substrate scope with excellent functional group tolerance and provides the fluorinated products in good to excellent yields. Furthermore, preliminary studies indicate that this reaction occur via a radical mechanism. This protocol, which uses atmospheric O-2 as an oxidant, provides an alternative green route for constructing fluorinated compounds.

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