Catalytic Synthesis Of Fluorinated Anilines

Tech ID: 24944 / UC Case 2015-140-0

Patent Status

Country Type Number Dated Case
Patent Cooperation Treaty Published Application WO2016183101 11/17/2016 2015-140
 

Additional Patent Pending

Brief Description

Molecules containing aniline and aniline derivatives are common in the pharmaceutical, agrochemical, and pigment industries and numerous methods for the preparation of anilines have been reported.  Aniline derivatives containing electron-withdrawing substituents are more valuable in medicinal chemistry because anilines are prone to oxidation.  The past methods to obtain fluorinated anilines, which also mitigate oxidation, have been limited and the yields were moderate.

 

UC Berkeley researchers have developed a reaction for the coupling of primary fluoroalkylamines with aryl bromides and aryl chlorides and occur in the presence of functional groups that are typically not tolerated by C-N coupling reactions. The reaction yield is high and can be conducted with low catalyst loadings for most substrates.

 

Suggested uses

  • Compounds containing aniline derivatives (e.g., medical and agrochemical compounds)
  • Pigments and chromophores

Advantages

  • Reaction has a wide substrate scope, occurs under mild conditions with inexpensive reagents, precatalysts and ligand
  • Occurs in high yield and can be conducted with low catalyst loadings (<0.50 mol%) for most substrates
  • Low nucleophilicity and low basicity of the weaker based used allow reaction to occur in the presence of functional groups that are not tolerated by C-N coupling reactions

Inventors

  • Hartwig, John F.

Other Information

Keywords

Catalyst; aniline; electron-withdrawing; fluorine; fluoroalkyl; arylation

Categorized As

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