Transition Metal-Free Synthesis of meta-Bromo- and meta-Trifluoromethylanilines from Cyclopentanones by a Cascade Reaction


Staudt M., Cetin A. , Bunch L.

CHEMISTRY-A EUROPEAN JOURNAL, vol.28, no.10, 2022 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 28 Issue: 10
  • Publication Date: 2022
  • Doi Number: 10.1002/chem.202102998
  • Title of Journal : CHEMISTRY-A EUROPEAN JOURNAL
  • Keywords: anilines, drug synthesis, electrocyclic ring-opening, new methodology, transition metal-free, CATALYZED C-N, CONVERSION

Abstract

Anilines are key constituents in biologically active compounds and often obtained from transition metal-catalyzed coupling of an aryl halide with an amine. In this work, we report a transition metal-free method for the synthesis of meta-bromo- and meta-trifluoromethylanilines starting from 3-tribromomethylcyclopentanone or 3-(2-bromo-2-chloro-1,1,1-trifluoroethyl)cyclopentanone, respectively. The scope of the transformation is shown by application of primary, secondary and aromatic amines. The reaction proceeds in acceptable to high yields (20-81 %), and allows for the synthesis of anilines with substitution patterns otherwise difficult to access.