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

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.Danish Research Council (DFF/FSS); University of Copenhagen; Higher Education Commission of Turkey (TUBITAK) [1059B191800125]We would like to thank the Danish Research Council (DFF/FSS), the University of Copenhagen, and the Higher Education Commission of Turkey (TUBITAK) (No: 1059B191800125) for financial support