Nucleophilic Substitution of Aromatic Halides with Amines under High Pressure

Article abstract of DOI:10.1246/cl.1987.1187

The reaction of aromatic chlorides, bromides and iodides with various primary or secondary amines in a tetrahydrofuran solution under high pressure of 6-12 kbar gave the corresponding secondary and tertiary aromatic amines. 1,4-Diazabicyclo<2.2.2>octane and quinuclidine gave N-aryl quaternary ammonium halides in high yields in contrast to the low reactivity of acyclic tertiary amines.