Iron(II) bromide-catalyzed synthesis of benzimidazoles from aryl azides.
The identity of the ortho-substituent of an aryl azide influences its reactivity toward transition metals. Substitution of a vinyl group with an imine disables rhodium(II)-mediated C-H amination and triggers a Lewis acid mechanism catalyzed by iron(II) bromide to facilitate benzimidazole formation.
Shen
Meihua
M
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Driver
Tom G
TG
D000814:Aniline Compounds / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry; D001562:Benzimidazoles / Q000138:chemical synthesis*; D001965:Bromides / Q000737:chemistry; D005296:Ferrous Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry
D000814:Aniline Compounds; D001386:Azides; D001547:Benzaldehydes; D001562:Benzimidazoles; D001965:Bromides; D005296:Ferrous Compounds; D012238:Rhodium