Intramolecular Fe(II)-catalyzed N-O or N-N bond formation from aryl azides.
Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.
Stokes
Benjamin J
BJ
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Vogel
Carl V
CV
Urnezis
Linda K
LK
Pan
Minjie
M
Driver
Tom G
TG
D001386:Azides / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005296:Ferrous Compounds / Q000737:chemistry*; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry
C441200:1,2-benzisoxazole; D001386:Azides; D001965:Bromides; D005296:Ferrous Compounds; D007191:Indazoles; D007555:Isoxazoles; D011720:Pyrazoles