C−H Bond Amination from a Ferrous Dipyrromethene Complex

Abstract

In this Communication, we report an intramolecular C-H bond amination reaction of a dipyrromethene ferrous complex with organic azides. Monitoring of the spectral changes (variable-temperature NMR and UV-vis) of the Fe(II) complex reveals no buildup of an intermediate during conversion of the starting material into the nitrene-inserted product. The rate-determining step appears to be azide addition to the 14-electron Fe(II) complex, hinting at the potential that these and related platforms may have to effect atom- and group-transfer processes.