Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp³)-H Bonds with Zhdankin's λ³-Azidoiodane.

ABSTRACT: An in-depth study of the mechanism of the azidation of C(sp³)-H bonds with Zhdankin's λ³-azidoiodane reagent catalyzed by iron(II)(pybox) complexes is reported. Previously, it was shown that tertiary and benzylic C(sp³)-H bonds of a range of complex molecules underwent highly site-selective azidation by reaction with a λ³-azidoiodane reagent and an iron(II)(pybox) catalyst under mild conditions. However, the mechanism of this reaction was unclear. Here, a series of mechanistic experiments are presented that reveal critical features responsible for the high selectivity and broad scope of this reaction. These experiments demonstrate the ability of the λ³-azidoiodane reagent to undergo I-N bond homolysis under mild condition

SUBMITTER: Day CS 

PROVIDER: S-EPMC8594407 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature