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Related Experiment Video

Updated: Feb 25, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

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C-H Activation from Iron(II)-Nitroxido Complexes.

Claudia Kleinlein¹, Andrew J Bendelsmith¹, Shao-Liang Zheng¹

¹Department of Chemistry & Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA, 02138, USA.

Angewandte Chemie (International Ed. in English)

|August 3, 2017

Summary

Iron(II)-nitroxido complexes with TEMPO and AZADO radicals are synthesized. These complexes decompose via N-O bond homolysis in the presence of C-H bonds, forming iron hydroxides through hydrogen atom transfer.

Keywords:

C−H activation dipyrrin ligand hydrogen atom abstraction iron complexes nitroxyl radical

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Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

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Published on: March 19, 2020

Area of Science:

Organometallic Chemistry
Coordination Chemistry
Radical Chemistry

Background:

Nitroxyl radicals are versatile ligands in coordination chemistry.
Iron complexes with radical ligands offer unique reactivity pathways.
Understanding the stability and reactivity of iron-nitroxido complexes is crucial for catalytic applications.

Purpose of the Study:

To synthesize and characterize novel iron(II)-nitroxido complexes using TEMPO and AZADO radicals.
To investigate the reactivity of these complexes, particularly their decomposition pathways in the presence of C-H bonds.
To elucidate the mechanism of hydrogen atom transfer from C-H bonds to the iron-nitroxido species.

Main Methods:

Synthesis of iron(II)-nitroxido complexes with TEMPO and AZADO using an iron(I) synthon.
Spectroscopic characterization of the resulting complexes.
Reactivity studies involving 1,4-cyclohexadiene as a C-H bond source.
Mechanistic investigations including kinetic experiments to determine rate-determining steps.

Main Results:

Formation of stable high-spin iron(II)-nitroxido complexes: (Ar L)Fe(κ1-TEMPO) and (Ar L)Fe(κ2-N,O-AZADO).
Decomposition of complexes via N-O bond homolysis in the presence of 1,4-cyclohexadiene, yielding ferrous or ferric iron hydroxides.
(Ar L)Fe(κ1-TEMPO) forms a diferrous hydroxide, while (Ar L)Fe(κ2-N,O-AZADO) yields a ferric hydroxide.
Kinetic studies indicate saturation behavior and rate-determining hydrogen atom transfer.

Conclusions:

Iron(II)-nitroxido complexes exhibit distinct reactivity patterns based on the nitroxyl ligand.
The decomposition mechanism involves rate-determining hydrogen atom transfer from C-H bonds.
These findings provide insights into the fundamental reactivity of iron-radical systems and their potential in C-H activation processes.