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Synthesis and Benzene Hydroxylation Properties of Amino Substituted [FeFe]-Hydrogenase Model Compounds

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Abstract

Two novel, amino-substituted [FeFe]-hydrogenase model compounds were synthesized and characterized using IR, NMR, mass and UV–Vis spectroscopies as well as elemental analysis. The electrochemical properties (cyclic voltammetry) and catalytic performances of compounds 1 and 2 for the hydroxylation of benzene were investigated. The reduction peaks of compounds 1 and 2 were observed at − 1.93 V, which agrees with the value of the electron density of diiron centers. Compounds 1 and 2 nearly the same electron density around the Fe–Fe bond, but the position of –NH2 group on the pyridine ring largely influenced the stability. Compound 1 demonstrated a higher phenol yield (equal to 12.8%) than compound 2 (10.2%). The biomimetic catalyst formed by the 4-aminopyridine ligand with two iron nuclei, resembling an enzyme active site, had better stability and higher catalytic activity than the 2-aminopyridine derivative.

Graphic Abstract

Compared the catalytic performance of complexes 1–2, despite 1 and 2 have the same electron density around the Fe–Fe bond, the 4-aminopyridine derivative 1 (12.8%) was more stable and with better catalytic activity compared to 2-aminopyridine derivative 2 (10.2%)

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Acknowledgements

The Natural Science Foundation of Shandong Province (ZR2019BF033 and ZR2019BB058); The Young Doctor Cooperative Foundation of Qilu University of Technology (Shandong Academy of Sciences) (81110361).

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Authors and Affiliations

  1. Advanced Research Institute for Multidisciplinary Science, Qilu University of Technology (Shandong Academy of Science), Jinan, 250353, Shandong, People’s Republic of China

    Xia Zhang & Lihong Liu

  2. The International School for Optoelectronic Engineering, Qilu University of Technology (Shandong Academy of Science), Jinan, 250353, Shandong, People’s Republic of China

    Lihong Liu

  3. School of Chemistry and Pharmaceutical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan, 250353, Shandong, People’s Republic of China

    Xia Zhang & Yingzhou Li

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  1. Xia Zhang
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  2. Lihong Liu
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Correspondence to Xia Zhang.

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Zhang, X., Liu, L. & Li, Y. Synthesis and Benzene Hydroxylation Properties of Amino Substituted [FeFe]-Hydrogenase Model Compounds. Catal Lett 150, 2879–2885 (2020). https://doi.org/10.1007/s10562-020-03197-w

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