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Transition metal catalyzed Fe–C coupling reactions in synthesis of dicarbonyl(2-thienylethynyl)(η5-cyclopentadienyl)iron complex: Spectroscopic, structure and electrochemical study

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Abstract

The new σ-alkynyl iron(II) complex Cp(CO)2Fe-C≡C-(2-C4H3S) was synthesized with application of several known approaches based on the transition metal (Pd/Cu–, Au–, Cu– and Pd–) catalyzed Fe–C coupling reactions of 2-ethynylthiophene or 2-[(trimethylsilyl)ethynyl]thiophene with cyclopentadienyliron dicarbonyl iodide. The yield of the complex in these reactions was found to strongly depend on the catalyst used. The conditions, catalysts, and reagents that provide the highest yields of the desired 2-thienylethynyl iron complex were determined. The complex was characterized by IR, 1H and 13C NMR spectroscopy. The molecular structure of Cp(CO)2Fe–C≡C-(2-C4H3S) established by X-ray diffraction analysis exhibits a three-leg piano stool geometry. The redox properties of the new complex were studied.

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Notes

  1. Potentials are given versus Ag/0.1 M AgNO3 couple in MeCN (they can be converted to V versus SCE by adding 0.337 V).

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Acknowledgments

Physicochemical characteristics were obtained at the Krasnoyarsk Regional Centre of Research Equipment, Siberian Branch of the Russian Academy of Sciences.

Funding

This research was funded by a grant from the Russian Science Foundation (Project No. 18-73-00150).

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Authors and Affiliations

  1. Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”, Akademgorodok, 50-24, Krasnoyarsk, Russia, 660036

    Victor V. Verpekin, Ivan S. Ahremchik, Galina V. Burmakina, Alexander A. Kondrasenko & Tatyana S. Nedelina

  2. Institute of Physics SB RAS, Federal Research Center “Krasnoyarsk Science Center SB RAS”, Akademgorodok, 50-38, Krasnoyarsk, Russia, 660036

    Alexander D. Vasiliev

  3. Siberian Federal University, Svobodny prospekt, 79, Krasnoyarsk, Russia, 660041

    Ivan S. Ahremchik & Alexander D. Vasiliev

  4. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, Russian Federation, 119991

    Arkadii Z. Kreindlin

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  1. Victor V. Verpekin
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  2. Ivan S. Ahremchik
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Contributions

VVV: Conceptualization, Funding acquisition, Investigation, Methodology, Supervision, Writing. ISA: Investigation. ADV: X-ray diffractometry investigation. GVB: Electrochemical investigation. AAK: NMR investigation. TSN: Electrochemical investigation. AZK: investigation.

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Correspondence to Victor V. Verpekin.

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Verpekin, V.V., Ahremchik, I.S., Vasiliev, A.D. et al. Transition metal catalyzed Fe–C coupling reactions in synthesis of dicarbonyl(2-thienylethynyl)(η5-cyclopentadienyl)iron complex: Spectroscopic, structure and electrochemical study. Transit Met Chem 45, 589–594 (2020). https://doi.org/10.1007/s11243-020-00413-9

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