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Catalytic C(sp2)–C(sp3) Cross-Electrophile Coupling in the PtII–NaI–С2Н3I–СН3I–Acetone System

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Abstract

A new catalytic system for reductive С(sp2)–C(sp3) cross-electrophile coupling was designed: PtII iodide complexes in an acetone solution of NaI catalyze the coupling of methyl iodide with vinyl iodide to form propylene. Simultaneously, a small amount of 1,3-butadiene, the product of C(sp2)–C(sp2) coupling, is released. The total yield of the products with respect to the reacted vinyl iodide is almost quantitative. In a large excess of CH3I, the C2H3I consumption is described by the pseudo-first-order kinetics. The cross-coupling occurs as the following sequence of steps: oxidative addition of CH3I to PtII iodide complexes to form a methyl PtIV complex → reduction of the methyl PtIV complex with I– to form the corresponding PtII derivative → oxidative addition of C2H3I to the PtII derivative → reductive elimination of organyl ligands from the intermediate methyl vinyl PtIV complex.

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Notes

  1. The product of the C(sp2)–C(sp2) coupling of butadiene was identified previously [18].

  2. The reversibility of the oxidative addition of methyl iodide to platinum(II) iodide complexes was shown previously [27, 28].

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Funding

This work was supported by the Ministry of Science and Higher Education of the Russian Federation, budget topic “Catalytic Transformations of Hydrocarbons and Their Derivatives under Homogeneous and Heterogeneous Conditions with the Formation of New C–C, S–O, and C–Element Bonds (FRES-2023-0005).”

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Authors and Affiliations

  1. Litvinenko Institute of Physical Organic Chemistry and Coal Chemistry, 283048, Donetsk, Russia

    T. V. Krasnyakova, D. V. Nikitenko & S. A. Mitchenko

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  1. T. V. Krasnyakova
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  2. D. V. Nikitenko
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  3. S. A. Mitchenko
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Correspondence to T. V. Krasnyakova.

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Translated by V. Glyanchenko

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Krasnyakova, T.V., Nikitenko, D.V. & Mitchenko, S.A. Catalytic C(sp2)–C(sp3) Cross-Electrophile Coupling in the PtII–NaI–С2Н3I–СН3I–Acetone System. Kinet Catal 65, 30–39 (2024). https://doi.org/10.1134/S002315842401004X

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