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A study of the reactivity and transformations of Pd/NHC complexes in the reaction of oxidative C−H acetoxylation

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Abstract

A comparative study of the reactivity and transformation and degradation pathways under conditions of the oxidative acetoxylation was carried out for various palladium complexes. The implementation was confirmed for the NHC-connected mechanism of catalysis. Effects of the process of pyridine coligand elimination on catalysis were investigated. It was found that free pyridine inhibits the catalysis of oxidative acetoxylation of 2-phenylpyridine. Mono- and diacetoxyphenylpyridines were obtained regioselectively in 84–94% yields using Pd/NHC complexes of various structures.

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Funding

The authors are grateful to Prof. V. M. Chernyshev and the Academician of the Russian Academy of Sciences V. P. Ananikov for a fruitful discussion of the results reported herein and valuable comments, as well as to the Shared Research Center “Nanotechnologies” at the M. I. Platov South-Russian State Polytechnic University and the Shared Research Center at the N. D. Zelinskiy Institute of Organic Chemistry of the Russian Academy of Sciences for conducting analytical experiments.

This work was financially supported by the Russian Science Foundation (Project No. 19-73-10100).

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  1. M. I. Platov South-Russian State Polytechnic University, 132 ul. Prosveshcheniya, 346428, Novocherkassk, Russian Federation

    V. V. Chesnokov, M. A. Shevchenko & A. V. Astakhov

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  1. V. V. Chesnokov
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  2. M. A. Shevchenko
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  3. A. V. Astakhov
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Correspondence to A. V. Astakhov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1247–1256, June, 2022.

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Chesnokov, V.V., Shevchenko, M.A. & Astakhov, A.V. A study of the reactivity and transformations of Pd/NHC complexes in the reaction of oxidative C−H acetoxylation. Russ Chem Bull 71, 1247–1256 (2022). https://doi.org/10.1007/s11172-022-3526-y

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