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Structural effects of the carboxylate anion on Ru-catalyzed C—H arylation of (hetero)aromatic substrates containing N-donor directing group

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Abstract

Anions of carboxylic acids are widely used as the promoters of ruthenium-catalyzed reactions of C—H activation of substrates containing an N-donar directing group. The promoting effect of structure of anions of aliphatic and (hetero)aromatic carboxylic acids on the C—H arylation of benzene, furan, and thiophene rings in benzo[d]imidazol-2-yl-(hetero)arenes, wherein the benzimidazole moiety played the role of N-donor directing group, was evaluated. It was found that the structural effect of carboxylate anion on the efficiency of promotion of the catalytic system can significantly vary upon the arylation of different substrates. Adamantane-1-carboxylic acid was proposed as the most effective and universal promoter, based on which a new efficient catalytic system was developed for the selective arylation of benzo[d]imidazol-2-yl-(hetero)arenes.

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Acknowledgements

The authors are grateful to the Academician of the Russian Academy of Sciences V.P. Ananikov for a fruitful discussion of the results reported herein and valuable comments. The authors are thankful to the Center for Shared Use “Nanotechnologies” at the M. I. Platov South-Russian State Polytechnic University and the Center for Shared Use at the N. D. Zelinski Institute of Organic Chemistry of the Russian Academy of Sciences for carrying out analytical experiments.

Funding

This work was financially supported by the Russian Science Foundation (Project No. 21-73-00058).

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Authors and Affiliations

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

    I. G. Gnatiuk, K. A. Nikolaeva, K. E. Shepelenko & V. M. Chernyshev

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  1. I. G. Gnatiuk
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  2. K. A. Nikolaeva
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  3. K. E. Shepelenko
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  4. V. M. Chernyshev
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Correspondence to K. E. Shepelenko or V. M. Chernyshev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 3, pp. 497–504, March, 2024.

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Gnatiuk, I.G., Nikolaeva, K.A., Shepelenko, K.E. et al. Structural effects of the carboxylate anion on Ru-catalyzed C—H arylation of (hetero)aromatic substrates containing N-donor directing group. Russ Chem Bull 73, 497–504 (2024). https://doi.org/10.1007/s11172-024-4158-1

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