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Comparative activity of aryl, alkyl, and cycloalkyl halides in the suzuki reaction catalyzed with acyclic diaminocarbene complex of palladium

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Abstract

Relative activity of halogenated arenes, alkanes, and alkanes in the Suzuki reaction catalyzed with acyclic diaminocarbene complex of palladium has been investigated. Under all the investigated conditions, 4-iodoanisole has been more active than the alkyl halides. The reaction with 4-methyl-1-(chloromethyl)benzene has afforded the target 4-methyl-1-(phenylmethyl)benzene along with significant amount of by-products; other alkyl and cycloalkyl halides do not participate into the cross-coupling reaction. Ethanol has been found the most suitable solvent for the reaction. The reaction in acetonitrile provides noticeable yield of the products only in the presence of polyethylene glycol and water.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskaya nab. 7–9, St. Petersburg, 199034, Russia

    S. A. Kras’ko, S. S. Zlotskii & V. P. Boyarskii

  2. Ufa State Petroleum Technical University, Ufa, Russia

    S. A. Kras’ko

Authors
  1. S. A. Kras’ko
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  2. S. S. Zlotskii
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  3. V. P. Boyarskii
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Correspondence to V. P. Boyarskii.

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Original Russian Text © S.A. Kras’ko, S.S. Zlotskii, V.P. Boyarskii, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 11, pp. 1799–1804.

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Kras’ko, S.A., Zlotskii, S.S. & Boyarskii, V.P. Comparative activity of aryl, alkyl, and cycloalkyl halides in the suzuki reaction catalyzed with acyclic diaminocarbene complex of palladium. Russ J Gen Chem 85, 2541–2546 (2015). https://doi.org/10.1134/S1070363215110079

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  • DOI: https://doi.org/10.1134/S1070363215110079

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