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Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes

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Abstract

Palladium-catalyzed amination of isomeric bromochloro- and dibromobenzenes with 1- and 2-aminoadamantanes was studied. The best yields of the corresponding monoamination products were obtained in the reactions of 2-aminoadamantane with bromochlorobenzenes. The arylation of 1-aminoadamantane was successful in the presence of donor phosphine ligand. The amination of o- and m-dibromobenzenes was strongly complicated by formation of diamination products. Conditions ensuring predominant formation of the latter were found. The arylation of 2-aminoadamantane was accompanied by oxidation of the initial amine and reduction of aryl halide.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia

    A. D. Averin, M. A. Ulanovskaya, V. V. Kovalev & I. P. Beletskaya

  2. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Moscow, Russia

    A. K. Buryak

  3. Volgograd State Technical University, Volgograd, Russia

    B. S. Orlinson & I. A. Novakov

Authors
  1. A. D. Averin
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  2. M. A. Ulanovskaya
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  3. V. V. Kovalev
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  4. A. K. Buryak
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  5. B. S. Orlinson
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  6. I. A. Novakov
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  7. I. P. Beletskaya
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Correspondence to A. D. Averin.

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Original Russian Text © A.D. Averin, M.A. Ulanovskaya, V.V.Kovalev, A.K. Buryak, B.S. Orlinson, I.A. Novakov, I.P. Beletskaya, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 1, pp. 64–72.

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Averin, A.D., Ulanovskaya, M.A., Kovalev, V.V. et al. Palladium-catalyzed amination of isomeric dihalobenzenes with 1- and 2-aminoadamantanes. Russ J Org Chem 46, 64–72 (2010). https://doi.org/10.1134/S1070428010010069

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  • DOI: https://doi.org/10.1134/S1070428010010069

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