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Arylation of adamantanamines: III. Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine

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Abstract

Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl) diethanamine with isomeric bromochloro- and dibromobenzenes was studied. The yields of N,N′-diarylation products depend on the initial diamine and dihalobenzene structure. Side reactions were revealed, which reduced the yield of the target products. The arylation of 2,2′-(adamantane-1,3-diyl)diethanamine gives the corresponding N,N′-diaryl derivatives with better yield. The possibility for synthesizing unsymmetrical N,N′-diaryl derivatives of 2,2′-(adamantane-1,3-diyl)diethanamine was demonstrated.

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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 & 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

    E. N. Savel’ev, B. S. Orlinson & I. A. Novakov

Authors
  1. A. D. Averin
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  2. M. A. Ulanovskaya
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  3. A. K. Buryak
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  4. E. N. Savel’ev
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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.

Additional information

Original Russian Text © A.D. Averin, M.A. Ulanovskaya, A.K. Buryak, E.N. Savel’ev, B.S. Orlinson, I.A. Novakov, I. P. Beletskaya, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 1, pp. 35–44.

For communication II, see [1].

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Averin, A.D., Ulanovskaya, M.A., Buryak, A.K. et al. Arylation of adamantanamines: III. Palladium-catalyzed arylation of adamantane-1,3-diyldimethanamine and 2,2′-(adamantane-1,3-diyl)diethanamine. Russ J Org Chem 47, 30–40 (2011). https://doi.org/10.1134/S1070428011010027

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  • DOI: https://doi.org/10.1134/S1070428011010027

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