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CuI-catalyzed N,N’-diarylation of diamines of adamantane series

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Abstract

A copper(I) complex-catalyzed N,N’-diarylation of diamines based on 1,3-disubstituted adamantane, using aryl iodides bearing electron-donating and electron-withdrawing substituents, was studied. In the case of 2,2’-(adamantane-1,3-diyl)ethanediamine, the optimal catalyst system is CuI—2-(isobutyryl)cyclohexanone—Cs2CO3—DMF. The highest yield of diarylation product was reached in the case of 4-methoxyiodobenzene (79%). In the case of more spatially hindered adamantane-1,3-diyldimethanamine, 1,1’-binaphthalene-2,2’-diol (BINOL) should be used, with the highest yield of the target product (84%) being reached in the reaction with iodobenzene.

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    S. P. Panchenko, A. C. Abel, A. D. Averin, O. A. Maloshitskaya & I. P. Beletskaya

  2. Volgograd State Technical University, 28 prosp. Lenina, 400131, Volgograd, Russian Federation

    E. N. Savelyev, B. S. Orlinson & I. A. Novakov

Authors
  1. S. P. Panchenko
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  2. A. C. Abel
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  3. A. D. Averin
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  4. O. A. Maloshitskaya
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  5. E. N. Savelyev
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  6. B. S. Orlinson
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  7. I. A. Novakov
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  8. I. P. Beletskaya
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Corresponding author

Correspondence to A. D. Averin.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1550—1555, June, 2016.

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Panchenko, S.P., Abel, A.C., Averin, A.D. et al. CuI-catalyzed N,N’-diarylation of diamines of adamantane series. Russ Chem Bull 65, 1550–1555 (2016). https://doi.org/10.1007/s11172-016-1481-1

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  • DOI: https://doi.org/10.1007/s11172-016-1481-1

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