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Stereoselective addition of aliphatic thiols to internal alkynes in a catalytic system with palladium “nanosalt” as an active site

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Abstract

An efficient catalytic system based on easily available palladium acetate was developed for the selective addition of aliphatic thiols to the triple bond of internal alkynes. Formed in situ [M(SR)2] n nanostructured particles were found to be an active form of the catalyst. It was experimentally confirmed for the first time that the most active form of the catalyst for thiol addition to internal alkynes is formed only in the reaction mixture containing the both reactants, namely, alkyne and thiol.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    N. V. Orlov, I. V. Chistyakov & V. P. Ananikov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    Z. A. Starikova

  3. Department of Chemistry, M. V. Lomonosov Moscow State University, 1/3 Leninskie gory, 119899, Moscow, Russian Federation

    I. P. Beletskaya

Authors
  1. N. V. Orlov
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  2. I. V. Chistyakov
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  3. Z. A. Starikova
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  4. V. P. Ananikov
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  5. I. P. Beletskaya
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Correspondence to V. P. Ananikov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0048–0055, January, 2013.

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Orlov, N.V., Chistyakov, I.V., Starikova, Z.A. et al. Stereoselective addition of aliphatic thiols to internal alkynes in a catalytic system with palladium “nanosalt” as an active site. Russ Chem Bull 62, 47–54 (2013). https://doi.org/10.1007/s11172-013-0007-3

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  • DOI: https://doi.org/10.1007/s11172-013-0007-3

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