Russian Journal of Organic Chemistry

, Volume 38, Issue 10, pp 1475–1478 | Cite as

Mechanism of Catalytic Addition of Benzeneselenol to Alkynes

  • V. P. Ananikov
  • D. A. Malyshev
  • I. P. Beletskaya


Addition of benzeneselenol to terminal alkynes HCÍÄCR, catalyzed by Pd(0) complexes, leads to formation of mixtures of mono- and bis(phenylseleno)alkenes, depending on the nature of the R substituent. Electron-donor groups (R = Bu, CH2OH, CH2NMe2) give rise to addition according to the Markownikoff rule, whereas from alkynes with electron-acceptor groups (R = Ph, COOMe) mixtures of products are formed as a result of side reactions. A probable reaction mechanism includes oxidative addition of benzeneselenol to the metal, alkyne insertion into the PdÄSe bond, and reductive elimination.


Organic Chemistry Alkene Alkyne Reaction Mechanism Side Reaction 
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Copyright information

© MAIK “Nauka/Interperiodica” 2002

Authors and Affiliations

  • V. P. Ananikov
    • 1
  • D. A. Malyshev
    • 1
  • I. P. Beletskaya
    • 2
  1. 1.Zelinskii Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia
  2. 2.Faculty of ChemistryMoscow State UniversityVorob'evy gory, MoscowRussia

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