V. Ananikov, D. Malyshev, I. Beletskaya
Oct 1, 2002
Citations
0
Influential Citations
7
Citations
Journal
Russian Journal of Organic Chemistry
Abstract
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.