Palladium and platinum catalyzed hydroselenation of alkynes: SeH vs SeSe addition to CC bond |
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Authors: | Valentine P Ananikov Denis A Malyshev Grigory G Aleksandrov |
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Affiliation: | a Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia b Department of Chemistry, Lomonosov Moscow State University, Vorob'evy gory, Moscow 119899, Russia c Kurnakov Institute of General and Inorganic Chemistry, Leninsky Prospect 31, Moscow 117907, Russia |
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Abstract: | A mechanistic study of the hydroselenation of alkynes catalyzed by Pd(PPh3)4 and Pt(PPh3)4 has shown that the palladium complex gives products of both SeH and SeSe bond addition to the triple bond of alkynes, while the platinum complex selectively catalyzes SeH bond addition. The key intermediate of PhSeH addition to the metal center, namely Pt(H)(SePh)(PPh3)2, was detected by 1H-NMR spectroscopy. The analogous palladium complex rapidly decomposes with evolution of molecular hydrogen. A convenient method was developed for the preparation of Markovnikov hydroselenation products H2CC(SePh)R, and the scope of this reaction was investigated. The first X-ray structure of the Markovnikov product H2CC(SePh)CH2N+HMe2·HOOCCOO− is reported. |
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Keywords: | Hydroselenation Vinyl selenide Platinum complex Palladium complex Catalytic reaction 77Se-NMR |
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