Palladium and platinum catalyzed hydroselenation of alkynes: SeH vs SeSe addition to CC bond期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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Palladium and platinum catalyzed hydroselenation of alkynes: SeH vs SeSe addition to CC bond

Authors:	Valentine P Ananikov Denis A Malyshev Grigory G Aleksandrov

Institution:	^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

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 SeH and SeSe bond addition to the triple bond of alkynes, while the platinum complex selectively catalyzes SeH 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 H₂CC(SePh)R, and the scope of this reaction was investigated. The first X-ray structure of the Markovnikov product H₂CC(SePh)CH₂N⁺HMe₂·HOOCCOO⁻ is reported.

Keywords:	Hydroselenation Vinyl selenide Platinum complex Palladium complex Catalytic reaction ⁷⁷Se-NMR
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