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

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

Journal

Journal of Organometallic Chemistry
ISSN: 1872-8561 , E-ISSN: 0022-328X

Output data

Year: 2003, Volume: 679, Number: 2, Pages: 162-172 Pages count : 11 DOI: 10.1016/s0022-328x(03)00546-1

Authors

Ananikov Valentine P ¹ , Malyshev Denis A ¹ , Beletskaya Irina P ² , Aleksandrov Grigory G ³ , Eremenko Igor L ³

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia
2	Department of Chemistry, Lomonosov Moscow State University, Vorob'evy gory, Moscow 119899, Russia
3	Kurnakov Institute of General and Inorganic Chemistry, Leninsky Prospect 31, Moscow 117907, Russia

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. Palladium catalyzed hydroselenation of alkynes gives the products of both SeH and SeSe bonds addition to the triple bond, while platinum complex selectively catalyzes SeH bond addition.

Ananikov V.P. , Malyshev D.A. , Beletskaya I.P. , Aleksandrov G.G. , Eremenko I.L.
Palladium and platinum catalyzed hydroselenation of alkynes: SeH vs SeSe addition to CC bond
Journal of Organometallic Chemistry. 2003. V.679. N2. P.162-172. DOI: 10.1016/s0022-328x(03)00546-1 Scopus OpenAlex

Scopus:	2-s2.0-0042531719
OpenAlex:	W2020456487

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