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Palladium-catalyzed activation of E-E and C-E bonds in diaryl dichalcogenides (E = S, Se) under microwave irradiation conditions Full article

Journal Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285
Output data Year: 2005, Volume: 54, Number: 3, Pages: 576-587 Pages count : 12 DOI: 10.1007/s11172-005-0292-6
Authors Ananikov V.P. 1 , Orlov N.V. 1 , Beletskaya I.P. 2
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2 Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation

Abstract: The first example of palladium-catalyzed stereoselective addition of diphenyl disulfide and diphenyl diselenide to the triple bond of terminal alkynes under microwave irradiation conditions is described. It was found that both the element—element (E-E) and carbon—element bonds can be activated in the catalytic system studied. The products of both reactions were isolated in quantitative yields. According to quantum-chemical calculations, the reaction mechanism involves the oxidative addition of the E-E bond to Pd0. Depending on the microwave power and reaction conditions, the next stage is either the reaction with alkyne or the carbon—element bond activation. The product of the oxidative addition of Ph2Se2 to Pd0, namely, dinuclear complex [Pd2(SePh)4(PPh3 2], was detected by 31P{1H}NMR spectroscopy directly in the Ph2Se2/PPh3 melt formed under microwave irradiation conditions.
Cite: Ananikov V.P. , Orlov N.V. , Beletskaya I.P.
Palladium-catalyzed activation of E-E and C-E bonds in diaryl dichalcogenides (E = S, Se) under microwave irradiation conditions
Russian Chemical Bulletin. 2005. V.54. N3. P.576-587. DOI: 10.1007/s11172-005-0292-6 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000232042300008
Scopus: 2-s2.0-25144461620
OpenAlex: W2953389475
Citing:
DB Citing
OpenAlex 36
Scopus 37
Web of science 37
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