Palladium-catalyzed activation of E-E and C-E bonds in diaryl dichalcogenides (E = S,Se) under microwave irradiation conditions |
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Authors: | V P Ananikov N V Orlov I P Beletskaya |
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Institution: | (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 |
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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.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 569–580, March, 2005. |
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Keywords: | palladium complexes catalysis microwave irradiation diaryl dichalcogenides element— element bond activation carbon— element bond activation alkynes vinyl sulfides vinyl selenides quantum chemical calculations |
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