Cross-coupling of 4,5,6,7-tetrahydroindole with functionalized haloacetylenes on active surfaces of metal oxides and salts

Screening was performed of metal oxides (MgO, CaO, ZnO, BaO, Al₂O₃, TiO₂, ZrO₂) and salts (CaCO₃, K₂CO₃, ZrSiO₄) as active surfaces for the reaction of ethynylation of 4,5,6,7-tetrahydroindole with ethyl bromopropynoate and bromobenzoylacetylene. It was established that Ca, Mg, Zn, and Ba oxides ass...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2010-09, Vol.46 (9), p.1373-1377
Main Authors: Sobenina, L. N, Tomilin, D. N, Petrova, O. V, Gulia, N, Osowska, K, Szafert, S, Mikhaleva, A. I, Trofimov, B. A
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Screening was performed of metal oxides (MgO, CaO, ZnO, BaO, Al₂O₃, TiO₂, ZrO₂) and salts (CaCO₃, K₂CO₃, ZrSiO₄) as active surfaces for the reaction of ethynylation of 4,5,6,7-tetrahydroindole with ethyl bromopropynoate and bromobenzoylacetylene. It was established that Ca, Mg, Zn, and Ba oxides assist the ethynylation of 4,5,6,7-tetrahydroindole, and their activity in the reaction with ethyl bromopropynoate considerably exceeds that of aluminum oxide. The ethynylation is accompanied with the formation of intermediate E-2-(1-bromoethenyl)-4,5,6,7-tetrahydroindole and side 1,1-di(4,5,6,7-tetrahydroindol-2-yl)ethenes and 1,1-di(4,5,6,7-tetrahydroindol-2-yl)bromoethanes.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428010090186