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

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Abstract

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.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    L. N. Sobenina, D. N. Tomilin, O. V. Petrova, A. I. Mikhaleva & B. A. Trofimov

  2. University of Wroclaw, Wroclaw, Poland

    N. Gulia & K. Osowska

  3. Wroclaw Research Center EIT+ Ltd., Wroclaw, Poland

    S. Szafert

Authors
  1. L. N. Sobenina
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  2. D. N. Tomilin
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  3. O. V. Petrova
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  4. N. Gulia
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  5. K. Osowska
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  6. S. Szafert
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  7. A. I. Mikhaleva
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  8. B. A. Trofimov
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Corresponding author

Correspondence to B. A. Trofimov.

Additional information

Dedicated to Full Member of the Russian Academy of Sciences N.S. Zefirov on occasion of his 75th anniversary

Original Russian Text © L.N. Sobenina, D.N. Tomilin, O.V. Petrova, N. Gulia, K. Osowska, S. Szafert, A.I. Mikhaleva, B.A. Trofimov, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 9, pp. 1371–1375.

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Sobenina, L.N., Tomilin, D.N., Petrova, O.V. et al. Cross-coupling of 4,5,6,7-tetrahydroindole with functionalized haloacetylenes on active surfaces of metal oxides and salts. Russ J Org Chem 46, 1373–1377 (2010). https://doi.org/10.1134/S1070428010090186

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  • DOI: https://doi.org/10.1134/S1070428010090186

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