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Ytterbium(III)-catalyzed three-component reactions: synthesis of 4-organoselenium-quinolines

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Abstract

4-Organoselenium-quinolines were synthesized via model multi-component Povarov (MCR) reactions between p-anisidine, ethyl glyoxylate and ethynyl(phenyl)selane, catalyzed by the Lewis acid Yb(OTf)3, with yields ranging from moderate to good. This method is advantageous in that there is no requirement for an oxidant and that the reaction has a wide scope. These 4-organoselenium-quinolines allowed access to 4-alkynyl-quinolines, which were synthesized via copper free Sonogashira cross-coupling reactions catalyzed by a new palladium catalyst that employs an oxazoline derivative as a ligand. A plausible mechanism was proposed based on HRMS studies.

Graphical abstract: Ytterbium(iii)-catalyzed three-component reactions: synthesis of 4-organoselenium-quinolines

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Publication details

The article was received on 23 May 2017, accepted on 27 Jul 2017 and first published on 01 Aug 2017


Article type: Paper
DOI: 10.1039/C7NJ01803G
Citation: New J. Chem., 2017, Advance Article
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    Ytterbium(III)-catalyzed three-component reactions: synthesis of 4-organoselenium-quinolines

    I. M. de Oliveira, S. S. N. Vasconcelos, C. S. Barbeiro, T. C. Correra, A. Shamim, D. C. Pimenta, I. Caracelli, J. Zukerman-Schpector, H. A. Stefani and F. Manarin, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ01803G

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