Issue 18, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
23 May 2017
Accepted
27 Jul 2017
First published
01 Aug 2017

New J. Chem., 2017,41, 9884-9888

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, 41, 9884 DOI: 10.1039/C7NJ01803G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements