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Synthesis 2014; 46(18): 2489-2498
DOI: 10.1055/s-0034-1378206
DOI: 10.1055/s-0034-1378206
paper
A Solvent-Free and One-Pot Strategy for Ecocompatible Synthesis of Substituted Benzofurans from Various Salicylaldehydes, Secondary Amines, and Nonactivated Alkynes Catalyzed by Copper(I) Oxide Nanoparticles
Further Information
Publication History
Received: 03 March 2014
Accepted after revision: 12 May 2014
Publication Date:
25 June 2014 (online)
Abstract
Copper(I) oxide nanoparticles (CONPs) catalyze multicomponent coupling/cycloisomerization reactions between various 2-hydroxybenzaldehydes, secondary amines, and nonactivated alkynes to give 2,3-disubstituted 1-benzofurans. All reactions are carried out under solvent- and ligand-free conditions at 100 °C in air. The combination of copper-catalyzed C–H activation and an O-annulation process is essential for this transformation. This methodology provides rapid access to substituted 1-benzofurans in good to excellent yields with high atom economy and high catalytic efficiency. This procedure eliminates the need for propargylamine derivatives, uncyclized intermediates that make purification difficult. The CONPs and tetrabutylammonium bromide were reused successfully for up to five times.
Key words
1-benzofurans - copper(I) oxide nanoparticles - one-pot cascade reaction - solvent-free conditions - morpholineSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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