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

Hashem Sharghi; Pezhman Shiri; Mahdi Aberi

doi:10.1055/s-0034-1378206

Synthesis, Table of Contents

Synthesis 2014; 46(18): 2489-2498
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

Hashem Sharghi*

Department of Chemistry, Shiraz University, Shiraz, 71454, Iran Fax: +98(711)2280926 Email: shashem@chem.susc.ac.ir

,

Pezhman Shiri

Department of Chemistry, Shiraz University, Shiraz, 71454, Iran Fax: +98(711)2280926 Email: shashem@chem.susc.ac.ir

,

Mahdi Aberi

Department of Chemistry, Shiraz University, Shiraz, 71454, Iran Fax: +98(711)2280926 Email: shashem@chem.susc.ac.ir

› Author Affiliations

Abstract

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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 - morpholine

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References

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Supplementary Material

Supporting Information

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

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