ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

An efficient three-component approach for the diastereoselective synthesis of trans-2,3-dihydrofuran derivatives: an exceptional catalytic activity of SiO₂ nanoparticles

Omekolsoom Sheibani and Sayed Hossein Banitaba

Department of Chemistry, Payame Noor University (PNU), Tehran, Iran

E-mail: h.banitaba@pnu.ac.ir

Received: 8 September 2021  Accepted: 13 January 2023

Abstract:

The performing organic reactions in the presence of solid nano-catalysts have attracted significant research interest in recent years. In this regard, a fast and operationally facile one-step tandem strategy for the diastereoselective synthesis of rel-(2R,3R)-2-benzoyl-2,3-dihydro-3-substitutedphenyl-4H-furo[3,2-c][1]benzopyran-4-one has been developed. This protocol has been applied via solvent-free condensation of aromatic aldehydes, 4-hydroxycoumarin, and in situ generated phenacyl pyridinium bromide over SiO₂ nanoparticles as a non-metal oxide catalyst. The protocol is environmentally favorable because the organic solvent is not required in the reaction process. Additionally, the method is rapid, has high yields, low catalyst loading and also does not involve extensive workup procedures or chromatographic separations. The catalyst is inexpensive and very mild and also is recyclable in six runs without losing activity significantly.

Keywords: Tandem reaction; Trans-2,3-dihydrofurans; Stereoselectivity; Pyridinium ylide; One-pot process; SiO2 nanoparticles

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-02822-3

Chemical Papers 77 (9) 4831–4841 (2023)