Iodine-PEG As a Unique Combination for the Metal-free Synthesis of Flavonoids Through Iodonium-triiodide Ion-pair Complexation

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2024 Feb 20

PMID 38375003

Authors

Naveen Kumar

Navneet Sharma

Vijay Kumar

Vinay Kumar

Kailash Jangid

Bharti Devi

Ashish Ranjan Dwivedi

Kousik Giri

Rakesh Kumar

Vinod Kumar

Affiliations

Soon will be listed here.

Abstract

An efficient metal-free single-step protocol has been developed for the direct synthesis of flavones from 2-hydroxyacetophenone and substituted benzaldehydes. This chemical transformation is exclusively promoted by the iodonium-triiodide ion couple formed through iodine and PEG-400 complexation. The triiodide anion not only helps in the abstraction of a proton from the acetophenone but also promotes the cyclization of intermediate chalcone to the corresponding flavones. The flavones were obtained in very high yields without using any toxic metal catalysts or harsh reaction conditions. The reaction mechanism was established through a series of test reactions and entrapping of reaction intermediates. The developed protocol provides direct access to flavones in high yields under milder reaction conditions with great substrate compatibility, including hydroxylated derivatives.

Citing Articles

Mannich reaction mediated derivatization of chromones and their biological evaluations as putative multipotent ligands for the treatment of Alzheimer's disease.

Kumar N, Jangid K, Kumar V, Devi B, Arora T, Mishra J RSC Med Chem. 2024; .

PMID: 39399311 PMC: 11462584. DOI: 10.1039/d4md00550c.

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