Greener and Additive‐Free Ring Opening of Epoxides by All‐in‐One Choline Systems

Adaptation of all‐in‐one ionic systems with ionic liquids (ILs) serving as solvent, reactant, and catalyst is an innovative approach in the organic synthesis. Mild and bio clean choline based ILs as all‐in‐one systems (solvent, reagent, and catalyst) were developed via a simple metathesis approach a...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:ChemistrySelect (Weinheim) 2020-12, Vol.5 (46), p.14538-14542
Hauptverfasser: Shahiri‐Haghayegh, Mehran, Azizi, Najmedin, Heidarzadeh, Fatemeh
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Adaptation of all‐in‐one ionic systems with ionic liquids (ILs) serving as solvent, reactant, and catalyst is an innovative approach in the organic synthesis. Mild and bio clean choline based ILs as all‐in‐one systems (solvent, reagent, and catalyst) were developed via a simple metathesis approach and were applied on the ring‐opening reaction of epoxides. Sustained transformation of various epoxides using choline cyanide, azide, and hydroxide ILs delivered a neat, efficient and convenient protocol for the synthesis of β‐substituted alcohols in moderate to high yields (64‐97 %) with excellent activity and selectivity as confirmed by nuclear magnetic resonance (NMR) spectroscopic data. Effective ring‐opening of epoxides under additive‐free conditions with choline based ionic liquids as all‐in‐one systems. Eco‐friendly and cost‐effective choline based ILs were developed to sustain harsh reagents of cyanide, azide, and hydroxide. Efficient ring‐opening of structurally diverse epoxides afforded by the neat usage of the ILs, revealed the remarkable capacity of these materials as active media in synthetic chemistry where they provide the required nucleophilic species while simultaneously acting as a catalyst and a benign media (all‐in‐one ionic systems). The easy‐operation protocol developed herein enables moderate to high yields access to the desired β‐substituted alcohols (64–97 %) in excellent selectivity.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202002815