Nucleophilic Reactions Using Alkali Metal Fluorides Activated by Crown Ethers and Derivatives

We review crown ether-facilitated nucleophilic reactions using metal salts, presenting the studies using kinetic measurements and quantum chemical methods. We focus on the mechanistic features, specifically on the contact ion-pair (CIP) mechanism of metal salts for nucleophilic processes promoted by crown ethers and derivatives. Experimental verification of the CIP form of the metal salt CsF complexed with [18-Crown-6] by H-NMR spectroscopy is described. The use of chiral crown ethers and derivatives for enantioselective nucleophilic processes is also discussed.

Automated summary

In this article, we review the studies on crown ether-facilitated nucleophilic reactions using metal salts, with a focus on the mechanistic features and experimental verification of the contact ion-pair (CIP) mechanism of metal salts. Kinetic measurements and quantum chemical methods are employed for the analysis. The use of chiral crown ethers and derivatives for enantioselective nucleophilic processes is also discussed.