Synthesis of Diaryl Ethers, Diaryl Sulfides, Heteroaryl Ethers and Heteroaryl Sulfides under Microwave Dielectric Heating

Abstract

This paper describes the synthesis of diaryl ethers and sulfides by utilizing microwave heating methodology. The methodology is shown to be rapid and efficient for the coupling of phenols or thiophenol with electron-deficient aryl halides through a S_NAr reaction. The scope of the protocol can be expanded to six-membered heterocycles bearing a hydroxyl group as well as to the reaction of 2-pyrimidinethiol with mildly activated aryl halides, providing heteroaryl ethers and sulfides, respectively. The advantages of the present method include the wide substrate scope, the obviation of metal catalysts, ease of product isolation, and high purity of products.

Key words

dielectric heating - diaryl ether - diaryl sulfide - synthesis

References

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19

Under the usual refluxing acetonitrile conditions the same reaction catalyzed by potassium fluoride-alumina and 18-crown-6 occurred in 83% yield in 120 hours.⁶