フッ素のユニークな使い方: フッ素（F2）を活性化剤として用いる有機合成化学反応

概要

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Fluorinated organic compounds have received increasing attention due to their unique biological nature in medicinal science and peerlessly excellent property in material science. And thus, a lot of methods for synthesizing highly functionalized fluorinated organic compounds and a number of suitably designed fluorinating reagents have been developed in recent years, most of which have been well documented in excellent reviews and books. However, no review on unique utilization of fluorine(F2) for functionalizing or synthesizing fluorine-free organic compounds has been published. This review involves the fluorine-promoted functionalizations such as oxidations of thiophenes to thiophene S,S-dioxides, pyridines and quinolines to the corresponding N-oxides, and amino group to nitro group along with direct hydroxylation and iodination of aromatics, epoxidation of electron-deficient alkenes, and direct functionalization of 2-position of pyridines. Almost instantaneous oxygen transfer reactions under mild conditions and effective generations of hydoxylium and iodonium ion equivalents otherwise impossible characterize the fluorine-promoted functionalizations.