Selectfluor as “Fluorine-Free” Functional Reagent Applied to Organic Synthesis under Transition Metal-Free Conditions

Abstract

Selectfluor, a commercial electrophilic fluorination reagent with superior performance, is widely used in fluorination reactions. In recent years, Selectfluor has also been widely applied as "fluorine-free" functional reagent in organic synthesis. Especially the application of Selectfluor/transition metals synergetic catalytic system has made great progress. However, this catalytic system has some disadvantages, such as the use of expensive transition metals and environmental unfriendliness. Therefore, more and more attention has been paid to the application of Selectfluor as "fluorine-free" functional reagent under transition metal-free conditions. In this paper, classified by the type of reactions, the research progress of Selectfluor as a "fluorine-free" functional reagent in organic synthesis under transition metal-free conditions is reviewed, and their future outlook is also discussed.

Selectfluor-Enabled C(sp3)–H Alkoxylation of 3-Methylfuranocoumarins

“…Undoubtedly, classic fluoroalkoxylation of the 3-methylfuran ring occurred in the presence of Selectfluor and alcohols (Scheme c) . In recent years, the application of Selectfluor as a “fluorine-mediated” functional reagent under transition-metal-free conditions was realized in organic synthesis. , 3-Methylfuranocoumarin is an important pharmaceutical intermediate, and in a continuation of our group’s work on fluorine chemistry and C–H activation, − we envisioned that 3-methylfuranocoumarin and alcohols might provide the C­(sp 3 )–H ethers using Selectfluor under metal-free conditions. Herein, we report our research results (Scheme d).…”