Fluorinative ring-opening of cyclopropanes by hypervalent iodine reagents. An efficient method for 1,3-oxyfluorination and 1,3-difluorination† †Electronic supplementary information (ESI) available: Experimental procedures, characterization and NMR spectra of the products. See DOI: 10.1039/c6sc03471c Click here for additional data file.

Fluorinated organic compounds have found broad application in the pharmaceutical, and agrochemical industries as well as in medical diagnostics. The impetus for the application of organouorine compounds in agrochemical and pharmaceutical products is their benecial pharmacokinetic properties, such as high metabolic stability and lipophilicity. The useful radionuclear properties of the unnatural isotope F makes F labelled organouoro compounds indispensable for positron emission tomography (PET). The short half-life of F requires development of a rapid late stage introduction of the uorine atom, which is a challenging task in synthetic organic chemistry. In the last decade, many new uorinating reagents have appeared, which in combination of catalysts allowed development of new selective methodologies to access a broad variety of bioactive organouorines. Themost efficient methods are even suitable for uorination based difunctionalization reactions. The most studied approach involves vicinal difunctionalization reactions, such as 1,2-oxyuorination, 1,2-aminouorination, 1,2-carbouorination and related methods. Recently a number of interesting geminal uorination methods were also reported, such as 1,1-diuorination, 1,1-oxyuorination and 1,1-aminouorination. The 1,2-difunctionalization methods are usually based on alkene substrates, while the 1,1-difunctionalizations are oen realized using diazo compounds, as substrates. However, the analogue methodology is much less developed for 1,3-difunctionalization based uorination methods. Considering the typical synthetic methodologies for 1,3-difunctionalization reactions, a related uorination reaction can probably be achieved by ring opening of cyclopropane substrates. Recently, we have shown that hypervalent iodine based benziodoxol(on) derivatives are excellent reagents for