Dual C–F/C–H functionalization unveiled

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In an effort to develop a general method for making multifluorinated biaryl compounds, a pair of chemists has achieved the first example of a direct cross-coupling reaction between a C–F bond of one aryl compound and a C–H bond of another aryl compound without having to first prefunctionalize either of the aryl coupling partners like in traditional cross-coupling strategies (J. Am. Chem. Soc. 2016, DOI: 10.1021/jacs.5b13450). Sameera Senaweera and Jimmie D. Weaver of Oklahoma State University, Stillwater, previously determined how to use an iridium photocatalyst with amine reductant to selectively functionalize a C–F bond of multifluorinated aryl compounds. Along the way they realized there was an opportunity to go further with the perfluoroaryl radical intermediate and use it to couple with a nonfluorinated aryl partner if they could create the right reaction conditions. Starting from pentafluoropyridine, they found that the iridium catalyst with a bulky amine under blue LED light