Copper-Catalyzed Direct Perfluoroalkylation of Heteroarenes

An efficient and broadly applicable process is reported for the copper-catalyzed direct perfluoroalkylation of C-H bonds in heteroarenes with commercially available perfluoroalkyl iodides. This reaction is based on a simple combination of copper(I) iodide and 1,10-phenanthroline enabling the easy reduction of perfluoroalkyl iodides to the corresponding radical species that add to a wide range of heteroarenes including benzofurans, benzothiophenes, (aza)indoles, furans and pyrroles. High levels of regioselectivity were obtained in all cases and the efficiency and robustness of this process was highlighted by the direct perfluoroalkylation of furan-containing peptides.

Automated summary

This study presents an efficient process for the copper-catalyzed direct perfluoroalkylation of C-H bonds in heteroarenes using commercially available perfluoroalkyl iodides. The combination of copper(I) iodide and 1,10-phenanthroline enables the easy reduction of perfluoroalkyl iodides to radical species that add to a wide range of heteroarenes, showcasing high regioselectivity. The efficiency and robustness of this process is demonstrated by the direct perfluoroalkylation of furan-containing peptides.