Iridium- and Rhodium-Catalyzed Directed C–H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents

The C–H heteroarylation of benzaldehydes with indoles and pyrroles was realized using the benziodoxolone hypervalent iodine reagents indole- and pyrroleBX. Functionalization of the aldehyde C–H bond using either an o-hydroxy or amino directing group and catalyzed by an iridium or a rhodium complex allowed the synthesis of salicyloylindoles and (2-sulfonamino)­benzoylindoles, respectively, with good to excellent yields (74–98%). This new transformation could be carried out under mild conditions (rt to 40 °C) and tolerated a broad range of functionalities, such as ethers, halogens, carbonyls, or nitro groups.