Organo-catalyzed C2,3–H aminochalcogenation of indoles with secondary (aliphatic) amines†

Catalysis by small organic molecules capable of binding and activating substrates through attractive, non-covalent interactions has emerged as a highly significant approach in the fields of organic and organometallic chemistry. Notably, the utilization of organo-chalconium catalysts has gained substantial attention, owing to their remarkable catalytic properties, within the realms of synthetic chemistry and small molecule catalysis. In this study, we present a direct C2,3–H difunctionalization of indoles with unactivated amines (secondary aliphatic amines, more than 66 examples, up to 95% isolated yield), facilitated by the organo-chalconium catalyst generated through the reaction of iodine and chalconium reagents. This exceptional strategy not only provides a formidable tool for the assembly of intricate molecular architectures, but also affords the ability to perform late-stage functionalization of natural products and pharmaceutical compounds. Moreover, this advancement imparts unparalleled potential for optimizing the bioactivity and pharmacokinetic properties of existing drugs.