Copper-Catalyzed Aminoheteroarylation of Unactivated Alkenes through Distal Heteroaryl Migration

We report a copper-catalyzed aminoheteroarylation of unactivated alkenes to access valuable heteroarylethylamine motif. The developed reaction features a copper-catalyzed intermolecular electrophilic amination of the alkenes followed by a migratory heteroarylation. The method applies to alcohol-, amide-, and ether-containing alkenes, overcoming the common requirement of a hydroxyl motif in previous migratory difunctionalization reactions. This reaction is effective for the introduction of diverse aliphatic amines and has good functional group tolerance, which is particularly useful for rich functionalized heteroarenes. This migration-involved reaction was found well suited as a powerful ring-expansion approach for the construction of medium-sized rings that are in great demand in medicinal chemistry.

Automated summary

A copper-catalyzed aminoheteroarylation of unactivated alkenes was developed for the synthesis of valuable heteroarylethylamine motif. This reaction is applicable to alkenes containing alcohol, amide, and ether groups, allowing for the introduction of diverse aliphatic amines. The migration-involved reaction serves as a powerful ring-expansion approach in medicinal chemistry.