Deaminative bromination, chlorination, and iodination of primary amines

The primary amino group has been seldom utilized as a transformable function-ality in organic synthesis. Reported herein is a deaminative halogenation of primary amines using N-anomeric amide as the nitrogen-deletion reagent. Both aliphatic and aromatic amines are competent substrates for direct halogenations. The mildness and robustness of the protocol are evidenced by the successful re-actions of several complex-and functional group-enriched bioactive compounds or drugs. Elaboration of the resulting products provides interesting analogues of drug molecules.

Automated summary

A deaminative halogenation method for primary amines using N-anomeric amide as the nitrogen-deletion reagent is reported in this article. The method is suitable for direct halogenation reactions of both aliphatic and aromatic amines, and has been successfully applied to various complex and functional group-enriched bioactive compounds or drugs. Elaboration of the resulting products provides interesting analogues of drug molecules.