Mechanochemical Aliphatic Iodination (and Bromination) by Cascaded Cyclization

Aliphatic iodination via mechanochemistry is a mammoth challenge due to the high polarizability and weak electrophilicity of iodonium cation (I+), and low bond dissociation energy of carbon iodine bond. Herein, the synthesis is demonstrated of oxazoline derivatives from N-allyl benzamides via mechanochemical cascaded cyclization and halogenation using N-iodo- and N-bromosuccinimides, respectively, as bifunctional reagents.

Automated summary

In this study, oxazoline derivatives were successfully synthesized from N-allyl benzamides through a mechanochemical cascaded cyclization and halogenation using N-iodo- and N-bromosuccinimides as bifunctional reagents.