Native Amino Group Directed Site-Selective ε-C(sp 2 )-H Iodination of Primary Amines.

Selective remote C-H activating amines using unmodified NH 2 as a native directing group demonstrate compelling synthetic utilities. The 3-arylpropan-1-amine moiety is present in many drugs and candidates in clinical trials. Selective iodination of 3-arylpropan-1-amines on remote aryl rings gives valuable intermediates for modifying bioactive molecules and synthesizing quinolones. Here we report the first palladium-catalyzed selective ε-C(sp 2 )-H iodination of free 3-arylpropan-1-amines via a seven-membered palladacycle.