Iodination of remote ortho-C-H bonds of arenes via directed S _EAr: A streamlined synthesis of tetrahydroquinolines

摘要

A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed γ-C(sp~3)-H arylation, metal-free ε-C(sp~2)-H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.