Palladium-Catalyzed Remote <i>meta</i>-Selective C–H Bond Silylation and Germanylation

Abstract

Selective meta-C–H activation of arenes to date has met with a limited number of functionalizations. Expanding the horizon of meta-C–H functionalization, herein we disclose an unprecedented meta-silylation and -germanylation protocol by employing a simple nitrile-based directing template. Longer linkers between the target site and the directing template were successfully explored for meta-silylation (sp2-ε and sp2-ζ). Additionally, synthetic utility was demonstrated with several postsynthetic elaborations and with a formal synthesis of TAC101, a promising drug for the treatment of lung cancer.