Palladium-Catalyzed Remote meta-Selective C-H Bond Silylation and Germanylation

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 (sp(2)-epsilon and sp(2)-zeta). 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