4 years ago

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

Palladium-Catalyzed Remote meta-Selective C–H Bond Silylation and Germanylation
Debabrata Maiti, Rajdip Chowdhury, Atanu Modak, Tuhin Patra, Suman Raul
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.

Publisher URL: http://dx.doi.org/10.1021/acs.organomet.7b00309

DOI: 10.1021/acs.organomet.7b00309

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