Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride

作者：Nozawa Kumada Kanako; Osawa Sayuri; Sasaki Midori; Chataigner Isabelle; Shigeno Masanori; Kondo Yoshinori^*

来源：Journal of Organic Chemistry, 2017, 82(18): 9487-9496.

DOI：10.1021/acs.joc.7b01525

A method for the deprotonative silylation of aromatic C-H bonds has been developed using trifluoromethyltrimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) and a catalytic amount of fluoride. In this reaction, CF3SiMe3 is considered to act as a base and a silicon electrophile. This process is highly tolerant to various functional groups on heteroarenes and benzenes. Furthermore, this method can be applied to the synthesis of trimethylsilyl group-containing analogs of TAC-101, which is a bioactive synthetic retinoid with selective affinity for retinoic acid receptor alpha (RAR-alpha) binding. We also report further transformations of the silylated products into useful derivatives.

• 出版日期2017-9-15