TY - JOUR
T1 - Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride
AU - Nozawa-Kumada, Kanako
AU - Osawa, Sayuri
AU - Sasaki, Midori
AU - Chataigner, Isabelle
AU - Shigeno, Masanori
AU - Kondo, Yoshinori
N1 - Funding Information:
This work was partly supported by “JSPS KAKENHI Grant Number 16H00997 in Precisely Designed Catalysts with Customized Scaffolding”, a Grant-in-Aid for Young Scientists (B) (No. 17K15418) from the Japan Society for the promotion of Science, and the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED).
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/9/15
Y1 - 2017/9/15
N2 - 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 α (RAR-α) binding. We also report further transformations of the silylated products into useful derivatives.
AB - 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 α (RAR-α) binding. We also report further transformations of the silylated products into useful derivatives.
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U2 - 10.1021/acs.joc.7b01525
DO - 10.1021/acs.joc.7b01525
M3 - Article
C2 - 28809110
AN - SCOPUS:85029509324
SN - 0022-3263
VL - 82
SP - 9487
EP - 9496
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -