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

被引：19

作者：

Nozawa-Kumada, Kanako ^{[1
]}

Osawa, Sayuri ^{[1
]}

Sasaki, Midori ^{[1
]}

Chataigner, Isabelle ^{[2
]}

Shigeno, Masanori ^{[1
]}

Kondo, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, 6-3 Aoba, Sendai, Miyagi 9808578, Japan

[2] Normandie Univ, UNIROUEN, COBRA, INSA Rouen,CNRS, F-76000 Rouen, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 18期

基金：

日本学术振兴会;

关键词：

PALLADIUM-CATALYZED SILYLATION; RUPPERT-PRAKASH REAGENT; POTASSIUM TERT-BUTOXIDE; CROSS-COUPLING REACTION; ONIUM AMIDE BASES; ARYL HALIDES; TERMINAL ALKYNES; FUNCTIONALIZATION; HETEROARENES; HYDROSILANES;

D O I：

10.1021/acs.joc.7b01525

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：9487 / 9496

页数：10

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