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

共 50 条

[31] Efficient activation of aromatic C-H bonds for addition to C-C multiple bonds
Jia, CG
Piao, DG
Oyamada, JZ
Lu, WJ
Kitamura, T
Fujiwara, Y
SCIENCE, 2000, 287 (5460) : 1992 - 1995
[32] Rare-Earth-Catalyzed C-H Silylation of Aromatic Heterocycles with Hydrosilanes
Xu, Wenxuan
Teng, Huailong
Luo, Yong
Lou, Shaojie
Nishiura, Masayoshi
Hou, Zhaomin
CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (06) : 753 - 756
[33] Ruthenium-Catalyzed Dehydrogenative Aromatic C-H Silylation of Benzamides with Hydrosilanes
Takada, Kosuke
Hanataka, Tsurugi
Namikoshi, Takeshi
Watanabe, Shinji
Murata, Miki
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2229 - 2232
[34] Sequential Activation of Aromatic C-H Bonds on Cu(111)
Han, Dong
Tao, Zhijie
Wang, Tao
Feng, Lin
Li, Xingyu
Zeng, Zhiwen
Zhu, Junfa
JOURNAL OF PHYSICAL CHEMISTRY C, 2022, 126 (12): : 5541 - 5549
[35] Direct Amination of Aromatic C-H Bonds with Free Amines
Yang, Yafeng
Zhang, Dangquan
Vessally, Esmail
TOPICS IN CURRENT CHEMISTRY, 2020, 378 (02)
[36] Organoelectrophotocatalytic C-H Silylation of Heteroarenes
Wan, Qinhui
Hou, Zhong-Wei
Zhao, Xin-Ru
Xie, Xiaoyu
Wang, Lei
ORGANIC LETTERS, 2023, 25 (06) : 1008 - 1013
[37] Synthesis of Tetrasilatetrathia[8]circulenes by a Fourfold Intramolecular Dehydrogenative Silylation of C-H Bonds
Serizawa, Yuma
Akahori, Shuhei
Kato, Shohei
Sakai, Hayato
Hasobe, Taku
Miyake, Yoshihiro
Shinokubo, Hiroshi
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (29) : 6948 - 6952
[38] Emerging Strategies for C-H Silylation
Richter, Sven C.
Oestreich, Martin
TRENDS IN CHEMISTRY, 2020, 2 (01): : 13 - 27
[39] C-H Bond Silylation of Heteroarenes
Khatua, Hillol
Das, Subrata
Patra, Sima
Chattopadhyay, Buddhadeb
SYNTHESIS-STUTTGART, 2023, 55 (21): : 3434 - 3453
[40] ORGN 883-Palladium-catalyzed C-H activation/functionalization of aromatic C-H bonds
Kalyani, Dipannita
Dick, Allison R.
Deprez, Nick R.
Anani, Waseem Q.
Sanford, Melanie S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234

← 1 2 3 4 5 →