Deprotonative C-H Silylation of Functionalized Arenes and Heteroarenes Using Trifluoromethyltrialkylsilane with Fluoride

被引：29

作者：

Sasaki, Midori ^{[1
]}

Kondo, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 04期

基金：

日本学术振兴会;

关键词：

PALLADIUM-CATALYZED SILYLATION; CARBON-HYDROGEN BONDS; ONIUM AMIDE BASES; NUCLEOPHILIC TRIFLUOROMETHYLATION; ARYL HALIDES; SUBSTITUTED BENZENES; EFFICIENT PRECURSOR; PROTON ABSTRACTION; SYNTHETIC ROUTE; HYDROSILANES;

D O I：

10.1021/ol503671b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly selective C-H silylation reaction of functionalized arenes and heteroarenes was developed using RuppertPrakash reagent (TMSCF3) activated by alkali metal fluoride. TMSCF3 is considered to play dual roles as a precursor of a mild base and also as a silicon electrophile. The silylation is compatible with sensitive functional groups such as halogen and nitro groups.

引用

页码：848 / 851

页数：4

共 50 条

[31] A General Copper/Manganese Cocatalyzed C-H Selenation of Arenes, Heteroarenes, and Alkenes under Air
Singh, Bijaya Kumar
Bairy, Gurupada
Jana, Ranjan
CHEMISTRYSELECT, 2017, 2 (28): : 9227 - 9232
[32] Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex
Jud, Wolfgang
Maljuric, Snjezana
Kappe, C. Oliver
Cantillo, David
ORGANIC LETTERS, 2019, 21 (19) : 7970 - 7975
[33] Arenes and Heteroarenes C-H Functionalization Under Enabling Conditions: Electrochemistry, Photoelectrochemistry & Flow Technology
Murtaza, Ayesha
Ulhaq, Zia
Shirinfar, Bahareh
Rani, Sadia
Aslam, Samina
Martins, Guilherme M. M.
Ahmed, Nisar
CHEMICAL RECORD, 2023, 23 (10):
[34] Benzylamine promoted direct C-H arylation of arenes and heteroarenes via excitation with heat or light
Chatterjee, Souvik
Azmi, Sabnam
Bandopadhyay, Nilaj
Paramanik, Krishnendu
Sarkar, Gayetri
Biswas, Bhaskar
Das, Hari Sankar
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (46) : 9072 - 9077
[35] Iridium-Catalyzed Sequential Silylation and Borylation of Heteroarenes Based on Regioselective C-H Bond Activation
Murai, Masahito
Nishinaka, Naoki
Takai, Kazuhiko
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (20) : 5843 - 5847
[36] Visible-Light-Driven C-H Imidation of Arenes and Heteroarenes by a Phosphonium Ylide Organophotoredox Catalyst: Application to C-H Functionalization of Alkenes
Toda, Yasunori
Kobayashi, Toya
Hirai, Fumiya
Yano, Takamichi
Oikawa, Makoto
Sukegawa, Kimiya
Shimizu, Masahiro
Ito, Fuyuki
Suga, Hiroyuki
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (13): : 9574 - 9578
[37] Cobalt-Catalyzed C-H Borylation of Alkyl Arenes and Heteroarenes Including the First Selective Borylations of Secondary Benzylic C-H Bonds
Jayasundara, Chathurika R. K.
Sabasovs, Dmitrijs
Staples, Richard J.
Oppenheimer, Jossian
Smith, Milton R., III
Maleczka, Robert E., Jr.
ORGANOMETALLICS, 2018, 37 (10) : 1567 - 1574
[38] Improvements of efficiency and regioselectivity in the iridium(I)-catalyzed aromatic C-H silylation of arenes with fluorodisilanes
Saiki, Takeaki
Nishio, Yukihiro
Ishiyama, Tatsuo
Miyaura, Norio
ORGANOMETALLICS, 2006, 25 (26) : 6068 - 6073
[39] Nickel-Catalyzed C-H Silylation of Arenes with Vinylsilanes: Rapid and Reversible β-Si Elimination
Department of Chemistry and Biochemistry, University of Windsor, 401 Sunset Avenue, Windsor
ON
N9B 3P4, Canada
J. Am. Chem. Soc., 27 (9401-9407):
[40] Phosphorus(III)-assisted regioselective C–H silylation of heteroarenes
Dingyi Wang
Xiangyang Chen
Jonathan J. Wong
Liqun Jin
Mingjie Li
Yue Zhao
K. N. Houk
Zhuangzhi Shi
Nature Communications, 12

← 1 2 3 4 5 →