Direct C-H Arylations of Unactivated Arenes Catalyzed by Amido-Functionalized Imidazolium Salts

被引：38

作者：

Ghosh, Debalina ^{[1
]}

Lee, Jhen-Yi ^{[1
]}

Liu, Chian-Yu ^{[1
]}

Chiang, Yen-Hsin ^{[1
]}

Lee, Hon Man ^{[1
]}

机构：

[1] Natl Changhua Univ Educ, Dept Chem, Changhua 50058, Taiwan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 2-3期

关键词：

CH activation; imidazolium salts; organocatalysis; transition metal-free conditions; unactivated arenes; CROSS-COUPLING REACTIONS; ARYL BOND FORMATION; HALIDES; HETEROCYCLES; ACTIVATION; NITROGEN; COMPLEXES; MOLECULES; CHLORIDES; BUTOXIDE;

D O I：

10.1002/adsc.201300877

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of biaryls from unactivated arenes and a broad range of aryl bromides and chlorides via the direct CH functionalization can be efficiently performed with the aid of amido-functionalized imidazolium salts as organocatalysts. This method avoids the use of toxic transition metal catalysts and organometallic reagents.

引用

页码：406 / 410

页数：5

共 37 条

[1]

Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996

[2] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[4] Direct Transition-Metal-Free Intramolecular Arylation of Phenols [J].

Bajracharya, Gan B. ;

Daugulis, Olafs .

ORGANIC LETTERS, 2008, 10 (20) :4625-4628

[5] Atroposelective synthesis of axially chiral biaryl compounds [J].

Bringmann, G ;

Mortimer, AJP ;

Keller, PA ;

Gresser, MJ ;

Garner, J ;

Breuning, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427

[6]

Bringmann G., 2005, ANGEW CHEM INT EDIT, V117, P5518, DOI 10.1002/ange.200462661

[7] Room-Temperature Photoinduced Direct C-H-Arylation via Base-Promoted Homolytic Aromatic Substitution [J].

Buden, Maria E. ;

Guastavino, Javier F. ;

Rossi, Roberto A. .

ORGANIC LETTERS, 2013, 15 (06) :1174-1177

[8] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].

Campeau, LC ;

Fagnou, K .

CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264

[9] Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes [J].

Chen, Wen-Ching ;

Hsu, Yu-Chen ;

Shih, Wei-Chun ;

Lee, Ching-Yu ;

Chuang, Wen-Han ;

Tsai, Yi-Fang ;

Chen, Peter Ping-Yu ;

Ong, Tiow-Gan .

CHEMICAL COMMUNICATIONS, 2012, 48 (53) :6702-6704

[10] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Do, Hien-Quang ;

Shabashov, Dmitry .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086

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