Direct catalytic C-H arylation of imidazo[1,2-a]pyridine with aryl bromides using magnetically recyclable Pd-Fe3O4 nanoparticles

被引：55

作者：

Lee, Jaewoo ^{[1
]}

Chung, Jooyoung ^{[1
]}

Byun, Sang Moon ^{[1
]}

Kim, B. Moon ^{[1
]}

Lee, Chulbom ^{[1
]}

机构：

[1] Seoul Natl Univ, Dept Chem, Seoul 151747, South Korea

来源：

TETRAHEDRON | 2013年 / 69卷 / 27-28期

基金：

新加坡国家研究基金会;

关键词：

Direct arylation; Recyclable magnetic nanoparticles; Pd-Fe3O4; Imidazo[1,2-a]pyridine; Aryl bromides; LIGAND-FREE PALLADIUM; COUPLING REACTIONS; HETEROAROMATIC-COMPOUNDS; FE3O4; NANOPARTICLES; HYDRAZINE HYDRATE; BOND ACTIVATION; COMPLEXES; FUNCTIONALIZATION; NANOCATALYSTS; IMIDAZOLES;

D O I：

10.1016/j.tet.2013.04.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct C-H arylation of a heteroarene with aryl bromides has been achieved under the catalysis of magnetic nanoparticles. In the presence of bimetallic Pd-Fe3O4 heterodimer nanocrystals (1 mol % in palladium), the reaction of imidazo[1,2-a]pyridine with various aryl bromides gives the corresponding arylated products with exclusive C3-selectivity. The highly regioselective method is applicable to a wide range of aryl bromides with varying electronic and steric properties. The Pd-Fe3O4 nanocrystals can be recoverable by simple magnetic separation and have been recycled ten times without loss of catalytic activity. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5660 / 5664

页数：5

共 49 条

[1] 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

[2] Ruthenium-Catalyzed Direct Arylations of N-Aryl 1,2,3-Triazoles with Aryl Chlorides as Electrophiles [J].

Ackermann, Lutz ;

Born, Robert ;

Vicente, Ruben .

CHEMSUSCHEM, 2009, 2 (06) :546-549

[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] Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C-H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2009, 65 (50) :10269-10310

[5] Direct C-3-Arylations of 1H-Indazoles [J].

Ben-Yahia, Ali ;

Naas, Mohammed ;

El Kazzouli, Said ;

Essassi, El Mokhtar ;

Guillaumet, Gerald .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (36) :7075-7081

[6] Direct Arylation of Imidazo[1,2-a]pyridine at C-3 with Aryl Iodides, Bromides, and Triflates via Copper(I)-Catalyzed C-H Bond Functionalization [J].

Cao, Hua ;

Zhan, Haiying ;

Lin, Yuanguang ;

Lin, Xiulian ;

Du, Zuodong ;

Jiang, Huanfeng .

ORGANIC LETTERS, 2012, 14 (07) :1688-1691

[7]

Cavinet J., 2009, ORG LETT, V11, P1733

[8] Catalytic C-C coupling through C-H arylation of arenes or heteroarenes [J].

Chiusoli, Gian Paolo ;

Catellani, Marta ;

Costa, Mirco ;

Motti, Elena ;

Della Ca', Nicola ;

Maestri, Giovanni .

COORDINATION CHEMISTRY REVIEWS, 2010, 254 (5-6) :456-469

[9] Homeopathic ligand-free palladium as a catalyst in the Heck reaction. A comparison with a palladacycle [J].

de Vries, AHM ;

Mulders, JMCA ;

Mommers, JHM ;

Henderickx, HJW ;

de Vries, JG .

ORGANIC LETTERS, 2003, 5 (18) :3285-3288

[10] A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds [J].

Do, Hien-Ouang ;

Khan, Rana M. Kashif ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :15185-15192

← 1 2 3 4 5 →