Direct Arylation of 6-Phenylpurine and 6-Arylpurine Nucleosides by Ruthenium-Catalyzed C-H Bond Activation

被引：94

作者：

Lakshman, Mahesh K. ^{[1
]}

Deb, Ashoke C. ^{[1
]}

Chamala, Raghu Ram ^{[1
]}

Pradhan, Padmanava ^{[1
]}

Pratap, Ramendra ^{[1
]}

机构：

[1] CUNY City Coll, Dept Chem, New York, NY 10031 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 48期

关键词：

arylation; C-H activation; homogeneous catalysis; nucleosides; ruthenium; CARBON-HYDROGEN BONDS; MECHANISTIC INSIGHTS; COUPLING REACTIONS; ORGANIC-SYNTHESIS; ARYL IODIDES; FUNCTIONALIZATION; PALLADIUM; ARENES; COMPLEXES; CHLORIDES;

D O I：

10.1002/anie.201104035

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

One aryl or two? The title reaction predominantly gives the monoarylation products with various amounts of diarylation product being observed in almost all cases (see scheme). Aryl iodides as well as aryl bromides were reactive under the optimized reaction conditions. The multiple nitrogen atoms in the purine, and oxygen atoms in the saccharide posed no problems in these transformations. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11400 / 11404

页数：5

共 45 条

[1] Phosphine oxides as preligands in ruthenium-catalyzed arylations via C-H bond functionalization using aryl chlorides [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (14) :3123-3125

[2]

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

[3] [RuCl3(H2O)n]-catalyzed direct arylations [J].

Ackermann, Lutz ;

Althammer, Andreas ;

Born, Robert .

TETRAHEDRON, 2008, 64 (26) :6115-6124

[4] 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

[5] 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

[6]

Campeau LC, 2007, ALDRICHIM ACTA, V40, P35

[7] Direct C-H arylation of purines:: Development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines [J].

Cerna, Igor ;

Pohl, Radek ;

Klepetarova, Blanka ;

Hocek, Michal .

ORGANIC LETTERS, 2006, 8 (23) :5389-5392

[8]

Chen X., 2009, ANGEW CHEM, V121, P5196

[9] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].

Chen, Xiao ;

Engle, Keary M. ;

Wang, Dong-Hui ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115

[10] Peroxide-promoted regioselective arylation of 2-phenylpyridines and related substrates with aryl iodides [J].

Cheng, Kai ;

Zhang, Yuhong ;

Zhao, Jinlong ;

Xie, Chunsong .

SYNLETT, 2008, (09) :1325-1330

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