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

[21] ARYLATION OF AROMATIC HETEROCYCLES WITH ARENES AND PALLADIUM(II) ACETATE [J].

ITAHARA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5272-5275

[22] Catalytic functionalization of arenes and alkanes via C-H bond activation [J].

Jia, CG ;

Kitamura, T ;

Fujiwara, Y .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) :633-639

[23]

Kakiuchi F., 1999, ACTIVATION UNREACTIV, P47, DOI DOI 10.1038/417507A

[24] Oxidative C-H activation/C-C bond forming reactions: Synthetic scope and mechanistic insights [J].

Kalyani, D ;

Deprez, NR ;

Desai, LV ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7330-7331

[25]

Kalyani D, 2007, TOP ORGANOMETAL CHEM, V24, P85, DOI 10.1007/3418_2007_068

[26] Understanding and exploiting C-H bond activation [J].

Labinger, JA ;

Bercaw, JE .

NATURE, 2002, 417 (6888) :507-514

[27] Facile Pd-catalyzed cross-coupling of 2′-deoxyguanosine O6-arylsulfonates with arylboronic acids [J].

Lakshman, MK ;

Thomson, PF ;

Nuqui, MA ;

Hilmer, JH ;

Sevova, N ;

Boggess, B .

ORGANIC LETTERS, 2002, 4 (09) :1479-1482

[28] Palladium catalysis for the synthesis of hydrophobic C-6 and C-2 aryl 2′-deoxynucleosides.: Comparison of C-C versus C-N bond formation as well as C-6 versus C-2 reactivity [J].

Lakshman, MK ;

Hilmer, JH ;

Martin, JQ ;

Keeler, JC ;

Dinh, YQV ;

Ngassa, FN ;

Russon, LM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7779-7787

[29] Synthesis and photophysical properties of bis-cyclometallated Iridium(III)-Styryl complexes and their saturated analogues [J].

Lepeltier, Marc ;

Lee, Terence Kwok-Ming ;

Lo, Kenneth Kam-Wing ;

Toupet, Loic ;

Le Bozec, Hubert ;

Guerchais, Veronique .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2007, (18) :2734-2747

[30] Direct functionalization of nitrogen heterocycles via Rh-catalyzed C-H bond activation [J].

Lewis, Jared C. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (08) :1013-1025

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