CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids

被引：94

作者：

Alves, Diego ^{[1
]}

Santos, Cayane G. ^{[1
]}

Paixao, Marcio W. ^{[4
]}

Soares, Letiere C. ^{[2
]}

de Souza, Diego ^{[2
]}

Rodrigues, Oscar E. D. ^{[2
]}

Braga, Antonio L. ^{[3
]}

机构：

[1] UNIFRA, Ctr Univ Franciscano, BR-97010032 Santa Maria, RS, Brazil

[2] Univ Fed Santa Maria, Dept Quim, BR-97105900 Santa Maria, RS, Brazil

[3] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC, Brazil

[4] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 48期

关键词：

UNSYMMETRICAL DIARYL SELENIDES; NUCLEOPHILIC SUBSTITUTIONS; ORGANOSELENIUM COMPOUNDS; ORGANOBORONIC ACIDS; SE-SE; C-N; HALIDES; IODIDE; TELLURIDES; CHEMISTRY;

D O I：

10.1016/j.tetlet.2009.09.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present here an efficient and ligand-free cross-coupling reaction of organic diselenides with aryl boronic acids using a catalytic amount of CuO nanoparticles in DMSO at 100 degrees C under air atmosphere. This is a general cross-coupling reaction and was performed with organic diselenides and aryl boronic acids bearing electron-withdrawing and electron-donating groups affording the corresponding selenides in good to excellent yields. The CuO nanoparticles can be easily recovered and utilized for further catalytic reactions. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6635 / 6638

页数：4

共 48 条

[1] RELATIVE REACTIVITIES OF AMIDE, DIPHENYLPHOSPHIDE, AND DIPHENYLARSENIDE IONS TOWARD ARYL RADICALS [J].

ALONSO, RA ;

BARDON, A ;

ROSSI, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (19) :3584-3587

[2] Copper Catalyzed Cross-Coupling Reactions of Diaryl Ditellurides with Potassium Aryltrifluoroborate Salts [J].

Alves, Diego ;

Pena, Jesus M. ;

Vieira, Adriano S. ;

Botteselle, Giancarlo V. ;

Guadagnin, Rafael C. ;

Stefani, Helio A. .

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2009, 20 (05) :988-U262

[3]

Andersson C.-M., 1996, Advances in the development of pharmaceutical antioxidants," in, P65

[4] ANTIOXIDANT ACTIVITY OF SOME DIARYLSELENIDES IN BIOLOGICAL-SYSTEMS [J].

ANDERSSON, CM ;

HALLBERG, A ;

LINDEN, M ;

BRATTSAND, R ;

MOLDEUS, P ;

COTGREAVE, I .

FREE RADICAL BIOLOGY AND MEDICINE, 1994, 16 (01) :17-28

[5] Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].

Astruc, D ;

Lu, F ;

Aranzaes, JR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872

[6]

Astruc D., 2008, NANOPARTICLES CATALY

[7] Palladium nanoparticles as efficient green homogeneous and heterogeneous carbon-carbon coupling precatalysts: A unifying view [J].

Astruc, Didier .

INORGANIC CHEMISTRY, 2007, 46 (06) :1884-1894

[8] OXIDATION OF ORGANOSELENIUM COMPOUNDS BY OZONE [J].

AYREY, G ;

BARNARD, D ;

WOODBRIDGE, DT .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (JUN) :2089-&

[9] The impact of nanoscience on heterogeneous catalysis [J].

Bell, AT .

SCIENCE, 2003, 299 (5613) :1688-1691

[10] Synthesis of new chiral aliphatic amino diselenides and their application as catalysts for the enantioselective addition of diethylzinc to aldehydes [J].

Braga, AL ;

Paixao, MW ;

LUdtke, DS ;

Silveira, CC ;

Rodrigues, OED .

ORGANIC LETTERS, 2003, 5 (15) :2635-2638

← 1 2 3 4 5 →