Unexpected C-Se Cross-Coupling Reaction: Copper Oxide Catalyzed Synthesis of Symmetrical Diaryl Selenides via Cascade Reaction of Selenourea with Aryl Halides/Boronic Acids

被引:48
作者
Reddy, V. Prakash [1 ]
Kumar, A. Vijay [1 ]
Rao, K. Rama [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem 1, Hyderabad 500007, Andhra Pradesh, India
关键词
STEREOSELECTIVE-SYNTHESIS; GLUTATHIONE-PEROXIDASE; UNSYMMETRICAL DIARYL; ORGANOSELENIUM COMPOUNDS; DIORGANO DISELENIDES; VINYL SELENIDES; HALIDES; IODIDE; CHEMISTRY; ARYLATION;
D O I
10.1021/jo102017g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Selenourea is used as an effective selenium surrogate in the C Se cross-coupling reaction catalyzed by copper oxide nanoparticles under ligand free conditions. This protocol has been utilized for the synthesis of a variety of symmetrical diaryl selenides in good to excellent yields from the readily available aryl halides/boronic acids.
引用
收藏
页码:8720 / 8723
页数:4
相关论文
共 56 条
[1]   CuO nanoparticles: an efficient and recyclable catalyst for cross-coupling reactions of organic diselenides with aryl boronic acids [J].
Alves, Diego ;
Santos, Cayane G. ;
Paixao, Marcio W. ;
Soares, Letiere C. ;
de Souza, Diego ;
Rodrigues, Oscar E. D. ;
Braga, Antonio L. .
TETRAHEDRON LETTERS, 2009, 50 (48) :6635-6638
[2]  
Andersson C.-M., 1996, Advances in the development of pharmaceutical antioxidants," in, P65
[3]   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
[4]  
[Anonymous], 1999, ORGANOSELENIUM CHEM
[5]   Diselenides and allyl selenides as glutathione peroxidase mimetics.: Remarkable activity of cyclic seleninates produced in situ by the oxidation of allyl ω-hydroxyalkyl selenides [J].
Back, TG ;
Moussa, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13455-13460
[6]  
Beletskaya I. P., 2000, J ORGANOMET CHEM, V96, P605
[7]   Copper(I)-catalyzed arylselenylation of aryl bromides and iodides [J].
Beletskaya, IP ;
Sigeev, AS ;
Peregudov, AS ;
Petrovskii, PV .
TETRAHEDRON LETTERS, 2003, 44 (37) :7039-7041
[8]   Al2O3-Supported Cu-Catalyzed Electrophilic Substitution by PhSeBr in Organoboranes, Organosilanes, and Organostannanes. A Protocol for the Synthesis of Unsymmetrical Diaryl and Alkyl Aryl Selenides [J].
Bhadra, Sukalyan ;
Saha, Amit ;
Ranu, Brindaban C. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14) :4864-4867
[9]   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
[10]   Modular chiral selenium-containing oxazolines:: synthesis and application in the palladium-catalyzed asymmetric allylic alkylation [J].
Braga, AL ;
Lüdtke, DS ;
Sehnem, JA ;
Alberto, EE .
TETRAHEDRON, 2005, 61 (49) :11664-11671