Copper-Catalyzed Three-Component Coupling Reaction of Azoles, Se Powder, and Aryl Iodides

被引：66

作者：

Gao, Chao ^{[1
]}

Wu, Ge ^{[2
]}

Min, Lin ^{[1
]}

Liu, Miaochang ^{[1
]}

Gao, Wenxia ^{[1
]}

Ding, Jinchang ^{[1
]}

Chen, Jiuxi ^{[1
]}

Huang, Xiaobo ^{[1
]}

Wu, Huayue ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[2] Wenzhou Med Univ, Sch Pharm, Wenzhou 325035, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 01期

基金：

中国国家自然科学基金;

关键词：

DIRECT ARYLATION; SELENIUM; BENZOXAZOLES; HALIDES; ORGANOSELENIUM; INHIBITOR; REAGENTS; AMINES;

D O I：

10.1021/acs.joc.6b02388

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed three-component coupling reaction of azoles, Se powder, and aryl iodide is described for the first time. This transformation provides a straightforward and facile pathway to synthesis 2-arylselanyl-azoles via a copper-catalyzed double C-Se bonds formation process. This reaction is attractive and practical since the cheap copper catalyst is employed and it does not require ligands, proceeds in generally good yields, and has a broad range of functional groups tolerance.

引用

页码：250 / 255

页数：6

共 29 条

[1] Synthesis and free radical polymerization of p-methylseleno- and p-phenylselenostyrenes [J].

Ando, T ;

Kwon, TS ;

Kitagawa, A ;

Tanemura, T ;

Kondo, S ;

Kunisada, H ;

Yuki, Y .

MACROMOLECULAR CHEMISTRY AND PHYSICS, 1996, 197 (09) :2803-2810

[2] THE METATHESIS OF N-SILYLAMINES AND BENZENESELENENYL CHLORIDE - AN EFFICIENT SELENENAMIDE SYNTHESIS [J].

BACK, TG ;

KERR, RG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (02) :308-310

[3] Cu-Catalyzed Efficient Synthetic Methodology for Ebselen and Related Se-N Heterocycles [J].

Balkrishna, Shah Jaimin ;

Bhakuni, Bhagat Singh ;

Chopra, Deepak ;

Kumar, Sangit .

ORGANIC LETTERS, 2010, 12 (23) :5394-5397

[4] Solvent-Controlled Halo-Selective Selenylation of Aryl Halides Catalyzed by Cu(II) Supported on Al2O3. A General Protocol for the Synthesis of Unsymmetrical Organo Mono- and Bis-Selenides [J].

Chatterjee, Tanmay ;

Ranu, Brindaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) :7145-7153

[5] Copper-Catalyzed Trifluoromethylselenolation of Aryl and Alkyl Halides: The Silver Effect in Transmetalation [J].

Chen, Chaohung ;

Hou, Chuanqi ;

Wang, Yuguang ;

Hor, T. S. Andy ;

Weng, Zhiqiang .

ORGANIC LETTERS, 2014, 16 (02) :524-527

[6] Copper-catalyzed arylation of heterocycle C-H bonds [J].

Do, Hien-Quang ;

Daugulis, Olafs .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) :12404-+

[7] SYNTHESIS, ANTIOXIDANT PROPERTIES, BIOLOGICAL-ACTIVITY AND MOLECULAR MODELING OF A SERIES OF CHALCOGEN ANALOGS OF THE 5-LIPOXYGENASE INHIBITOR DUP-654 [J].

ENGMAN, L ;

STERN, D ;

FRISELL, H ;

VESSMAN, K ;

BERGLUND, M ;

EK, B ;

ANDERSSON, CM .

BIOORGANIC & MEDICINAL CHEMISTRY, 1995, 3 (09) :1255-1262

[8] Base-promoted cascade reaction of isocyanides, selenium and amines: a practical approach to 2-aminobenzo[d][1,3] selenazines under metal-free conditions [J].

Fang, Yi ;

Wang, Shun-Yi ;

Shen, Xiao-Bin ;

Ji, Shun-Jun .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (10) :1338-1341

[9] Synthesis of diaryl selenides using electrophilic selenium species and nucleophilic boron reagents in ionic liquids [J].

Freitas, Camilo S. ;

Barcellos, Angelita M. ;

Ricordi, Vanessa G. ;

Pena, Jesus M. ;

Perin, Gelson ;

Jacob, Raquel G. ;

Lenardao, Eder J. ;

Alves, Diego .

GREEN CHEMISTRY, 2011, 13 (10) :2931-2938

[10] Novel synthesis of silver selenide nano-powder from silver nitrate and organo-selenium compound [J].

Khanna, PK ;

Das, BK .

MATERIALS LETTERS, 2004, 58 (06) :1030-1034

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