Copper-catalyzed direct and odorless selenylation with a sodium selenite-based reagent

被引：29

作者：

Cao, Yuan ^{[1
]}

Liu, Jie ^{[1
]}

Liu, Fanmin ^{[1
]}

Jiang, Lvqi ^{[1
]}

Yi, Wenbin ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, Nanjing 210094, Jiangsu, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 06期

基金：

中国国家自然科学基金;

关键词：

SELENOORGANIC COMPOUND EBSELEN; ANTIOXIDANT PROPERTIES; DIRECT SELENATION; C(SP(2))-H BONDS; ORGANOSELENIUM; THIOREDOXIN; INHIBITION; INDOLES; ACID; ARYL;

D O I：

10.1039/c8qo01355a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method using a sodium selenite-based (NaO2SeR) direct selenylation reagent has been developed. NaO2SeR is odorless, shelf-stable, easy to handle, practical and scalable. Good yields and a broad functional group compatibility were observed when it was reacted with indoles, a furan, pyrrole and ketones under reductive conditions to afford the corresponding organoselenium products.

引用

页码：825 / 829

页数：5

共 63 条

[1] REACTION OF BENZENESELENENYL HALIDES WITH ESTROGENS [J].

ALI, H ;

VANLIER, JE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :269-271

[2] The selenium to selenoprotein pathway in eukaryotes: More molecular partners than anticipated [J].

Allmang, Christine ;

Wurth, Laurence ;

Krol, Alain .

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2009, 1790 (11) :1415-1423

[3] Scavenging of hypochlorous acid by carvedilol and ebselen in vitro [J].

Aruoma, OI .

GENERAL PHARMACOLOGY, 1997, 28 (02) :269-272

[4] COMPARATIVE OXIDATION OF PHENOLS WITH BENZENESELENINIC ANHYDRIDE AND WITH BENZENESELENINIC ACID [J].

BARTON, DHR ;

FINET, JP ;

THOMAS, M .

TETRAHEDRON, 1988, 44 (20) :6397-6406

[5] INTERACTION OF THE ANTIINFLAMMATORY SELENOORGANIC COMPOUND EBSELEN WITH ACID-SECRETION IN ISOLATED PARIETAL-CELLS AND GASTRIC H+/K+-ATPASE [J].

BEIL, W ;

STAAR, U ;

SEWING, KF .

BIOCHEMICAL PHARMACOLOGY, 1990, 40 (09) :1997-2003

[6]

BJORNSTEDT M, 1992, J BIOL CHEM, V267, P8030

[7]

Bjornstedt M, 1997, BIOMED ENVIRON SCI, V10, P271

[8] Lewis base activation of lewis acids: Development of a Lewis base catalyzed selenolactonization [J].

Denmark, Scott E. ;

Collins, William R. .

ORGANIC LETTERS, 2007, 9 (19) :3801-3804

[9] Synthesis and Selective Anticancer Activity of Organochalcogen Based Redox Catalysts [J].

Doering, Mandy ;

Ba, Lalla A. ;

Lilienthal, Nils ;

Nicco, Carole ;

Scherer, Christiane ;

Abbas, Muhammad ;

Zada, Abdul Ali Peer ;

Coriat, Romain ;

Burkholz, Torsten ;

Wessjohann, Ludger ;

Diederich, Marc ;

Batteux, Frederic ;

Herling, Marco ;

Jacob, Claus .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) :6954-6963

[10] Organosulfur compounds: Electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions [J].

Dubbaka, SR ;

Vogel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7674-7684

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