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Copper-catalyzed three-component reaction of ethynylstibanes, organic azides, and selenium: A simple and efficient synthesis of novel selenides and diselenides having 1,2,3-triazole rings

Authors :
Masatoshi Kawahata
Yuki Murata
Erina Sakaki
Mizuki Yamada
Shuji Yasuike
Mio Matsumura
Kentaro Yamaguchi
Shih-yun Yen
Tadashi Hyodo
Source :
Tetrahedron. 75:1406-1414
Publication Year :
2019
Publisher :
Elsevier BV, 2019.

Abstract

A simple method for the synthesis of monoselenides and diselenides having 1,2,3-triazole ring is described herein. The three component reaction of ethynylstibanes, organic azides, and selenium powder is catalyzed by CuI (10 mol%) using 1,10-phenanthroline as the ligand (10 mol%) under aerobic conditions. Either selenides or diselenides can be synthesized by selecting the appropriate amount of selenium powder for otherwise identical reaction conditions. The obtained selenides and diselenides having a 1,2,3-triazole ring are all novel compounds. By using an antimony reagent, this one-pot reaction provides regioselective double Se-arylation under simple reaction conditions.

Details

ISSN :
00404020
Volume :
75
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........a8b721e470ddb0e2400e709a2f614a56
Full Text :
https://doi.org/10.1016/j.tet.2019.01.056