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. Issue 10 (8th March 2019)

• Record Type: Journal Article
• Authors: Yamada, Mizuki; Matsumura, Mio; Sakaki, Erina; Yen, Shih-yun; Kawahata, Masatoshi; Hyodo, Tadashi; Yamaguchi, Kentaro; Murata, Yuki; Yasuike, Shuji
• Is Part Of: Tetrahedron. Volume 75:Issue 10(2019)
• Page Start: 1406
• Page End: 1414
• Publication Date: 2019-03-08
• Subjects: Three-component reaction -- Antimony -- Selenium -- Copper catalyst -- Selenide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.01.056
• Languages: English
• ISSNs: 0040-4020

Abstract

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. Graphical abstract: Image 1 Highlights: The Cu-catalyzed three-component reaction of organoantimony, azides, and selenium is described. The obtained selenides and diselenides having a 1, 2, 3-triazole ring are all novel compounds. This reaction provides regioselective double Se -arylation under simple reaction conditions.