Aerobic copper-catalyzed homo-coupling of azaallyl anions: A facile access to vicinal diamines. (22nd June 2022)

• Record Type: Journal Article
• Authors: Shen, Mei-Hua; Guo, Bin; Li, Chen; Sun, Chen-Lei; Zhu, Yi-Fan; Zhu, Chifan; Xu, Hua-Dong; Xu, Defeng
• Is Part Of: Tetrahedron letters. Volume 100(2022)
• Publication Date: 2022-06-22
• Subjects: Copper catalysis -- Homo-coupling of azaallyl anions -- Aerobic oxidation -- Oxidative coupling -- 1, 2-Diamine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153886
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Agitating a mixture of N-(diphenylmethyl)arylaldimine, t BuOK and catalytic CuCl2 in THF under O2 atmosphere at 75 °C for several hours produces corresponding vicinal diimine. This transformation takes place via a copper-catalyzed oxidative homo-coupling of the in situ generated azaallyl anion, in which molecular oxygen serves as the effective terminal oxidant. 1, 2-diarylethane-1, 2-diamine dihydrochloride is obtained upon hydrolysis with hydrochloric acid.