Copper catalyzed one-pot synthesis of β-ketophosphine oxides from ketones and H-phosphine oxides. Issue 25 (21st June 2017)

• Record Type: Journal Article
• Authors: Zhang, Zhi-Jie; Yi, Dong; Fu, Qiang; Liang, Wu; Chen, Su-Yuan; Yang, Lu; Du, Feng-Tian; Ji, Jian-Xin; Wei, Wei
• Is Part Of: Tetrahedron letters. Volume 58:Issue 25(2017)
• Page Start: 2417
• Page End: 2420
• Publication Date: 2017-06-21
• Subjects: Copper-catalysis -- One-pot procedure -- β-Ketophosphine oxides -- Ketones -- Vinylhydrazinedicarboxylates; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.05.005
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: A simple and efficient copper-catalyzed method has been developed for the synthesis of β-ketophosphine oxides from ketones and H-phosphine oxides in one-pot procedure at room temperature. Highlights: One-pot synthesis of β-ketophosphine oxides from ketones and H-phosphine oxides. The present oxyphosphorylation reaction can be performed under air at room temperature. The carbonyl oxygen atom of β-ketophosphine oxides originated from dioxygen. A radical process is proposed. Abstract: A facile and efficient copper catalyzed one-pot method has been developed for the formation of β-ketophosphine oxides from ketones and H-phosphine oxides under air at room temperature, in which vinylhydrazinedicarboxylate was formed as the key intermediate. Preliminary mechanistic studies indicated that the reaction might involve a radical process and carbonyl oxygen atom of β-ketophosphine oxides came from molecular oxygen.