Copper-catalyzed direct hydroxyphosphorylation of electron-deficient alkenes with H-phosphine oxides and dioxygen. Issue 21 (24th May 2017)

• Record Type: Journal Article
• Authors: Yi, Dong; Fu, Qiang; Chen, Su-Yuan; Gao, Ming; Yang, Lu; Zhang, Zhi-Jie; Liang, Wu; Zhang, Qiang; Ji, Jian-Xin; Wei, Wei
• Is Part Of: Tetrahedron letters. Volume 58:Issue 21(2017)
• Page Start: 2058
• Page End: 2061
• Publication Date: 2017-05-24
• Subjects: Electron-deficient alkenes -- Hydroxyphosphorylation -- β-Hydroxyphosphine oxide -- Copper catalysis -- Dioxygen; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.04.042
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: An efficient copper-catalyzed direct hydroxyphosphorylation of electron-deficient alkenes with H-phosphine oxides and dioxygen leading to β-hydroxyphosphine oxides has been realized at room temperature. Highlights: Direct hydroxyphosphorylation of electron-deficient alkenes. The hydroxyl oxygen atom of β-hydroxyphosphine oxide originated from dioxygen. The reaction can be performed in scaled-up manner under very mild conditions. A radical process might be involved in this hydroxyphosphorylation. Abstract: A copper-catalyzed direct hydroxyphosphorylation of electron-deficient alkenes with H-phosphine oxides and dioxygen is reported. The present reaction, proceeds under mild reaction conditions with good functional group tolerance, affording the facile and efficient synthesis of various β-hydroxyphosphine oxides in a scaled-up manner with moderate to good yields.