Phosphinoyl radical-initiated vicinal hydroxy-phosphorylation of alkenes. Issue 47 (22nd November 2019)

• Record Type: Journal Article
• Authors: Shoberu, Adedamola; Li, Shuai-Shuai; Zhang, Guo-Yu; Li, Da-Peng; Zou, Jian-Ping
• Is Part Of: Tetrahedron. Volume 75:Issue 47(2019)
• Publication Date: 2019-11-22
• Subjects: Manganese(III) acetate -- Styrenes -- Difunctionalization reaction -- Phosphorus-centered radical reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.130683
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A protocol of Mn(OAc)3 –mediated α, β -hydroxy-phosphorylation of alkenes with phosphorus-centered radicals generated from diphenylphosphine oxide is described. A combination of steric and electronic factors played an important role in this reaction. The reactions of styrenes bearing ortho -substituent gave the selective β -hydroxyphosphine oxide products. Graphical abstract: Image 1 Highlights: The reactions of styrenes bearing ortho -substituent gave the selective β -hydroxyphosphine oxide products via a radical passway. A combination of steric and electronic factors played an important role in this reaction.