Investigation of Hydrophosphorylation Reaction of Pentacoordinate Hydrospirophosphorane and Electron‐Deficient Alkenes Catalyzed by Organic Phosphine. Issue 11 (7th October 2021)

• Record Type: Journal Article
• Authors: Guo, Shanqi; Han, Kehui; Wang, Di; Guo, Yanchun; Cao, Shuxia; Zhao, Yufen
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 11(2021)
• Page Start: 3028
• Page End: 3033
• Publication Date: 2021-10-07
• Subjects: Organocatalysis -- Pentacoordinate spirophosphorane -- Hydrophosphorylation reaction -- Electron-deficient alkene; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100536
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: PR3 efficiently catalyzes the addition of H‐spirophosphorane to electron‐deficient alkenes to give the spirophosphoranes with a pentacoordinate P−C bond in moderate to excellent yields. This practical procedure was conducted by using PR3 as an organocatalyst, which avoided the use of an additional base, traditional heating, and metal reagents. The investigation of the reaction mechanism showed that the zwitterion intermediate served as the base to further catalyze hydrospirophosphorane. Then the spirophosphoranide formed as a nucleophile attacked electron‐deficient alkene to give the addition products. This reaction is a first and simple hydrophosphorylation reaction of alkenes to construct pentacoordinate P−C bond under organocatalysis Abstract : A general and metal‐free hydrophosphorylation reaction procedure at room temperature was described for the synthesis of spirophosphoranes with pentacoordinate P−C bond. This practical procedure was conducted by using PR3 as an organocatalyst under mild conditions, which avoided the use of an additional base, traditional heating, and metal reagents.