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Investigation of Hydrophosphorylation Reaction of Pentacoordinate Hydrospirophosphorane and Electron‐Deficient Alkenes Catalyzed by Organic Phosphine

Investigation of Hydrophosphorylation Reaction of Pentacoordinate Hydrospirophosphorane and... 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 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Investigation of Hydrophosphorylation Reaction of Pentacoordinate Hydrospirophosphorane and Electron‐Deficient Alkenes Catalyzed by Organic Phosphine

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References (40)

Publisher
Wiley
Copyright
© 2021 Wiley‐VCH GmbH
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.202100536
Publisher site
See Article on Publisher Site

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

Journal

Asian Journal of Organic ChemistryWiley

Published: Nov 1, 2021

Keywords: Organocatalysis; Pentacoordinate spirophosphorane; Hydrophosphorylation reaction; Electron-deficient alkene

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