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Kinetics and mechanism of Horner–Wadsworth–Emmons reaction of weakly acidic phosphonate in solid–liquid phase-transfer catalysis system

Authors
Journal
Catalysis Communications
1566-7367
Publisher
Elsevier
Publication Date
Volume
36
Identifiers
DOI: 10.1016/j.catcom.2013.03.015
Keywords
  • Horner–Wadsworth–Emmons Reactions
  • Solid–Liquid Phase-Transfer Catalysis
  • Interfacial Mechanism
  • The Weakly Acidic Substrate
Disciplines
  • Chemistry
  • Mathematics

Abstract

Abstract Homer–Wadsworth–Emmons (HWE) reaction of diethyl benzylphosphonate (DEBP, pKa=27.55) with aldehyde was performed in a solid–liquid phase-transfer catalysis (SL–PTC) system using sodium hydroxide as the solid phase. Various parameters that influenced the pseudo-first-order rate constant including stirring speed, catalysts, salt, water and temperature were investigated to explore the process of the generation and transfer of the active intermediate. A reasonable interfacial mechanism of the PTC reaction of the weakly acidic substrate was proved for the first time. HWE reactions under SL–PTC conditions showed high activity and geometric selectivity. It is anticipated that this simple and controllable synthesis method should provide a new idea for HWE reaction in chemical industry.

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