4.4 Article

T3P®-assisted esterification and amidation of phosphinic acids

Journal

TETRAHEDRON
Volume 70, Issue 44, Pages 8280-8285

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.09.021

Keywords

Phosphinic acid; Phosphinic amide; P-Heterocycles; Phosphinate; T3P (R) reagent; Green synthesis

Funding

  1. Hungarian Scientific Research Fund [OTKA K83118]

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A few phosphinic acids, such as phenylphosphinic acids, 1-hydroxy-3-phospholene 1-oxides and 1-hydroxyphospholane oxides are esterified with simple alcohols in the presence of propylphosphonic anhydride (T3P (R)). If 1.1 equiv of the T3P (R) reagent is used, the esterifications are fast and efficient at 25 degrees C. In the case of more reactive models it was enough to apply 0.66 equiv of T3P (R) at 85 degrees C under microwave conditions. The amidation of 1-hydroxy-3-methyl-3-phospholene oxide could also be accomplished under similar conditions. (C) 2014 Elsevier Ltd. All rights reserved.

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