Orthosilicate-Mediated Esterification of Monosubstituted Phosphinic Acids

  • 10.1021/ol006434g
  • Organic Letters
  • p 3341-3344, Volume 2, Issue 21,
  • journal-article
Monosubstituted phosphinic acids are esterified with orthosilicates in excellent yields. Phosphinylidene-containing acids react selectively under these conditions, while disubstituted phosphinic acids and phosphonic acids remain unchanged. One-pot procedures are also described for the preparation of phosphinate esters from an alcohol. This novel method provides a convenient and general alternative to more commonly employed conditions such as diazomethane or carbodiimide.

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Orthosilicate-Mediated Esterification of Monosubstituted Phosphinic Acids

The methodology developed by Montchamp and co-workers demonstrated a mild and reliable way to esterify the monosubstituted phosphinic acids.

 

I repeated the preparation of substrate 3 as the entry 5 in table 1 followed their protocol.  The reaction went smoothly to afford...

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