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Mechanistic Insight into the Catalytic Staudinger Ligation.

Paul B WhiteSjoerd J RijpkemaRoderick P BunschotenJasmin Mecinovic
Published in: Organic letters (2019)
Organophosphorus-catalyzed Staudinger ligation between carboxylic acids and azides in the presence of phenylsilane reductant produces amides. NMR-based mechanistic investigations revealed that the catalytic Staudinger ligation does not proceed via reduction of phosphine oxide but rather via reduction of iminophosphorane, which can subsequently undergo several transformations to produce the amide product.
Keyphrases
  • magnetic resonance
  • high resolution
  • single cell
  • crystal structure
  • room temperature