Login / Signup

Uniting Amide Synthesis and Activation by PIII/PV-Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines.

Jeffrey M LipshultzAlexander T Radosevich
Published in: Journal of the American Chemical Society (2021)
An organophosphorus (PIII/PV redox) catalyzed method for the three-component condensation of amines, carboxylic acids, and pyridine N-oxides to generate 2-amidopyridines via serial dehydration is reported. Whereas amide synthesis and functionalization usually occur under divergent reaction conditions, here a phosphetane catalyst (together with a mild bromenium oxidant and terminal hydrosilane reductant) is shown to drive both steps chemoselectively in an auto-tandem catalytic cascade. The ability to both prepare and functionalize amides under the action of a single organocatalytic reactive intermediate enables new possibilities for the efficient and modular preparation of medicinal targets.
Keyphrases
  • room temperature
  • ionic liquid
  • electron transfer
  • highly efficient
  • molecularly imprinted
  • reduced graphene oxide
  • mass spectrometry
  • gold nanoparticles