Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles

J Org Chem. 2014 May 2;79(9):4167-73. doi: 10.1021/jo500365h. Epub 2014 Apr 18.

Abstract

The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon-carbon bond formation provides convenient access to a variety of 3-aminoynones from aliphatic and aromatic acyl chlorides in up to 99% yield. The addition to pyridines and quinolines occurs under almost identical conditions and proceeds with good to high regioselectivity, producing the corresponding 1,2-dihydro-N-heterocycles in up to 95% yield.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry*
  • Hydrocarbons, Chlorinated / chemistry*
  • Molecular Structure

Substances

  • Amides
  • Heterocyclic Compounds
  • Hydrocarbons, Chlorinated
  • Copper