Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.
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.
Department of Chemistry, Georgetown University , Washington, DC 20057, United States.
Peng
P
Zhang
Andrea M
AM
Cook
Yang
Y
Liu
Christian
C
Wolf
D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure
D000577:Amides; D006571:Heterocyclic Compounds; D006843:Hydrocarbons, Chlorinated; D003300:Copper