Zn(II)- or Ag(I)-catalyzed 1,4-metathesis reactions between 3-En-1-ynamides and nitrosoarenes
Sagar Ashok Gawade1, Deepak B Huple, Rai-Shung Liu
1Department of Chemistry, National Tsing-Hua University , Hsinchu, Taiwan, ROC.
Abstract:
Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 2-propynimidamides and benzaldehyde derivatives. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently. We have developed metathesis/alkynation cascades for unsubstituted 2-propynimidamides and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes. Both 1,4-oxoiminations and 1,4-hydroxyiminations increase the molecular complexity of products.
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