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Irregularities in the Effect of Potassium Phosphate in Ynamide Synthesis

Karin Dooleweerdt, Henrik Birkedal, Thomas Ruhland and Troels Skrydstrup*

*Department of Chemistry and the Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark, Email:

K. Dooleweerd, H. Birkedal, T. Ruhland, T. Skrydstrup, J. Org. Chem., 2008, 73, 9447-9450.

DOI: 10.1021/jo801935b


In copper-catalyzed direct N-alkynylation, the use of pure and anhydrous K3PO4 provides higher ynamide yields in comparison to samples contaminated with hydrates (K3PO4 1.5 H2O and K3PO4 7 H2O). With high quality K3PO4, a number of ynamides were synthesized in good yields. In addition, ynamides can undergo regioselective hydroamination with carbamates.

see article for more examples


This publication refers to a method by Richard P. Hsung. See for example:

Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and Z-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides

X. Zhang, Y. Zhang, J. Huang, R. P. Hsung, K. C. M. Kurtz, J. Oppenheimer, M. E. Petersen, I. K. Sagamanova, L. Shen, M. R. Tracey, J. Org. Chem., 2006, 71, 4170-4177.

Reto Mueller, March 25, 2010

Key Words

Ynamides, Sulfonamides

ID: J42-Y2008-3620