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: tschem.au.dk

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

DOI: 10.1021/jo801935b

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Abstract

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

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Note

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

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Key Words

Ynamides, Sulfonamides

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ID: J42-Y2008-3620