N-picolinamides as ligands for Ullmann-type homocoupling reactions

Fehmi Damkaci, Esra Altay, Matthew Waldron, Michael A. Knopp, David Snow, Nicholas Massaro

Research output: Contribution to journalArticlepeer-review

9 Scopus citations


The use of N-phenylpicolinamide (NPPA) as a ligand in Ullmann-type homocoupling reactions of aryl iodides and bromides in common solvents, such as DMF and MeCN has been successfully demonstrated at room temperature. In addition, this work provided the first example of the homocoupling of an aryl chloride at 82 °C, which is a relatively low temperature when compared to regular Ullmann reaction temperatures. Also, NPPA was successfully employed in base-and heat free Suzuki reactions, including electron rich and poor aryl halides with heteroarylboronic acids in moderate yields.

Original languageEnglish (US)
Pages (from-to)690-693
Number of pages4
JournalTetrahedron Letters
Issue number3
StatePublished - Jan 15 2014
Externally publishedYes


  • Aryl-aryl coupling
  • Copper catalyzed
  • Homocoupling
  • N-Picolinamides
  • Ullmann-type coupling


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